An efficient, one-pot, regioselective synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles under solvent-free conditions. (2nd January 2022)

• Record Type: Journal Article
• Authors: Aggarwal, Ranjana; Hooda, Mona; Jain, Naman; Sanz, Dionisia; Claramunt, Rosa M.; Twamley, Brendan; Rozas, Isabel
• Is Part Of: Journal of sulfur chemistry. Volume 43:Number 1(2022)
• Page Start: 12
• Page End: 21
• Publication Date: 2022-01-02
• Subjects: Unsymmetrical 1, 3-diketones -- N-bromosuccinimide -- thioamides -- 2-aryl/hetaryl-4-methyl-5-acylthiazoles -- multinuclear 2D NMR; Sulfur -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.72305
• DOI: 10.1080/17415993.2021.1975119
• Languages: English
• ISSNs: 1741-5993

Abstract

Abstract : In this article, we present an efficient, one-pot regioselective approach towards the synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles obtained during the reaction of α-bromo-1, 3-diketones generated in situ by triturating unsymmetrical 1, 3-diketones with N -bromosuccinimide, with various thioamides under solvent-free conditions. This environmentally benign protocol showed large functional group tolerance, resulted in the exclusive formation of a single isomer, out of the two possible regioisomers in admirable yields. The structure of the isomeric thiazole was assigned unambiguously on the basis of multinuclear NMR [( 1 H- 13 C) HMBC, ( 1 H- 13 C) HMQC, ( 1 H- 15 N) HMBC] and X-ray crystallographic studies. The entire protocol is ecologically desirable as it employs no organic solvent. GRAPHICAL ABSTRACT: UF0001