Reaction of unsymmetrical α-bromo-1,3-diketones with N-substituted thioureas: regioselective access to 2-(N-arylamino)-5-acyl-4-methylthiazoles and/or rearranged 2-(N-acylimino)-3-N-aryl-4-methylthiazoles.

ABSTRACT: The present study reports some fascinating results of Hantzsch's [3 + 2] cyclic condensation of α-bromo-1,3-diketones, a tri-electrophilic synthon generated in situ by bromination of 1,3-diketones using the mild brominating reagent NBS with trinucleophilic N-substituted thioureas. Interestingly, out of a total of 20 combinations, 10 resulted in the exclusive formation of the desired 2-(N-arylamino)-5-acyl-4-methylthiazoles regioselectively, seven led to the formation of unexpected 2-(N-acylimino)-3-N-aryl-4-methylthiazoles through an interesting C-N acyl migration, and three furnished a mixture consisting of both products. The regioselectivity pattern of the two products may be attributed to a greater electrophilicity of the carbonyl carbon of the acetyl

SUBMITTER: Aggarwal R 

PROVIDER: S-EPMC11544347 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature