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Thiopegan Derivatives. Part XXV. Synthesis of 9,10-Thiopegan Derivatives Contaiaing a Saturated Thiazole Moiety

Authors: Singh, Harjit; K. S. Bhandari; K. S. Narang;

Thiopegan Derivatives. Part XXV. Synthesis of 9,10-Thiopegan Derivatives Contaiaing a Saturated Thiazole Moiety

Abstract

Condensation of N-allylanthranilic acid hydrochloride with potassium thiocyanate furnishes 1-allyl-2- mercapto-4-keto-tetrahydroquinazoline (V). Cyclisation of (V) with HCl provides 2-methyl-9,10-thiopega-10- en-4-one (VII). Bromination of (V) results in its cyclisation to 2-bromomethyl-9,10-thiopega-19-en-4-one, which has been dehydrobrominated to 2-methylene-9,10-thiopega-10-en-4-one (XI). This compound has been converted by bromination and dehydrobromination to 2-bromomethyl-9,10-thiopega-2,10-dien-4-one (XIV). The latter has been condensed with piperidine and with morpholine. The products (XI and XIV) on treat­ment with H2SO4, zinc, and acetic acid furnish 2-methyl-9, 10-thiopega-2,10-mean-4-one (XV). The structures of all these compounds have been confirmed by unambiguous synthesis of (XV). Some of these compounds show weak antibacterial activity.

Keywords

Thiopegan Derivatives, Biological screening, Alkaline solution

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