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4. Synthesis and Reactivity of 2-(Furan-2-yl)benzo[1,2-d:4,3-d′]bis[1,3]thiazole.

Author

Aleksandrov, A. A., Elchaninov, M. M., Tishina, D. A., Tarakanova, Yu. E., and Shmanovsky, M. L.

Subjects
ELECTROPHILIC substitution reactions, THIOAMIDES, FORMYLATION, ACYLATION, NITRATION
Abstract

Acylation of 1,3-benzothiazol-6-amine with furan-2-carbonyl chloride in propan-2-ol gave N-(1,3-benzothiazol-6-yl)furan-2-carboxamide which was converted to the corresponding thioamide by treat-ment with excess P2S5 in anhydrous toluene. The subsequent oxidation with potassium hexacyanoferrate(III) in alkaline medium afforded 2-(furan-2-yl)benzo[1,2-d:4,3-d′]bis[1,3]thiazole which was subjected to electrophilic substitution reactions (bromination, nitration, hydroxymethylation, formylation, acylation). The substituent entered exclusively into the 5-position of the furan ring. [ABSTRACT FROM AUTHOR]

Published
2021
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