Synthesis of benzamide-benzothiazole conjugates via palladium-catalysed aminocarbonylation (hydrazinocarbonylation)

Gergely, Máté and Kollár, László (2019) Synthesis of benzamide-benzothiazole conjugates via palladium-catalysed aminocarbonylation (hydrazinocarbonylation). TETRAHEDRON, 75 (13). pp. 2027-2036. ISSN 0040-4020

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Abstract

The palladium-catalysed aminocarbonylation of iodoarenes was investigated using 2-amino- and 2-hydrazinobenzothiazole as N-nucleophile. The reaction proved to be highly chemoselective in all cases: carboxamides and the corresponding carbohydrazides, obtained by the acylation at the nitrogen adjacent to the C-2 of the benzothiazole moiety, were obtained exclusively and isolated in moderate to high yields. Systematic investigation of the reaction conditions revealed that the reaction requires relatively high temperature (higher than 70 C). The effect of the carbon monoxide pressure is different in the synthesis of the two types of products: while the carboxamide formation is favoured, the carbohydrazide formation is lowered by the increasing CO pressure.

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