An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

Marcus Baumann and
Ian R. Baxendale

Review
Published 30 Oct 2013

1242 Accesses

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Album
1. Graphical Abstract
2. Scheme 1: Scaled industrial processes for the synthesis of simple pyridines.
  
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3. Scheme 2: Synthesis of nicotinic acid from 2-methyl-5-ethylpyridine (1.11).
  
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4. Scheme 3: Synthesis of 3-picoline and nicotinic acid.
  
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5. Scheme 4: Synthesis of 3-picoline from 2-methylglutarodinitrile 1.19.
  
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6. Scheme 5: Picoline-based synthesis of clarinex (no yields reported).
  
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7. Scheme 6: Mode of action of proton-pump inhibitors and structures of the API’s.
  
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8. Scheme 7: Hantzsch-like route towards the pyridine rings in common proton pump inhibitors.
  
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9. Figure 1: Structures of rosiglitazone (1.40) and pioglitazone (1.41).
  
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10. Scheme 8: Synthesis of rosiglitazone.
  
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11. Scheme 9: Syntheses of 2-pyridones.
  
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12. Scheme 10: Synthesis and mechanism of 2-pyrone from malic acid.
  
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13. Scheme 11: Polymer-assisted synthesis of rosiglitazone.
  
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14. Scheme 12: Synthesis of pioglitazone.
  
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15. Scheme 13: Meerwein arylation reaction towards pioglitazone.
  
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16. Scheme 14: Route towards pioglitazone utilising tyrosine.
  
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17. Scheme 15: Route towards pioglitazone via Darzens ester formation.
  
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18. Scheme 16: Syntheses of the thiazolidinedione moiety.
  
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19. Scheme 17: Synthesis of etoricoxib utilising Negishi and Stille cross-coupling reactions.
  
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20. Scheme 18: Synthesis of etoricoxib via vinamidinium condensation.
  
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21. Figure 2: Structures of nalidixic acid, levofloxacin and moxifloxacin.
  
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22. Scheme 19: Synthesis of moxifloxacin.
  
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23. Scheme 20: Synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane 1.105.
  
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24. Scheme 21: Synthesis of levofloxacin.
  
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25. Scheme 22: Alternative approach to the levofloxacin core 1.125.
  
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26. Figure 3: Structures of nifedipine, amlodipine and clevidipine.
  
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27. Scheme 23: Mg₃N₂-mediated synthesis of nifedipine.
  
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28. Scheme 24: Synthesis of rac-amlodipine as besylate salt.
  
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29. Scheme 25: Aza Diels–Alder approach towards amlodipine.
  
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30. Scheme 26: Routes towards clevidipine.
  
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31. Figure 4: Examples of piperidine containing drugs.
  
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32. Figure 5: Discovery of tiagabine based on early leads.
  
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33. Scheme 27: Synthetic sequences to tiagabine.
  
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34. Figure 6: Structures of solifenacin (2.57) and muscarine (2.58).
  
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35. Scheme 28: Enantioselective synthesis of solifenacin.
  
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36. Figure 7: Structures of DPP-4 inhibitors of the gliptin-type.
  
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37. Scheme 29: Formation of inactive diketopiperazines from cis-rotameric precursors.
  
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38. Figure 8: Co-crystal structure of carmegliptin bound in the human DPP-4 active site (PDB 3kwf).
  
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39. Scheme 30: Improved route to carmegliptin.
  
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40. Figure 9: Structures of lamivudine and zidovudine.
  
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41. Scheme 31: Typical routes accessing uracil, thymine and cytosine.
  
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42. Scheme 32: Coupling between pyrimidones and riboses via the Vorbrüggen nucleosidation.
  
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43. Scheme 33: Synthesis of lamivudine.
  
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44. Scheme 34: Synthesis of raltegravir.
  
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45. Scheme 35: Mechanistic studies on the formation of 3.22.
  
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46. Figure 10: Structures of selected pyrimidine containing drugs.
  
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47. Scheme 36: General preparation of pyrimidines and dihydropyrimidones.
  
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48. Scheme 37: Synthesis of imatinib.
  
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49. Scheme 38: Flow synthesis of imatinib.
  
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50. Scheme 39: Syntheses of erlotinib.
  
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51. Scheme 40: Synthesis of erlotinib proceeding via Dimroth rearrangement.
  
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52. Scheme 41: Synthesis of lapatinib.
  
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53. Scheme 42: Synthesis of rosuvastatin.
  
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54. Scheme 43: Alternative preparation of the key aldehyde towards rosuvastatin.
  
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55. Figure 11: Structure comparison between nicotinic acetylcholine receptor agonists.
  
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56. Scheme 44: Syntheses of varenicline and its key building block 4.5.
  
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57. Scheme 45: Synthetic access to eszopiclone and brimonidine via quinoxaline intermediates.
  
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58. Figure 12: Bortezomib bound in an active site of the yeast 20S proteasome ([114], pdb 2F16).
  
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59. Scheme 46: Asymmetric synthesis of bortezomib.
  
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60. Figure 13: Structures of some prominent piperazine containing drugs.
  
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61. Figure 14: Structural comparison between the core of aplaviroc (4.35) and a type-1 β-turn (4.36).
  
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62. Scheme 47: Examplary synthesis of an aplaviroc analogue via the Ugi-MCR.
  
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63. Scheme 48: Syntheses of azelastine (5.1).
  
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64. Figure 15: Structures of captopril, enalapril and cilazapril.
  
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65. Scheme 49: Synthesis of cilazapril.
  
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66. Figure 16: Structures of lamotrigine, ceftriaxone and azapropazone.
  
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67. Scheme 50: Synthesis of lamotrigine.
  
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68. Scheme 51: Alternative synthesis of lamotrigine (no yields reported).
  
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69. Figure 17: Structural comparison between imiquimod and the related adenosine nucleoside.
  
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70. Scheme 52: Conventional synthesis of imiquimod (no yields reported).
  
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71. Scheme 53: Synthesis of imiquimod.
  
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72. Scheme 54: Synthesis of imiquimod via tetrazole formation (not all yields reported).
  
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73. Figure 18: Structures of various anti HIV-medications.
  
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74. Scheme 55: Synthesis of abacavir.
  
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75. Figure 19: Structures of diazepam compared to modern replacements.
  
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76. Scheme 56: Synthesis of ocinaplon.
  
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77. Scheme 57: Access to zaleplon and indiplon.
  
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78. Scheme 58: Different routes towards the required N-methylpyrazole 6.65 of sildenafil.
  
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79. Scheme 59: Polymer-supported reagents in the synthesis of key aminopyrazole 6.72.
  
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80. Scheme 60: Early synthetic route to sildenafil.
  
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81. Scheme 61: Convergent preparations of sildenafil.
  
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82. Figure 20: Comparison of the structures of sildenafil, tadalafil and vardenafil.
  
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83. Scheme 62: Short route to imidazotriazinones.
  
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84. Scheme 63: Alternative route towards vardenafils core imidazotriazinone (6.95).
  
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85. Scheme 64: Bayer’s approach to the vardenafil core.
  
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86. Scheme 65: Large scale synthesis of vardenafil.
  
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87. Scheme 66: Mode of action of temozolomide (6.105) as methylating agent.
  
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88. Scheme 67: Different routes to temozolomide.
  
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89. Scheme 68: Safer route towards temozolomide.
  
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90. Figure 21: Some unreported heterocyclic scaffolds in top market drugs.
  
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Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

Full Text

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

Marcus Baumann,
Ian R. Baxendale,
Steven V. Ley and
Nikzad Nikbin

Review
Published 18 Apr 2011

684 Accesses

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Album
1. Graphical Abstract
2. Figure 1: Structures of atorvastatin and other commercial statins.
  
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3. Figure 2: Structure of compactin.
  
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4. Scheme 1: Synthesis of pentasubstituted pyrroles.
  
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5. Scheme 2: [3 + 2] Cycloaddition to prepare 5-isopropylpyrroles.
  
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6. Scheme 3: Regiospecific [3 + 2] cycloaddition to prepare the pyrrole scaffold.
  
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7. Scheme 4: Formation of the pyrrole core of atorvastatin via [3 + 2] cycloaddition.
  
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8. Scheme 5: Formation of pyrrole 33 via the Paal–Knorr reaction.
  
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9. Scheme 6: Convergent synthesis towards atorvastatin.
  
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10. Figure 3: Binding pocket of sunitinib in the TRK KIT.
  
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11. Scheme 7: Synthesis of sunitinib.
  
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12. Scheme 8: Alternative synthesis of sunitinib.
  
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13. Scheme 9: Key steps in the syntheses of sumatriptan and zolmitriptan.
  
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14. Scheme 10: Introduction of the N,N-dimethylaminoethyl side chain.
  
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15. Scheme 11: Japp–Klingemann reaction in the synthesis of sumatriptan.
  
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16. Scheme 12: Synthesis of the intermediate sulfonyl chlorides 62 and 63.
  
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17. Scheme 13: Alternative introduction of the sulfonamide.
  
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18. Scheme 14: Negishi-type coupling to benzylic sulfonamides.
  
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19. Scheme 15: Heck reaction used to introduce the sulfonamide side chain of naratriptan.
  
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20. Scheme 16: Synthesis of the oxazolinone appendage of zolmitriptan.
  
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21. Scheme 17: Grandberg indole synthesis used in the preparation of rizatriptan.
  
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22. Scheme 18: Improved synthesis of rizatriptan.
  
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23. Scheme 19: Larock-type synthesis of rizatriptan.
  
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24. Scheme 20: Synthesis of eletriptan.
  
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25. Scheme 21: Heck coupling for the indole system in eletriptan.
  
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26. Scheme 22: Attempted Fischer indole synthesis of elatriptan.
  
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27. Scheme 23: Successful Fischer indole synthesis for eletriptan.
  
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28. Scheme 24: Mechanistic rationale for the Bischler–Möhlau reaction.
  
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29. Scheme 25: Bischler-type indole synthesis used in the fluvastatin sodium synthesis.
  
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30. Scheme 26: Palladium-mediated synthesis of ondansetron.
  
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31. Scheme 27: Fischer indole synthesis of ondansetron.
  
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32. Scheme 28: Optimised Pictet–Spengler reaction towards tadalafil.
  
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33. Figure 4: Structures of carvedilol 136 and propranolol 137.
  
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34. Scheme 29: Synthesis of the carbazole core of carvedilol.
  
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35. Scheme 30: Alternative syntheses of 4-hydroxy-9H-carbazole.
  
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36. Scheme 31: Convergent synthesis of etodolac.
  
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37. Scheme 32: Alternative synthesis of etodolac.
  
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38. Figure 5: Structures of imidazole-containing drugs.
  
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39. Scheme 33: Synthesis of functionalised imidazoles towards losartan.
  
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40. Scheme 34: Direct synthesis of the chlorinated imidazole in losartan.
  
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41. Scheme 35: Synthesis of trisubstituted imidazoles.
  
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42. Scheme 36: Preparation of the imidazole ring in olmesartan.
  
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43. Scheme 37: Synthesis of ondansetron.
  
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44. Scheme 38: Alternative route to ondansetron and its analogues.
  
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45. Scheme 39: Proton pump inhibitors and synthesis of esomeprazole.
  
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46. Scheme 40: Synthesis of benzimidazole core pantoprazole.
  
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47. Figure 6: Structure of rabeprazole 194.
  
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48. Scheme 41: Synthesis of candesartan.
  
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49. Scheme 42: Alternative access to the candesartan key intermediate 216.
  
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50. Scheme 43: .Medicinal chemistry route to telmisartan.
  
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51. Scheme 44: Improved synthesis of telmisartan.
  
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52. Scheme 45: Synthesis of zolpidem.
  
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53. Scheme 46: Copper-catalysed 3-component coupling towards zolpidem.
  
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54. Figure 7: Structure of celecoxib.
  
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55. Scheme 47: Preparation of celecoxib.
  
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56. Scheme 48: Alternative synthesis of celecoxib.
  
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57. Scheme 49: Regioselective access to celecoxib.
  
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58. Scheme 50: Synthesis of pazopanib.
  
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59. Scheme 51: Syntheses of anastrozole, rizatriptan and letrozole.
  
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60. Scheme 52: Regioselective synthesis of anastrozole.
  
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61. Scheme 53: Triazine-mediated triazole formation towards anastrozole.
  
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62. Scheme 54: Alternative routes to 1,2,4-triazoles.
  
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63. Scheme 55: Initial synthetic route to sitagliptin.
  
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64. Figure 8: Binding of sitagliptin within DPP-IV.
  
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65. Scheme 56: The process route to sitagliptin key intermediate 280.
  
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66. Scheme 57: Synthesis of maraviroc.
  
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67. Scheme 58: Synthesis of alprazolam.
  
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68. Scheme 59: The use of N-nitrosoamidine derivatives in the preparation of fused benzodiazepines.
  
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69. Figure 9: Structures of itraconazole, ravuconazole and voriconazole.
  
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70. Scheme 60: Synthesis of itraconazole.
  
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71. Scheme 61: Synthesis of rufinamide.
  
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72. Scheme 62: Representative tetrazole formation in valsartan.
  
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73. Figure 10: Structure of tetrazole containing olmesartan, candesartan and irbesartan.
  
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74. Scheme 63: Early stage introduction of the tetrazole in losartan.
  
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75. Scheme 64: Synthesis of cilostazol.
  
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76. Figure 11: Structure of cefdinir.
  
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77. Scheme 65: Semi-synthesis of cefdinir.
  
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78. Scheme 66: Thiazole syntheses towards ritonavir.
  
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79. Scheme 67: Synthesis towards pramipexole.
  
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80. Scheme 68: Alternative route to pramipexole.
  
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81. Scheme 69: Synthesis of famotidine.
  
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82. Scheme 70: Efficient synthesis of the hyperuricemic febuxostat.
  
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83. Scheme 71: Synthesis of ziprasidone.
  
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84. Figure 12: Structure of mometasone.
  
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85. Scheme 72: Industrial access to 2-furoic acid present in mometasone.
  
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86. Scheme 73: Synthesis of ranitidine from furfuryl alcohol.
  
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87. Scheme 74: Synthesis of nitrofurantoin.
  
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88. Scheme 75: Synthesis of benzofuran.
  
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89. Scheme 76: Synthesis of amiodarone.
  
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90. Scheme 77: Synthesis of raloxifene.
  
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91. Scheme 78: Alternative access to the benzo[b]thiophene core of raloxifene.
  
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92. Scheme 79: Gewald reaction in the synthesis of olanzapine.
  
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93. Scheme 80: Alternative synthesis of olanzapine.
  
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94. Figure 13: Access to simple thiophene-containing drugs.
  
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95. Scheme 81: Synthesis of clopidogrel.
  
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96. Scheme 82: Pictet–Spengler reaction in the preparation of tetrahydrothieno[3,2-c]pyridine (422).
  
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97. Scheme 83: Alternative synthesis of key intermediate 422.
  
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98. Figure 14: Co-crystal structures of timolol (left) and carazolol (right) in the β-adrenergic receptor.
  
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99. Scheme 84: Synthesis of timolol.
  
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100. Scheme 85: Synthesis of tizanidine 440.
  
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101. Scheme 86: Synthesis of leflunomide.
  
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102. Scheme 87: Synthesis of sulfamethoxazole.
  
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103. Scheme 88: Synthesis of risperidone.
  
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104. Figure 15: Relative abundance of selected transformations.
  
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105. Figure 16: The abundance of heterocycles within top 200 drugs (5-membered rings).
  
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Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

Full Text

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

Marcus Baumann and
Ian R. Baxendale

Review
Published 17 Jul 2015

658 Accesses

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Album
1. Graphical Abstract
2. Figure 1: Pharmaceutical structures targeted in early flow syntheses.
  
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3. Scheme 1: Flow synthesis of 6-hydroxybuspirone (9). Inserted photograph reprinted with permission from [45]. Copy...
  
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4. Figure 2: Configuration of a baffled reactor tube (left) and its schematic working principle (right).
  
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5. Scheme 2: McQuade’s flow synthesis of ibuprofen (16).
  
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6. Scheme 3: Jamison’s flow synthesis of ibuprofen sodium salt (17).
  
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7. Scheme 4: Flow synthesis of imatinib (23).
  
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8. Scheme 5: Flow synthesis of the potent 5HT1B antagonist 28.
  
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9. Scheme 6: Flow synthesis of a selective δ-opioid receptor agonist 33.
  
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10. Scheme 7: Flow synthesis of a casein kinase I inhibitor library (38).
  
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11. Scheme 8: Flow synthesis of fluoxetine (46).
  
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12. Scheme 9: Flow synthesis of artemisinin (55).
  
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13. Scheme 10: Telescoped flow synthesis of artemisinin (55) and derivatives (62–64).
  
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14. Scheme 11: Flow approach towards AZD6906 (65).
  
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15. Scheme 12: Pilot scale flow synthesis of key intermediate 73.
  
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16. Scheme 13: Semi-flow synthesis of vildagliptine (77).
  
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17. Scheme 14: Pilot scale asymmetric flow hydrogenation towards 83. Inserted photograph reprinted with permission...
  
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18. Figure 3: Schematic representation of the ‘tube-in-tube’ reactor.
  
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19. Scheme 15: Flow synthesis of fanetizole (87) via tube-in-tube system.
  
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20. Scheme 16: Flow synthesis of diphenhydramine^.HCl (92).
  
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21. Scheme 17: Flow synthesis of rufinamide (95).
  
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22. Scheme 18: Large scale flow synthesis of rufinamide precursor 102.
  
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23. Scheme 19: First stage in the flow synthesis of meclinertant (103).
  
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24. Scheme 20: Completion of the flow synthesis of meclinertant (103).
  
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25. Scheme 21: Flow synthesis of olanzapine (121) utilising inductive heating techniques.
  
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26. Scheme 22: Flow synthesis of amitriptyline·HCl (127).
  
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27. Scheme 23: Flow synthesis of E/Z-tamoxifen (132) using peristaltic pumping modules.
  
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28. Figure 4: Container sized portable mini factory (photograph credit: INVITE GmbH, Leverkusen Germany).
  
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29. Scheme 24: Flow synthesis of imidazo[1,2-a]pyridines 136 linked to frontal affinity chromatography (FAC).
  
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30. Figure 5: Structures of zolpidem (142) and alpidem (143).
  
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31. Scheme 25: Synthesis and screening loops in the discovery of new Abl kinase inhibitors.
  
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32. Figure 6: Schotten–Baumann approach towards LY573636^.Na (147).
  
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33. Scheme 26: Pilot scale flow synthesis of LY2886721 (146).
  
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34. Scheme 27: Continuous flow manufacture of alikiren hemifumarate 152.
  
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Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

Full Text

Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

Andreas H. Heindl and
Hermann A. Wegner

Full Research Paper
Published 03 Jan 2020

559 Accesses

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1. Graphical Abstract
2. Figure 1: 1,3,5-Tris(arylazo)benzenes as individually switchable multistate photoswitches: previous [11,12] and pres...
  
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3. Scheme 1: Synthetic strategy towards 1,3,5-tris(arylazo)benzenes 3 based on consecutive Baeyer–Mills reaction...
  
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4. Scheme 2: Preparation of tris(arylazo)benzenes 3 by Pd-catalyzed cross-coupling reactions of N-Boc-arylhydraz...
  
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5. Scheme 3: Synthesis of azobenzene building block 8.
  
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6. Scheme 4: Synthesis of 1,3-bis(4-methoxyphenylazo)-5-phenylazobenzene (14).
  
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7. Scheme 5: Synthesis of unsymmetrical tris(arylazo)benzenes 3a/3b using Pd-catalyzed coupling reactions and Cu...
  
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8. Scheme 6: Coupling reactions of 15 with the corresponding arylhydrazides to access monocoupled (16a/16b) and ...
  
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9. Figure 2: a) UV–vis spectra of tris(arylazo)benzenes 3a/3b in ethanol. b) Reversible photoisomerization of 3a...
  
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Supp. Info

Beilstein J. Org. Chem. 2020, 16, 22–31, doi:10.3762/bjoc.16.4

Full Text

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

Magnus Rueping and
Boris J. Nachtsheim

Review
Published 20 Jan 2010

532 Accesses

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Album
1. Graphical Abstract
2. Scheme 1: AlCl₃-mediated reaction between amyl chloride and benzene as developed by Friedel and Crafts.
  
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3. Figure 1: Most often used metal salts for catalytic FC alkylations and hydroarylations of arenes.
  
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4. Figure 2: 1,1-diarylalkanes with biological activity.
  
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5. Scheme 2: Alkylating reagents and side products produced.
  
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6. Scheme 3: Initially reported TeCl₄-mediated FC alkylation of 1-penylethanol with toluene.
  
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7. Scheme 4: Sc(OTf)₃-catalyzed FC benzylation of arenes.
  
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8. Scheme 5: Reductive FC alkylation of arenes with arenecarbaldehydes.
  
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9. Scheme 6: Iron(III)-catalyzed FC benzylation of arenes and heteroarenes.
  
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10. Scheme 7: A gold(III)-catalyzed route to beclobrate.
  
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11. Scheme 8: Catalytic FC-type alkylations of 1,3-dicarbonyl compounds.
  
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12. Scheme 9: Iron(III)-catalyzed synthesis of phenprocoumon.
  
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13. Scheme 10: Bi(OTf)₃-catalyzed FC alkylation of benzyl alcohols developed by Rueping et al.
  
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14. Scheme 11: (A) Bi(OTf)₃-catalyzed intramolecular FC alkylation as an efficient route to substituted fulvenes. ...
  
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15. Scheme 12: FC-type glycosylation of 1,2-dimethylindole and trimethoxybenzene.
  
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16. Scheme 13: FC alkylation with highly reactive ferrocenyl- and benzyl alcohols. The reaction proceeds even with...
  
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17. Scheme 14: Reductive FC alkylation of arenes with benzaldehyde and acetophenone catalyzed by the Ir-carbene co...
  
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18. Scheme 15: Formal synthesis of 1,1-diarylalkanes from benzyl alcohols and styrenes.
  
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19. Scheme 16: (A) Mo-catalyzed hydroarylation of styrenes and cyclohexenes. (B) Hydroalkylation–cyclization casca...
  
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20. Scheme 17: Bi(III)-catalyzed hydroarylation of styrenes with arenes and heteroarenes.
  
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21. Scheme 18: BiCl₃-catalyzed ene/FC alkylation reaction cascade – A fast access to highly arylated dihydroindene...
  
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22. Scheme 19: Au(I)/Ag(I)-catalyzed hydroarylation of indoles with styrenes, aliphatic and cyclic alkenes.
  
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23. Scheme 20: First transition-metal-catalyzed ortho-hydroarylation developed by Beller et al.
  
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24. Scheme 21: (A) Ti(IV)-mediated rearrangement of an N-benzylated aniline to the corresponding ortho-alkylated a...
  
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25. Scheme 22: Dibenzylation of aniline gives potentially useful amine-based ligands in a one-step procedure.
  
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26. Scheme 23: FC-type alkylations with allyl alcohols as alkylating reagents – linear vs. branched product format...
  
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27. Scheme 24: (A) First catalytic FC allylation and cinnamylation using allyl alcohols and its derivatives. (B) E...
  
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28. Scheme 25: FC allylation/cyclization reaction yielding substituted chromanes.
  
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29. Scheme 26: Synthesis of (all-rac)-α-tocopherol utilizing Lewis- and strong Brønsted-acids.
  
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30. Scheme 27: Au(III)-catalyzed cinnamylation of arenes.
  
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31. Scheme 28: “Exhaustive” allylation of benzene-1,3,5-triol.
  
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32. Scheme 29: Palladium-catalyzed allylation of indole.
  
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33. Scheme 30: Pd-catalyzed synthesis of pyrroloindoles from L-tryptophane.
  
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34. Scheme 31: Ru(IV)-catalyzed allylation of indole and pyrroles with unique regioselectivity.
  
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35. Scheme 32: Silver(I)-catalyzed intramolecular FC-type allylation of arenes and heteroarenes.
  
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36. Scheme 33: FC-type alkylations of arenes using propargyl alcohols.
  
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37. Scheme 34: (A) Propargylation of arenes with stoichiometric amounts of the Ru-allenylidene complex 86. (B) Fir...
  
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38. Scheme 35: Diruthenium-catalyzed formation of chromenes and 1H-naphtho[2,1-b]pyrans.
  
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39. Scheme 36: Rhenium(V)-catalyzed FC propargylations as a first step in the total synthesis of podophyllotoxin, ...
  
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40. Scheme 37: Scandium-catalyzed arylation of 3-sulfanyl- and 3-selanylpropargyl alcohols.
  
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41. Scheme 38: Synthesis of 1,3-diarylpropynes via direct coupling of propargyl trichloracetimidates and arenes.
  
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42. Scheme 39: Diastereoselective substitutions of benzyl alcohols.
  
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43. Scheme 40: (A) First diastereoselective FC alkylations developed by Bach et al. (B) anti-Selective FC alkylati...
  
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44. Scheme 41: Diastereoselective AuCl₃-catalyzed FC alkylation.
  
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45. Scheme 42: Bi(OTf)₃-catalyzed alkylation of α-chiral benzyl acetates with silyl enol ethers.
  
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46. Scheme 43: Bi(OTf)₃-catalyzed diastereoselective substitution of propargyl acetates.
  
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47. Scheme 44: Nucelophilic substitution of enantioenriched ferrocenyl alcohols.
  
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48. Scheme 45: First catalytic enantioselective propargylation of arenes.
  
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Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6

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Synthesis and characterization of bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives

David Martínez-López,
Amirhossein Babalhavaeji,
Diego Sampedro and
G. Andrew Woolley

Full Research Paper
Published 30 Dec 2019

508 Accesses

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Album
1. Graphical Abstract
2. Figure 1: Structures of azonium ions studied.
  
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3. Figure 2: a) Structures of model compounds used for computations (see Experimental section; in calculations, ...
  
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4. Scheme 1: Synthesis of bis(4-amino-2-bromo-6-methoxy)azobenzene compounds.
  
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5. Figure 3: a) UV–vis spectra of 4 in DCM (ca. 15 µM) at the PSS and 440 nm irradiation (thick dotted line; ca....
  
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6. Figure 4: a) UV–vis spectra of 5 in aqueous solution (c ≈ 15 µM, 5% methanol, pH 7) at the PSS and 440 nm irr...
  
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Beilstein J. Org. Chem. 2019, 15, 3000–3008, doi:10.3762/bjoc.15.296

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The chemistry of amine radical cations produced by visible light photoredox catalysis

Jie Hu,
Jiang Wang,
Theresa H. Nguyen and
Nan Zheng

Review
Published 01 Oct 2013

499 Accesses

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Album
1. Graphical Abstract
2. Scheme 1: Amine radical cations’ mode of reactivity.
  
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3. Scheme 2: Reductive quenching of photoexcited Ru complexes by Et₃N.
  
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4. Scheme 3: Photoredox aza-Henry reaction.
  
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5. Scheme 4: Formation of iminium ions using BrCCl₃ as stoichiometric oxidant.
  
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6. Scheme 5: Oxidative functionalization of N-aryltetrahydroisoquinolines using Eosin Y.
  
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7. Scheme 6: Synthetic and mechanistic studies of Eosin Y-catalyzed aza-Henry reaction.
  
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8. Scheme 7: Oxidative functionalization of N-aryltetrahydroisoquinolines using RB and GO.
  
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9. Scheme 8: Merging Ru-based photoredox catalysis and Lewis base catalysis for the Mannich reaction.
  
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10. Scheme 9: Merging Au-based photoredox catalysis and Lewis base catalysis for the Mannich reaction.
  
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11. Scheme 10: Merging Ru-based photoredox catalysis and Cu-catalyzed alkynylation reaction.
  
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12. Scheme 11: Merging Ru-based photoredox catalysis and NHC catalysis.
  
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13. Scheme 12: 1,3-Dipolar cycloaddition of photogenically formed azomethine ylides.
  
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14. Scheme 13: Plausible mechanism for photoredox 1,3-dipolar cycloaddition.
  
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15. Scheme 14: Photoredox-catalyzed cascade reaction for the synthesis of fused isoxazolidines.
  
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16. Scheme 15: Plausible mechanism for the photoredox-catalyzed cascade reaction.
  
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17. Scheme 16: Photoredox-catalyzed α-arylation of glycine derivatives.
  
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18. Scheme 17: Photoredox-catalyzed α-arylation of amides.
  
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19. Scheme 18: Intramolecular interception of iminium ions by sulfonamides.
  
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20. Scheme 19: Intramolecular interception of iminium ions by alcohols and sulfonamides.
  
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21. Scheme 20: Intermolecular interception of iminium ions by phosphites.
  
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22. Scheme 21: Photoredox-catalyzed oxidative phosphonylation by Eosin Y.
  
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23. Scheme 22: Conjugated addition of α-amino radicals to Michael acceptors.
  
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24. Scheme 23: Conjugated addition of α-amino radicals to Michael acceptors assisted by a Brønsted acid.
  
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25. Scheme 24: Conjugated addition of α-amino radicals derived from anilines to Michael acceptors.
  
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26. Scheme 25: Oxygen switch between two pathways involving α-amino radicals.
  
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27. Scheme 26: Interception of α-amino radicals by azodicarboxylates.
  
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28. Scheme 27: α-Arylation of amines.
  
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29. Scheme 28: Plausible mechanism for α-arylation of amines.
  
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30. Scheme 29: Photoinduced C–C bond cleavage of tertiary amines.
  
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31. Scheme 30: Photoredox cleavage of C–C bonds of 1,2-diamines.
  
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32. Scheme 31: Proposed mechanism photoredox cleavage of C–C bonds.
  
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33. Scheme 32: Intermolecular [3 + 2] annulation of cyclopropylamines with olefins.
  
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34. Scheme 33: Proposed mechanism for intermolecular [3 + 2] annulation.
  
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35. Scheme 34: Photoinduced clevage of N–N bonds of aromatic hydrazines and hydrazides.
  
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Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234

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Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol

María C. Mollo,
Natalia B. Kilimciler,
Juan A. Bisceglia and
Liliana R. Orelli

Full Research Paper
Published 06 Jan 2020

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Album
1. Graphical Abstract
2. Scheme 1: Chemical shift data for N-thiobenzoylpiperidine and compound 4a.
  
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3. Scheme 2: PPSE promoted ring closure reactions of amido- and thioamido alcohols.
  
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Beilstein J. Org. Chem. 2020, 16, 32–38, doi:10.3762/bjoc.16.5

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Computational methods in drug discovery

Sumudu P. Leelananda and
Steffen Lindert

Review
Published 12 Dec 2016

428 Accesses

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Album
1. Graphical Abstract
2. Figure 1: Schematic representation of a computer-aided drug discovery (CADD) pipeline. CADD methods are broad...
  
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3. Figure 2: FDA approved drugs Saquinavir and Amprenavir for the treatment of HIV infections. (a) The structure...
  
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4. Figure 3: (a) The crystal structure showing the binding of Dorzolamide (orange) to carbonic anhydrase II (pur...
  
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5. Figure 4: The best ligand binding site identified by SiteHound in HIV-1 protease. The ligand binding pocket i...
  
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6. Figure 5: Binding mode prediction. The known inhibitor Dorzolamide is docked into Carbonic anhydrase II cryst...
  
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7. Figure 6: The molecular structure of Raltegravir. Raltegravir is an FDA approved drug used in the treatment o...
  
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8. Figure 7: An example alchemical thermodynamic cycle for a protein–ligand binding free energy calculation. The...
  
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9. Figure 8: Schematic diagram showing the steps involved in QSAR. Known drug molecule activity and descriptor d...
  
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10. Figure 9: A few drugs discovered with the help of ligand-based drug discovery tools. (a) Zolmitriptan: used a...
  
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Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267

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A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

Munmun Ghosh,
Valmik S. Shinde and
Magnus Rueping

Review
Published 13 Nov 2019

410 Accesses

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Album
1. Graphical Abstract
2. Figure 1: General classification of asymmetric electroorganic reactions.
  
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3. Scheme 1: Asymmetric reduction of 4-acetylpyridine using a modified graphite cathode.
  
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4. Scheme 2: Asymmetric hydrogenation of ketones using Raney nickel powder electrodes modified with optically ac...
  
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5. Scheme 3: Asymmetric reduction of prochiral activated olefins with a poly-ʟ-valine-coated graphite cathode.
  
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6. Scheme 4: Asymmetric reduction of prochiral carbonyl compounds, oximes and gem-dibromides on a poly-ʟ-valine-...
  
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7. Scheme 5: Asymmetric hydrogenation of prochiral ketones with poly[Ru^III(L)₂Cl₂]⁺-modified carbon felt cathode...
  
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8. Scheme 6: Asymmetric hydrogenation of α-keto esters using chiral polypyrrole film-coated cathode incorporated...
  
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9. Scheme 7: Quinidine and cinchonidine alkaloid-induced asymmetric electroreduction of acetophenone.
  
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10. Scheme 8: Asymmetric electroreduction of 4- and 2-acetylpyridines at a mercury cathode in the presence of a c...
  
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11. Scheme 9: Enantioselective reduction of 4-methylcoumarin in the presence of catalytic yohimbine.
  
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12. Scheme 10: Cinchonine-induced asymmetric electrocarboxylation of 4-methylpropiophenone.
  
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13. Scheme 11: Enantioselective hydrogenation of methyl benzoylformate using an alkaloid entrapped silver cathode.
  
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14. Scheme 12: Alkaloid-induced enantioselective hydrogenation using a Cu nanoparticle cathode.
  
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15. Scheme 13: Alkaloid-induced enantioselective hydrogenation of aromatic ketones using a bimetallic Pt@Cu cathod...
  
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16. Scheme 14: Enantioselective reduction of ketones at mercury cathode using N,N'-dimethylquininium tetrafluorobo...
  
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17. Scheme 15: Asymmetric synthesis of an amino acid using an electrode modified with amino acid oxidase and elect...
  
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18. Scheme 16: Asymmetric oxidation of p-tolyl methyl sulfide using chemically modified graphite anode.
  
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19. Scheme 17: Asymmetric oxidation of unsymmetric sulfides using poly(amino acid)-coated electrodes.
  
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20. Scheme 18: Enantioselective, electocatalytic oxidative coupling on TEMPO-modified graphite felt electrode in t...
  
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21. Scheme 19: Asymmetric electrocatalytic oxidation of racemic alcohols on a TEMPO-modified graphite felt electro...
  
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22. Scheme 20: Asymmetric electrocatalytic lactonization of diols on TEMPO-modified graphite felt electrodes.
  
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23. Scheme 21: Asymmetric electrochemical pinacolization in a chiral solvent.
  
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24. Scheme 22: Asymmetric electroreduction using a chiral supporting electrolyte.
  
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25. Scheme 23: Asymmetric anodic oxidation of enol acetates using chiral supporting electrolytes.
  
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26. Scheme 24: Kinetic resolution of primary amines using a chiral N-oxyl radical mediator.
  
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27. Scheme 25: Chiral N-oxyl-radical-mediated kinetic resolution of secondary alcohols via electrochemical oxidati...
  
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28. Scheme 26: Chiral iodoarene-mediated asymmetric electrochemical lactonization.
  
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29. Scheme 27: Os-catalyzed electrochemical asymmetric dihydroxylation of olefins using the Sharpless ligand and i...
  
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30. Scheme 28: Asymmetric electrochemical epoxidation of olefins catalyzed by a chiral Mn-salen complex.
  
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31. Scheme 29: Asymmetric electrooxidation of 1,2-diols, and amino alcohols using a chiral copper catalyst.
  
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32. Scheme 30: Mechanism of asymmetric electrooxidation of 1,2-diols, and amino alcohols using a chiral copper cat...
  
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33. Scheme 31: Enantioselective electrocarboxylation catalyzed by an electrogenerated chiral [Co^I(salen)]⁻ complex....
  
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34. Scheme 32: Asymmetric oxidative cross coupling of 2-acylimidazoles with silyl enol ethers.
  
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35. Scheme 33: Ni-catalyzed asymmetric electroreductive cleavage of allylic β-keto ester 89.
  
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36. Scheme 34: Asymmetric alkylation using a combination of electrosynthesis and a chiral Ni catalyst.
  
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37. Scheme 35: Mechanism of asymmetric alkylation using a combination of electrosynthesis and a chiral Ni catalyst....
  
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38. Scheme 36: Asymmetric epoxidation by electrogenerated percarbonate and persulfate ions in the presence of chir...
  
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39. Scheme 37: α-Oxyamination of aldehydes via anodic oxidation catalyzed by chiral secondary amines.
  
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40. Scheme 38: The α-alkylation of aldehydes via anodic oxidation catalyzed by chiral secondary amines.
  
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41. Scheme 39: Mechanism of α-alkylation of aldehydes via anodic oxidation catalyzed by chiral secondary amines.
  
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42. Scheme 40: Electrochemical chiral secondary amine-catalyzed intermolecular α-arylation of aldehydes.
  
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43. Scheme 41: Mechanism of electrochemical chiral secondary amine-catalyzed intermolecular α-arylation of aldehyd...
  
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44. Scheme 42: Asymmetric cross-dehydrogenative coupling of tertiary amines with simple ketones via an electrochem...
  
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45. Scheme 43: Electroenzymatic asymmetric reduction using enoate reductase.
  
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46. Scheme 44: Assymetric reduction using alcohol dehydrogenase as the electrocatalyst.
  
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47. Scheme 45: Asymmetric electroreduction catalyzed by thermophilic NAD-dependent alcohol dehydrogenase.
  
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48. Scheme 46: Asymmetric epoxidation of styrene by electrochemical regeneration of flavin-dependent monooxygenase....
  
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49. Scheme 47: Asymmetric electroreduction using a chloroperoxidase catalyst.
  
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50. Scheme 48: Asymmetric electrochemical transformation mediated by hydrophobic vitamin B12.
  
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51. Scheme 49: Diastereoselective cathodic reduction of phenylglyoxalic acids substituted with amines as chiral au...
  
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52. Scheme 50: Ni-catalyzed asymmetric electroreductive cross coupling of aryl halides with α-chloropropanoic acid...
  
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53. Scheme 51: Electrochemical Mannich addition of silyloxyfuran to in situ-generated N-acyliminium ions.
  
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54. Scheme 52: Stereoselective electroreductive homodimerization of cinnamates attached to a camphor-derived chira...
  
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55. Scheme 53: Diastereoselective electrochemical carboxylation of chiral α-bromocarboxylic acid derivatives.
  
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56. Scheme 54: Electrocatalytic stereoselective conjugate addition of chiral β-dicarbonyl compounds to methyl viny...
  
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57. Scheme 55: Stereoselective electrochemical carboxylation of chiral cinnamic acid derivatives under a CO₂ atmos...
  
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58. Scheme 56: Electrochemical diastereoselective α-alkylation of pyrrolidines attached with phosphorus-derived ch...
  
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59. Scheme 57: Electrogenerated cyanomethyl anion-induced synthesis of chiral cis-β-lactams from amides bearing ch...
  
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60. Scheme 58: Diastereoselective anodic oxidation followed by intramolecular cyclization of ω-hydroxyl amides bea...
  
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61. Scheme 59: Electrochemical deprotonation of Ni(II) glycinate containing (S)-BPB as a chiral auxiliary: diaster...
  
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62. Scheme 60: Enantioselective electroreductive coupling of diaryl ketones with α,β-unsaturated carbonyl compound...
  
  Jump to Scheme 60
63. Scheme 61: Asymmetric total synthesis of ropivacaine and its analogues using a electroorganic reaction as a ke...
  
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64. Scheme 62: Asymmetric total synthesis of (−)-crispine A and its natural enantiomer via anodic cyanation of tet...
  
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65. Scheme 63: Asymmetric oxidative electrodimerization of cinnamic acid derivatives as key step for the synthesis...
  
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Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

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