Citation: Liuwenlin Han, Changbin Guo. Progress in Passerini Multicomponent Reactions[J]. Chemistry, ;2021, 84(4): 346-352. shu

Progress in Passerini Multicomponent Reactions

Liuwenlin Han ,
Changbin Guo ^,

Department of Chemistry, Capital Normal University, Beijing, 100048

Corresponding author: Changbin Guo, guocb@cnu.edu.cn
Received Date: 15 September 2020
Accepted Date: 12 October 2020

The multi-component reaction is an important type of organic chemical reactions, which has the characteristics of simple operation and high atom economy. The classic Passerini reaction is a multi-component reaction which use an isocyanide, an aldehyde (or a ketone) and a carboxylic acid to synthesize an α-acyloxycarboxamide in one pot. As a class of important organic intermediates, α-acyloxycarboxamides have a wide range of uses, and can be used to further synthesize many important complex organic molecules such as drugs, natural products and functional materials. This article summarizes the new progress of Passerini reactions in the past 5 years from the perspective of reaction substrates, tandem reactions and related applications.
- Multi-component reaction,
- Passerini reaction,
- Isocyanide,
- Aldehyde,
- Carboxylic acid
1. [1]
2. [2]
  Varadi A, Palmer T C, Dardashti R N, et al. Molecules, 2016, 21(1): 19~41.
3. [3]
  Wang Q, Wang D X, Wang M X, et al. Acc. Chem. Res., 2018, 51: 1290~1300.
4. [4]
  Domling A, Ugi I. Angew. Chem. Int. Ed., 2000, 39(18): 3168~3210.
5. [5]
  Maeda S, Komagawa S, Uchiyama M, et al. Angew. Chem. Int. Ed., 2011, 50: 644~649.
6. [6]
  Ramozzi R, Morokuma K. J. Org. Chem., 2015, 80: 5652~5657.
7. [7]
  van der Heijden G, Jong J A W, Ruijter E, et al. Org. Lett., 2016, 18: 984~987.
8. [8]
  Shen Y Y, Huang B, Zeng L W, et al. Org. Lett., 2017, 19: 4616~4619.
9. [9]
  Wu D, Li J, Wang W. Eur. J. Org. Chem., 2018, 2018(23): 3022~3030.
10. [10]
  Soeta T, Matsuzaki S, Ukaji Y. J. Org. Chem., 2015, 80: 3688~3694.
11. [11]
  Chandgude A L, Domling A. Org. Lett., 2016, 18: 6396~6399.
12. [12]
  Saya J M, Berabez R, Broersen P, et al. Org. Lett., 2018, 20: 3988~3991.
13. [13]
  Neo A G, Marcos C F. Org. Lett. 2018, 20: 3875~3878.
14. [14]
  Onwukamike K N, Grelier S, Grau E, et al. RSC Adv., 2018, 8: 31490~31495.
15. [15]
  Jessop P G, Heldebrant D J, Li X, et al. Nature, 2005, 436(7054): 1102.
16. [16]
  Wang L, Ren Z L, Ding M W. J. Org. Chem., 2015, 80: 641~646.
17. [17]
  Liu M G, Liu N, Xu W H, et al. Tetrahedron, 2019, 75: 2748~2754.
18. [18]
  Wang L, Guan Z R, Ding M W. Org. Biomol. Chem., 2016, 14: 2413~2420.
19. [19]
  Liu N, Chao F, Liu M G, et al. J. Org. Chem., 2019, 84: 2366~2371.
20. [20]
  Kaur G, Vadekeetil A, Harjai K, et al. Tetrahed. Lett., 2015, 56: 4445~4450.
21. [21]
  Hasan M, Zaman M, Peshkov A A, et al. Eur. J. Org. Chem., 2020, 2020(23): 3378~3389.
22. [22]
  van der Heijden G, Kraakman J, Biemolt J, et al. Org. Biomol. Chem., 2016, 14: 9716~9719.
23. [23]
  Adib M, Sheikhi E, Azimzadeh M. Tetrahed. Lett., 2015, 56: 1933~1936.
24. [24]
  Feng Q X, Mu Z Y, Yao G, et al. Synlett., 2020, 31(10): 1003~1006.
25. [25]
  Kutovaya I V, Nenajdenko V G. Russ. J. Org. Chem., 2020, 56(4): 559~568.
26. [26]
  dos Santosa D A, da Silvaa A R, Ellena J, et al. Synthesis, 2020, 52(7): 1076~1086.
27. [27]
  Gao Q, Hao W J, Liu F, et al. Chem. Commun., 2016, 52(5): 900~903.
28. [28]
  Ponra S, Nyadanu A, El Kaim L, et al. Org. Lett., 2016, 18: 4060~4063.
29. [29]
  Cioc R C, Estevez V, van der Niet D J, et al. Eur. J. Org. Chem., 2017, 2017(9): 1262~1271.
30. [30]
  Narboni N, EI Kaim L. Eur. J. Org. Chem., 2017, 2017(29): 4242~4246.
31. [31]
32. [32]
  Serafini M, Griglio A, Oberto E, et al. Tetrahed. Lett., 2017, 58: 4786~4789.
33. [33]
  Wang R, Liu Z Q. Tetrahed. Lett., 2015, 56: 7028~7033.
34. [34]
  Morejon M C, Laub A, Kaluderovic G N, et al. Org. Biomol. Chem., 2017, 15: 3628~3637.
35. [35]
  Vlahovicek-Kahlina K, Vazdar M, Jakas A, et al. J. Org. Chem., 2018, 83: 13146~13156.
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