A new one-pot synthesis of pseudopeptide connected to sulfonamide: Via the tandem N -sulfonylation/Ugi reactions

In this study, an efficient one-pot reaction is reported for the synthesis of a new class of pseudopeptide connected to sulfonamide via a tandem N-sulfonylation/Ugi four-component reaction (Ugi-4CR) strategy under mild conditions in high yields. This five-component reaction strategy is carried out by readily available starting materials, sulfonyl chlorides, glycines, benzylamines, benzaldehydes, and isocyanides, in ethanol/water at room temperature. The generation of carboxylic acid that is a key component in Ugi-4CR could be accomplished by performing the N-sulfonylation reaction, and it could be used in the next step without further purification. The as-synthesized compounds that are constructed from pseudopeptide connected to a sulfonamide scaffold have the potential to be used in designing modern drugs with the highly desirable feature. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Authors
Nazeri M.T.1 , Beygzade Nowee A. , Shaabani A. 1, 2
Publisher
Royal Society of Chemistry
Number of issue
7
Language
English
Pages
3479-3484
Status
Published
Volume
45
Year
2021
Organizations
  • 1 Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, 19396-4716, Iran
  • 2 Peoples' Friendship University of Russia, RUDN University, 6, Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
Keywords
Amino acids; Chlorine compounds; Scaffolds; Desirable features; Ethanol/water; One-pot reaction; One-pot synthesis; Pseudo-peptide; Reaction strategies; Sulfonyl chlorides; Sulfonylation reactions; Sulfur compounds
Date of creation
20.04.2021
Date of change
20.04.2021
Short link
https://repository.rudn.ru/en/records/article/record/72111/
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