Efficient approach to thiazolidinones via a one-pot three-component reaction involving 2-amino-1-phenylethanone hydrochloride, aldehyde and mercaptoacetic acid

doi:10.1016/S1872-2067(16)62536-6

Abstract

Abstract:

A highly efficient three-component reaction has been developed for the synthesis of thiazolidinones involving the reaction of 2-amino-1-phenylethanone hydrochloride with an aromatic aldehyde and mercaptoacetic acid in the presence of diisopropylethylamine in a single pot. Critically, this reaction exhibited excellent chemoselectivity, with the nitrogen atom of the 2-amino-1-phenylethanone component reacting selectively with the aromatic aldehyde to give the corresponding Schiff base. Nucleophilic attack at the carbon of the Schiff base by the sulfur atom of mercaptoacetic, followed by a cyclocondensation reaction between the nitrogen and the carboxylic acid moiety afforded the desired thiazolidinones, which were fully characterized by spectroscopic techniques.

Key words: Tandem reaction, Thiazolidinones, Heterocycles, N,N-diisopropylethylamine, Cyclization

Asha Vasantrao Chate, Akash Gitaram Tathe, Prajyot Jayadev Nagtilak, Sunil M. Sangle, Charansingh H. Gill. Efficient approach to thiazolidinones via a one-pot three-component reaction involving 2-amino-1-phenylethanone hydrochloride, aldehyde and mercaptoacetic acid[J]. Chinese Journal of Catalysis, 2016, 37(11): 1997-2002.

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