A p-toluenesulfinic acid-catalyzed three-component Ugi-type reaction and its application for the synthesis of α-amino amides and amidines

Biswajit Saha, Brendan Frett, Yuanxiang Wang, Hong Yu Li

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

A mild, cost-effective, and simple three-component Ugi-type reaction using p-toluenesulfinic acid (pTSIA) as the acid catalyst has been developed to synthesize α-amino amides and α-amino amidines. Employing 1 equiv of amine used in the reaction generated α-amino amides exclusively, while 2 equiv of amines, especially with more nucleophilic aniline such as p-anisidine, yielded the α-amino amidines as the major product. This methodology would be suitable for the synthesis of natural or unnatural amino acids and drug-like amidine analogues.

Original languageEnglish (US)
Pages (from-to)2340-2343
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number19
DOIs
StatePublished - May 8 2013

Keywords

  • Amide
  • Amidine
  • MCR
  • Three-component Ugi reaction
  • p-Toluenesulfinic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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