Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Shivani Gulati,
Stephy Elza John and
Nagula Shankaraiah

Review
Published 19 Apr 2021

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1. Graphical Abstract
2. Figure 1: Marketed drugs with acridine moiety.
  
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3. Scheme 1: Synthesis of 4-arylacridinediones.
  
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4. Scheme 2: Proposed mechanism for acridinedione synthesis.
  
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5. Scheme 3: Synthesis of tetrahydrodibenzoacridinones.
  
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6. Scheme 4: Synthesis of naphthoacridines.
  
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7. Scheme 5: Plausible mechanism for naphthoacridines.
  
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8. Figure 2: Benzoazepines based potent molecules.
  
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9. Scheme 6: Synthesis of azepinone.
  
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10. Scheme 7: Proposed mechanism for azepinone formation.
  
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11. Scheme 8: Synthesis of benzoazulenen-1-one derivatives.
  
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12. Scheme 9: Proposed mechanism for benzoazulene-1-one synthesis.
  
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13. Figure 3: Indole-containing pharmacologically active molecules.
  
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14. Scheme 10: Synthesis of functionalized indoles.
  
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15. Scheme 11: Plausible mechanism for the synthesis of functionalized indoles.
  
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16. Scheme 12: Synthesis of spirooxindoles.
  
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17. Scheme 13: Synthesis of substituted spirooxindoles.
  
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18. Scheme 14: Plausible mechanism for the synthesis of substituted spirooxindoles.
  
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19. Scheme 15: Synthesis of pyrrolidinyl spirooxindoles.
  
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20. Scheme 16: Proposed mechanism for pyrrolidinyl spirooxindoles.
  
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21. Figure 4: Pyran-containing biologically active molecules.
  
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22. Scheme 17: Synthesis of functionalized benzopyrans.
  
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23. Scheme 18: Plausible mechanism for synthesis of benzopyran.
  
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24. Scheme 19: Synthesis of indoline-spiro-fused pyran derivatives.
  
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25. Scheme 20: Proposed mechanism for indoline-spiro-fused pyran.
  
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26. Scheme 21: Synthesis of substituted naphthopyrans.
  
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27. Figure 5: Marketed drugs with pyrrole ring.
  
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28. Scheme 22: Synthesis of tetra-substituted pyrroles.
  
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29. Scheme 23: Mechanism for silica-supported PPA-SiO₂-catalyzed pyrrole synthesis.
  
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30. Scheme 24: Synthesis of pyrrolo[1,10]-phenanthrolines.
  
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31. Scheme 25: Proposed mechanism for pyrrolo[1,10]-phenanthrolines.
  
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32. Figure 6: Marketed drugs and molecules containing pyrimidine and pyrimidinones skeletons.
  
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33. Scheme 26: MWA-MCR pyrimidinone synthesis.
  
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34. Scheme 27: Two proposed mechanisms for pyrimidinone synthesis.
  
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35. Scheme 28: MWA multicomponent synthesis of dihydropyrimidinones.
  
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36. Scheme 29: Proposed mechanism for dihydropyrimidinones.
  
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37. Figure 7: Biologically active fused pyrimidines.
  
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38. Scheme 30: MWA- MCR for the synthesis of pyrrolo[2,3-d]pyrimidines.
  
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39. Scheme 31: Proposed mechanism for pyrrolo[2,3-d]pyrimidines.
  
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40. Scheme 32: Synthesis of substituted pyrrolo[2,3-d]pyrimidine-2,4-diones.
  
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41. Scheme 33: Probable pathway for pyrrolo[2,3-d]pyrimidine-2,4-diones.
  
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42. Scheme 34: Synthesis of pyridopyrimidines.
  
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43. Scheme 35: Plausible mechanism for the synthesis of pyridopyrimidines.
  
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44. Scheme 36: Synthesis of dihydropyridopyrimidine and dihydropyrazolopyridine.
  
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45. Scheme 37: Proposed mechanism for the formation of dihydropyridopyrimidine.
  
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46. Scheme 38: Synthesis of thiopyrano[4,3-d]pyrimidines.
  
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47. Scheme 39: Plausible mechanism for the synthesis of thiopyrano[4,3-d]pyrimidines.
  
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48. Scheme 40: Synthesis of decorated imidazopyrimidines.
  
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49. Scheme 41: Proposed mechanism for imidazopyrimidine synthesis.
  
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50. Figure 8: Pharmacologically active molecules containing purine bases.
  
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51. Scheme 42: Synthesis of aza-adenines.
  
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52. Scheme 43: Synthesis of 5-aza-7-deazapurines.
  
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53. Scheme 44: Proposed mechanism for deazapurines synthesis.
  
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54. Figure 9: Biologically active molecules containing pyridine moiety.
  
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55. Scheme 45: Synthesis of steroidal pyridines.
  
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56. Scheme 46: Proposed mechanism for steroidal pyridine.
  
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57. Scheme 47: Synthesis of N-alkylated 2-pyridones.
  
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58. Scheme 48: Two possible mechanisms for pyridone synthesis.
  
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59. Scheme 49: Synthesis of pyridone derivatives.
  
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60. Scheme 50: Postulated mechanism for synthesis of pyridone.
  
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61. Figure 10: Biologically active fused pyridines.
  
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62. Scheme 51: Benzimidazole-imidazo[1,2-a]pyridines synthesis.
  
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63. Scheme 52: Mechanism for the synthesis of benzimidazole-imidazo[1,2-a]pyridines.
  
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64. Scheme 53: Synthesis of pyrazolo[3,4-b]pyridine-5-spirocycloalkanedione derivatives.
  
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65. Scheme 54: Proposed mechanism for spiro-pyridines.
  
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66. Scheme 55: Functionalized macrocyclane-fused pyrazolo[3,4-b]pyridine derivatives.
  
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67. Scheme 56: Mechanism postulated for macrocyclane-fused pyrazolo[3,4-b]pyridine.
  
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68. Scheme 57: Generation of pyrazolo[3,4-b]pyridines.
  
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69. Scheme 58: Proposed mechanism for the synthesis of pyrazolo[3,4-b]pyridines.
  
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70. Scheme 59: Proposed mechanism for the synthesis of azepinoindole.
  
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71. Figure 11: Pharmaceutically important molecules with quinoline moiety.
  
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72. Scheme 60: Povarov-mediated quinoline synthesis.
  
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73. Scheme 61: Proposed mechanism for Povarov reaction.
  
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74. Scheme 62: Synthesis of pyrazoloquinoline.
  
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75. Scheme 63: Plausible mechanism for pyrazoloquinoline synthesis.
  
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76. Figure 12: Quinazolinones as pharmacologically significant scaffolds.
  
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77. Scheme 64: Four-component reaction for dihydroquinazolinone.
  
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78. Scheme 65: Proposed mechanism for dihydroquinazolinones.
  
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79. Scheme 66: Synthesis purine quinazolinone and PI3K-δ inhibitor.
  
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80. Scheme 67: Synthesis of fused benzothiazolo/benzoimidazoloquinazolinones.
  
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81. Scheme 68: Proposed mechanism for fused benzothiazolo/benzoimidazoloquinazolinones.
  
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82. Scheme 69: On-water reaction for synthesis of thiazoloquinazolinone.
  
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83. Scheme 70: Proposed mechanism for the thiazoloquinazolinone synthesis.
  
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84. Scheme 71: β-Cyclodextrin-mediated synthesis of indoloquinazolinediones.
  
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85. Scheme 72: Proposed mechanism for synthesis of indoloquinazolinediones.
  
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86. Figure 13: Triazoles-containing marketted drugs and pharmacologically active molecules.
  
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87. Scheme 73: Cu(I) DAPTA-catalyzed 1,2,3-triazole formation.
  
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88. Scheme 74: Mechanism for Cu(I) DAPTA-catalyzed triazole formation.
  
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89. Scheme 75: Synthesis of β-hydroxy-1,2,3-triazole.
  
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90. Scheme 76: Proposed mechanism for synthesis of β-hydroxy-1,2,3-triazoles.
  
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91. Scheme 77: Synthesis of bis-1,2,4-triazoles.
  
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92. Scheme 78: Proposed mechanism for bis-1,2,4-triazoles synthesis.
  
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93. Figure 14: Thiazole containing drugs.
  
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94. Scheme 79: Synthesis of a substituted thiazole ring.
  
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95. Scheme 80: Synthesis of pyrazolothiazoles.
  
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96. Figure 15: Chromene containing drugs.
  
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97. Scheme 81: Magnetic nanocatalyst-mediated aminochromene synthesis.
  
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98. Scheme 82: Proposed mechanism for the synthesis of chromenes.
  
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Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

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Synthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy

Carl Recsei and
Yaniv Barda

Letter
Published 12 Apr 2021

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1. Graphical Abstract
2. Scheme 1: Retrosynthesis of compound 1.
  
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3. Scheme 2: Reported bis(aryloxy)fluoromethane syntheses. Reagents and conditions: (a) Cl₂FCH, NaOH, 1,4-dioxan...
  
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4. Scheme 3: Attempted synthesis of 4. Reagents and conditions: (a) Ca(OH)₂, 1,4-dioxane/water, reflux, 72 h, 5%...
  
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5. Scheme 4: Synthesis of 10. Reagents and conditions: (a) BrFCHCO₂Et, Cs₂CO₃, DMF, 35 °C, 16 h then H₂O, 35 °C,...
  
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6. Scheme 5: Synthesis of 1. Reagents and conditions: (a) 1,3-dibromo-5,5-dimethylhydantoin, benzoyl peroxide, (...
  
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7. Scheme 6: Synthesis of 11–13. Reagents and conditions: ArOH (1.3 mmol), Br₂FCH (1.3 mmol), KOH (4 mmol), MeCN...
  
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8. Scheme 7: Proposed mechanism for the formation of compound 11.
  
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Beilstein J. Org. Chem. 2021, 17, 813–818, doi:10.3762/bjoc.17.70

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A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

Ke Wu,
Yichen Ling,
An Ding,
Liqun Jin,
Nan Sun,
Baoxiang Hu,
Zhenlu Shen and
Xinquan Hu

Full Research Paper
Published 09 Apr 2021

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1. Graphical Abstract
2. Figure 1: Generation of the six-membered byproduct A from thionation reactions using Lawesson’s reagent.
  
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3. Figure 2: Work-up procedure for the reaction with LR.
  
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4. Figure 3: Modified process for the synthesis of 2e via phase separation.
  
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5. Scheme 1: Modified process for the synthesis of pincer ligand 4.
  
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6. Scheme 2: Modified process for the synthesis of pincer-type ligand 6.
  
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Beilstein J. Org. Chem. 2021, 17, 805–812, doi:10.3762/bjoc.17.69

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Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

David Weinzierl and
Mario Waser

Letter
Published 08 Apr 2021

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1. Graphical Abstract
2. Scheme 1: Overview about established methods to access enantioenriched 2 and the herein investigated kinetic ...
  
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3. Scheme 2: Use of alternative acylating agents 4 for the kinetic resolution of rac-2.
  
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Beilstein J. Org. Chem. 2021, 17, 800–804, doi:10.3762/bjoc.17.68

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Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

Zhonglie Yang,
Yutong Liu,
Kun Cao,
Xiaobin Zhang,
Hezhong Jiang and
Jiahong Li

Review
Published 06 Apr 2021

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1. Graphical Abstract
2. Scheme 1: The electron transfer process in EDA complexes.
  
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3. Scheme 2: Synthesis of benzo[b]phosphorus oxide 3 initiated by an EDA complex.
  
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4. Scheme 3: Mechanism of the synthesis of quinoxaline derivative 7.
  
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5. Scheme 4: Synthesis of imidazole derivative 10 initiated by an EDA complex.
  
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6. Scheme 5: Synthesis of sulfamoylation product 12 initiated by an EDA complex.
  
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7. Scheme 6: Mechanism of the synthesis of sulfamoylation product 12.
  
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8. Scheme 7: Synthesis of indole derivative 22 initiated by an EDA complex.
  
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9. Scheme 8: Synthesis of perfluoroalkylated pyrimidines 26 initiated by an EDA complex.
  
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10. Scheme 9: Synthesis of phenanthridine derivative 29 initiated by an EDA complex.
  
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11. Scheme 10: Synthesis of cis-tetrahydroquinoline derivative 32 initiated by an EDA complex.
  
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12. Scheme 11: Mechanism of the synthesis of cis-tetrahydroquinoline derivative 32.
  
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13. Scheme 12: Synthesis of phenanthridine derivative 38 initiated by an EDA complex.
  
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14. Scheme 13: Synthesis of spiropyrroline derivative 40 initiated by an EDA complex.
  
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15. Scheme 14: Synthesis of benzothiazole derivative 43 initiated by an EDA complex.
  
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16. Scheme 15: Synthesis of perfluoroalkyl-s-triazine derivative 45 initiated by an EDA complex.
  
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17. Scheme 16: Synthesis of indoline derivative 47 initiated by an EDA complex.
  
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18. Scheme 17: Mechanism of the synthesis of spirocyclic indoline derivative 47.
  
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19. Scheme 18: Synthesis of cyclobutane product 50 initiated by an EDA complex.
  
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20. Scheme 19: Mechanism of the synthesis of spirocyclic indoline derivative 50.
  
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21. Scheme 20: Synthesis of 1,3-oxazolidine compound 59 initiated by an EDA complex.
  
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22. Scheme 21: Synthesis of trifluoromethylated product 61 initiated by an EDA complex.
  
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23. Scheme 22: Synthesis of indole alkylation product 64 initiated by an EDA complex.
  
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24. Scheme 23: Synthesis of perfluoroalkylation product 67 initiated by an EDA complex.
  
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25. Scheme 24: Synthesis of hydrotrifluoromethylated product 70 initiated by an EDA complex.
  
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26. Scheme 25: Synthesis of β-trifluoromethylated alkyne product 71 initiated by an EDA complex.
  
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27. Scheme 26: Mechanism of the synthesis of 2-phenylthiophene derivative 74.
  
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28. Scheme 27: Synthesis of allylated product 80 initiated by an EDA complex.
  
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29. Scheme 28: Synthesis of trifluoromethyl-substituted alkynyl product 84 initiated by an EDA complex.
  
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30. Scheme 29: Synthesis of dearomatized fluoroalkylation product 86 initiated by an EDA complex.
  
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31. Scheme 30: Mechanism of the synthesis of dearomatized fluoroalkylation product 86.
  
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32. Scheme 31: Synthesis of C(sp³)–H allylation product 91 initiated by an EDA complex.
  
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33. Scheme 32: Synthesis of perfluoroalkylation product 93 initiated by an EDA complex.
  
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34. Scheme 33: Synthesis of spirocyclic indolene derivative 95 initiated by an EDA complex.
  
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35. Scheme 34: Synthesis of perfluoroalkylation product 97 initiated by an EDA complex.
  
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36. Scheme 35: Synthesis of alkylated indole derivative 100 initiated by an EDA complex.
  
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37. Scheme 36: Mechanism of the synthesis of alkylated indole derivative 100.
  
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38. Scheme 37: Synthesis of arylated oxidized indole derivative 108 initiated by an EDA complex.
  
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39. Scheme 38: Synthesis of 4-ketoaldehyde derivative 111 initiated by an EDA complex.
  
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40. Scheme 39: Mechanism of the synthesis of 4-ketoaldehyde derivative 111.
  
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41. Scheme 40: Synthesis of perfluoroalkylated olefin 118 initiated by an EDA complex.
  
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42. Scheme 41: Synthesis of alkylation product 121 initiated by an EDA complex.
  
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43. Scheme 42: Synthesis of acylation product 123 initiated by an EDA complex.
  
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44. Scheme 43: Mechanism of the synthesis of acylation product 123.
  
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45. Scheme 44: Synthesis of trifluoromethylation product 126 initiated by an EDA complex.
  
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46. Scheme 45: Synthesis of unnatural α-amino acid 129 initiated by an EDA complex.
  
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47. Scheme 46: Synthesis of thioether derivative 132 initiated by an EDA complex.
  
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48. Scheme 47: Synthesis of S-aryl dithiocarbamate product 135 initiated by an EDA complex.
  
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49. Scheme 48: Mechanism of the synthesis of S-aryl dithiocarbamate product 135.
  
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50. Scheme 49: Synthesis of thioether product 141 initiated by an EDA complex.
  
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51. Scheme 50: Mechanism of the synthesis of borate product 144.
  
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52. Scheme 51: Synthesis of boronation product 148 initiated by an EDA complex.
  
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53. Scheme 52: Synthesis of boration product 151 initiated by an EDA complex.
  
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54. Scheme 53: Synthesis of boronic acid ester derivative 154 initiated by an EDA complex.
  
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55. Scheme 54: Synthesis of β-azide product 157 initiated by an EDA complex.
  
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56. Scheme 55: Decarboxylation reaction initiated by an EDA complex.
  
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57. Scheme 56: Synthesis of amidated product 162 initiated by an EDA complex.
  
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58. Scheme 57: Synthesis of diethyl phenylphosphonate 165 initiated by an EDA complex.
  
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59. Scheme 58: Mechanism of the synthesis of diethyl phenylphosphonate derivative 165.
  
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60. Scheme 59: Synthesis of (Z)-2-iodovinyl phenyl ether 168 initiated by an EDA complex.
  
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61. Scheme 60: Mechanism of the synthesis of (Z)-2-iodovinyl phenyl ether derivative 168.
  
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62. Scheme 61: Dehalogenation reaction initiated by an EDA complex.
  
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Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

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Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

Soumyaranjan Pati,
Renata G. Almeida,
Eufrânio N. da Silva Júnior and
Irishi N. N. Namboothiri

Letter
Published 31 Mar 2021

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1. Graphical Abstract
2. Scheme 1: Synthesis, functionalization and applications of triazoles.
  
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3. Scheme 2: The reaction was performed using 0.2 mmol N-tosyl-1,2,3-triazole 1 and 0.2 mmol of cyclohexyl-1,3-d...
  
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4. Scheme 3: Control experiments.
  
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5. Scheme 4: Mechanistic proposal for the formation of β-triazolylenones.
  
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6. Figure 1: Nucleophilic addition to 5- and 6-membered cyclic tosyloxyenones.
  
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Beilstein J. Org. Chem. 2021, 17, 762–770, doi:10.3762/bjoc.17.66

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DNA with zwitterionic and negatively charged phosphate modifications: Formation of DNA triplexes, duplexes and cell uptake studies

Yongdong Su,
Maitsetseg Bayarjargal,
Tracy K. Hale and
Vyacheslav V. Filichev

Full Research Paper
Published 29 Mar 2021

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1. Graphical Abstract
2. Figure 1: Illustration of H-bonding in a DNA duplex and a parallel triplex. A) Depiction of Watson–Crick base...
  
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3. Scheme 1: The synthesis of ONs with Ts and N+ modification using the Staudinger reaction during the solid-pha...
  
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4. Figure 2: Percentage of intact ONs after 120 min. A) N+ONs; B) Ts-ONs. Percentage of intact ONs was determine...
  
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5. Figure 3: Representative images of mouse NIH 3T3 fibroblasts incubated with either (A–C) no oligo or 20 µM of...
  
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6. Figure 4: Representative confocal microscopy section showing the FAM vesicles inside the cell. Mouse NIH 3T3 ...
  
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Beilstein J. Org. Chem. 2021, 17, 749–761, doi:10.3762/bjoc.17.65

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Simulating the enzymes of ganglioside biosynthesis with Glycologue

Andrew G. McDonald and
Gavin P. Davey

Full Research Paper
Published 23 Mar 2021

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1. Graphical Abstract
2. Figure 1: Chemical structure of ganglioside GM1a (a β-ᴅ-galactosyl-(1→3)-N-acetyl-β-ᴅ-galactosaminyl-(1→4)-[α-...
  
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3. Figure 2: Construction of the Svennerholm name GP1cα from its Glycologue structure identifier. At each step o...
  
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4. Figure 3: Ganglioside carbohydrates predicted by the model. All structures are linked to ceramide at the base...
  
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5. Figure 4: Ganglioside biosynthetic reaction network predicted by the Glycologue enzyme simulator. Starting fr...
  
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6. Figure 5: Predicted effects on the pathways of ganglioside biosynthesis when individual enzyme activities are...
  
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Beilstein J. Org. Chem. 2021, 17, 739–748, doi:10.3762/bjoc.17.64

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Organo-fluorine chemistry V

David O’Hagan

Editorial
Published 17 Mar 2021

Beilstein J. Org. Chem. 2021, 17, 737–738, doi:10.3762/bjoc.17.63

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Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

Takashi Nishiyama,
Erina Hamada,
Daishi Ishii,
Yuuto Kihara,
Nanase Choshi,
Natsumi Nakanishi,
Mari Murakami,
Kimiko Taninaka,
Noriyuki Hatae and
Tominari Choshi

Full Research Paper
Published 16 Mar 2021

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1. Graphical Abstract
2. Figure 1: Natural products possessing the pyrrolo[2,3-c]quinoline skeleton.
  
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3. Scheme 1: Total synthesis of marinoquinolines and the failure of the introduction of a tetrahydroquinoline mo...
  
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4. Scheme 2: Retrosynthetic analysis of the pyrrolo[2,3-c]quinoline ring construction.
  
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5. Scheme 3: Synthesis of N-substituted 4-aminopyrrolo[3,2-c]quinoline 18.
  
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6. Scheme 4: Synthesis of the tetrahydroquinoline moiety through cycloamination.
  
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7. Scheme 5: Synthesis of trigonoine B (1).
  
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