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

21 Citations (Scopus)

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

Fingerprint

Amidines
Amides
Amines
Amino Acids
Costs and Cost Analysis
Catalysts
Acids
Pharmaceutical Preparations
4-toluenesulfinic acid
Costs

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A p-toluenesulfinic acid-catalyzed three-component Ugi-type reaction and its application for the synthesis of α-amino amides and amidines. / Saha, Biswajit; Frett, Brendan; Wang, Yuanxiang; Li, Hong Yu.

In: Tetrahedron Letters, Vol. 54, No. 19, 08.05.2013, p. 2340-2343.

Research output: Contribution to journalArticle

@article{daf0b1631b99464cb780d182604b0a5a,
title = "A p-toluenesulfinic acid-catalyzed three-component Ugi-type reaction and its application for the synthesis of α-amino amides and amidines",
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.",
keywords = "Amide, Amidine, MCR, p-Toluenesulfinic acid, Three-component Ugi reaction",
author = "Biswajit Saha and Brendan Frett and Yuanxiang Wang and Li, {Hong Yu}",
year = "2013",
month = "5",
day = "8",
doi = "10.1016/j.tetlet.2013.02.055",
language = "English (US)",
volume = "54",
pages = "2340--2343",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "19",

}

TY - JOUR

T1 - A p-toluenesulfinic acid-catalyzed three-component Ugi-type reaction and its application for the synthesis of α-amino amides and amidines

AU - Saha, Biswajit

AU - Frett, Brendan

AU - Wang, Yuanxiang

AU - Li, Hong Yu

PY - 2013/5/8

Y1 - 2013/5/8

N2 - 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.

AB - 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.

KW - Amide

KW - Amidine

KW - MCR

KW - p-Toluenesulfinic acid

KW - Three-component Ugi reaction

UR - http://www.scopus.com/inward/record.url?scp=84875952700&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84875952700&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.02.055

DO - 10.1016/j.tetlet.2013.02.055

M3 - Article

AN - SCOPUS:84875952700

VL - 54

SP - 2340

EP - 2343

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 19

ER -