Brønsted acid promoted addition-cyclization and C-C bond cleavage: a convenient synthesis of 2-amino-5-aroylmethylthiazoles derivatives

A Brønsted acid promoted C-C bond cleavage method for the synthesis of novel 2-amino-5-aroylmethylthiazole derivatives has been directly developed from 1,4-enediones and thioureas through self-sequenced thio-Michael-addition, intramolecular selective cyclization, dehydration/aromatization, and C-C b...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-12, Vol.12 (46), p.9466-9470
Main Authors: Ni, Fan, Yang, Yan, Shu, Wen-Ming, Ma, Jun-Rui, Wu, An-Xin
Format: Article
Language:English
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Summary:A Brønsted acid promoted C-C bond cleavage method for the synthesis of novel 2-amino-5-aroylmethylthiazole derivatives has been directly developed from 1,4-enediones and thioureas through self-sequenced thio-Michael-addition, intramolecular selective cyclization, dehydration/aromatization, and C-C bond cleavage reactions. It is noteworthy that this reaction has significant advantages in simple reagents, under environmentally benign conditions and with excellent yields. This highly efficient method is also a highly attractive alternative for the preparation of PLTP, CETP inhibitors and novel biheterocycles.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01519c