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Paper | Regular issue | Vol 100, No. 11, 2020, pp.1859-1882
Published online, 25th August, 2020
DOI: 10.3987/COM-20-14333
Synthesis and Reactivity of Dimethoxy Activated Benzothiazoles

Mahiuddin Alamgir, Hao Jiang, Mohan Bhadbhade, Naresh Kumar, and David StC. Black*

*School of Chemistry, The University of New South Wales, Sydney 2052, Australia


A range of 2-substituted-5,7-dimethoxybenzothiazoles and 2-substituted-4,6-dimethoxybenzothiazoles have been synthesized by oxidative cyclization of the corresponding thioamides. These activated benzothiazoles display nucleophilic reactivity at C4 and C7 respectively and undergo formylation, acetylation and related reactions. Some 5,7-dimethoxybenzothiazoles with functionalization in a 2-aryl substituent are also reported as potential precursors for so far unsuccessful formation of macrocycles containing two benzothiazoles and two benzimidazoles.