The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

Tilman Lechel, Roopender Kumar, Mrinal K. Bera, Reinhold Zimmer and Hans-Ulrich Reissig
Beilstein J. Org. Chem. 2019, 15, 655–678. https://doi.org/10.3762/bjoc.15.61

Cite the Following Article

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives
Tilman Lechel, Roopender Kumar, Mrinal K. Bera, Reinhold Zimmer and Hans-Ulrich Reissig
Beilstein J. Org. Chem. 2019, 15, 655–678. https://doi.org/10.3762/bjoc.15.61

How to Cite

Lechel, T.; Kumar, R.; Bera, M. K.; Zimmer, R.; Reissig, H.-U. Beilstein J. Org. Chem. 2019, 15, 655–678. doi:10.3762/bjoc.15.61

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 204.0 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Vchislo, N. V.; Verochkina, E. A.; Fedoseeva, V. G. Synthesis of alkenyl- and alkynyloxazoles and –oxazolines using tosylmethyl isocyanide as a key building block (microreview). Chemistry of Heterocyclic Compounds 2023, 59, 537–539. doi:10.1007/s10593-023-03229-4
  • Hussain, R.; Rehman, W.; Rahim, F.; Mahmoud, A. M.; Alanazi, M. M.; Khan, S.; Rasheed, L.; Khan, I. Synthetic transformation of 6-Fluoroimidazo[1,2-a]Pyridine-3-carbaldehyde into 6-Fluoroimidazo[1,2-a]Pyridine-Oxazole Derivatives: In vitro urease inhibition and in silico study. Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society 2023, 31, 101667. doi:10.1016/j.jsps.2023.05.026
  • Vchislo, N. V.; Fedoseeva, V. G.; Verochkina, E. A. The Reactions of p-Tosylmethyl Isocyanide with Aldehydes in the Synthesis of Heterocyclic Compounds: A Review. Mini-Reviews in Organic Chemistry 2023, 20, 372–393. doi:10.2174/1570193x19999220523113243
  • Kurzawa, T.; Zimmer, R.; Würthwein, E.-U.; Reissig, H.-U. The Boekelheide Rearrangement of Pyrimidine N-oxides as a Case Study of Closed or Open Shell Reactions - Experimental and Computational Evidence for the Participation of Radical Intermediates. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202204015. doi:10.1002/chem.202204015
  • Murray, B. A. doi:10.1002/9781119608288.ch1
  • Reissig, H.-U.; Alam Chowdhury, M. Asymmetric Synthesis of the Unnatural Enantiomer of Codonopsinine and a Stereoisomer via Alkoxyallenes. HETEROCYCLES 2023, 106, 858. doi:10.3987/com-23-14837
  • Mazibuko, M.; Jeena, V. Synthesis of 2,4,5-Trisubstituted Oxazoles from Copper-Mediated Benzylic sp3 C-H Aerobic Oxidative Annulation of Ketones and Amines via a Cascade Reaction. The Journal of organic chemistry 2022, 88, 1227–1234. doi:10.1021/acs.joc.2c02148
  • Hapke, M. Comprehensive Heterocyclic Chemistry IV - Pyridines and Benzo Derivatives: Synthesis. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 150–216. doi:10.1016/b978-0-12-818655-8.00108-6
  • Cao, T.; Martini, M. L.; Park, K.-S.; Kaniskan, H. Ü.; Jin, J. Comprehensive Heterocyclic Chemistry IV - Pyrimidines and Their Benzo Derivatives. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 86–228. doi:10.1016/b978-0-12-818655-8.00041-x
  • Belen'kii, L. I.; Gazieva, G. A.; Evdokimenkova, Y. B.; Soboleva, N. O. The literature of heterocyclic chemistry, Part XIX, 2019. Advances in Heterocyclic Chemistry; Elsevier, 2022; pp 225–295. doi:10.1016/bs.aihch.2021.09.002
  • Vidal, M.; Rodríguez‐Aguilar, J.; Aburto, I.; Aliaga, C.; Domínguez, M. Reactivity of 4‐pyrimidyl Sulfonic Esters in Suzuki‐Miyaura Cross‐Coupling Reactions in Water Under Microwave Irradiation. ChemistrySelect 2021, 6, 12858–12861. doi:10.1002/slct.202103280
  • Brennecke, B.; Micó, A. C.; Selter, L.; Accorsi, M.; Zimmer, R.; Reissig, H.-U. A Proline and 4-Hydroxyproline Based Approach to Enantiopure Pyrrolidin-2-yl-Substituted Pyridine and Pyrimidine Derivatives. European Journal of Organic Chemistry 2021, 2021, 4750–4761. doi:10.1002/ejoc.202100887
  • Rinderspacher, K. A. Six-membered ring systems: diazines and benzo derivatives. Progress in Heterocyclic Chemistry; Elsevier, 2021; pp 431–466. doi:10.1016/b978-0-323-89812-6.00013-4
  • Ashraf, M. A.; Liu, Z.; Li, C.; Zhang, D. Recent advances in catalytic silylation of hydroxyl‐bearing compounds: A green technique for protection of alcohols using Si–O bond formations. Applied Organometallic Chemistry 2020, 35. doi:10.1002/aoc.6131
  • Chen, L.; Zhang, L.; Tian, Y.; Li, J.; Liu, Y. Copper/Iodine-Cocatalyzed C-C Cleavage of 1,3-Dicarbonyl Compounds Toward 1,2-Dicarbonyl Compounds. European Journal of Organic Chemistry 2020, 2020, 5523–5526. doi:10.1002/ejoc.202000795
  • Zheng, X.; Liu, W.; Zhang, D. Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis. Molecules (Basel, Switzerland) 2020, 25, 1594. doi:10.3390/molecules25071594
  • Lu, Y.; Luo, M.-J.; Hu, M.; Li, Y.; Li, J.-H. Dimethyl Sulfoxide as an Oxygen Atom Source Enabled Tandem Conversion of 2‐Alkynyl Carbonyls to 1,2‐Dicarbonyls. Advanced Synthesis & Catalysis 2020, 362, 1846–1850. doi:10.1002/adsc.202000066
  • Kumar, R.; Bera, M. K.; Zimmer, R.; Lentz, D.; Reissig, H.-U.; Würthwein, E.-U. Alkoxyallene-Based LANCA Three-Component Synthesis of 1,2-Diketones, Quinoxalines, and Unique Isoindenone Dimers and a Computational Study of the Isoindenone Dimerization. European Journal of Organic Chemistry 2020, 2020, 1753–1763. doi:10.1002/ejoc.202000116
  • Reissig, V. M. S. a. H.-U. Alkoxyallenes as Starting Materials for the Syntheses of Natural Products. Current Organic Chemistry 2020, 23, 2976–3003. doi:10.2174/1385272824666191218115731
Other Beilstein-Institut Open Science Activities