2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization

ABSTRACT: Reactions of 2-amino-1,3-benzothiazole with aliphatic, aromatic and heteroaromatic α-iodoketones in the absence of bases or catalysts have been studied. The reaction proceeds by N-alkylation of the endocyclic nitrogen atom followed by intramolecular dehydrative cyclization. The regioselectivity is explained and the mechanism of the reaction is proposed. A number of new linear and cyclic iodide and triiodide benzothiazolium salts have been obtained and their structure proved by NMR and UV spectroscopy.

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PROVIDER: S-EPMC10004639 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature