(Hex-2-en-ylidene)-N-Substituted Hydrazinecarbothioamides and 2,3-Dichloro-1,4-naphthoquinone: Nucleophilic Substitution Reactions and Synthesis of Naphtho[2,3-f][1,3,4]thiadiazepines and Naphtho[2,3-d]thiazoles

Abstract

The coupling reaction between N-substituted (E)-hex-2-en-ylidene hydrazinecarbothioamides and 2,3-dichloro-1,4-naphthoquinone affords substituted amino-5-pentenyl-naphtho[2,3-f]-1,3,4-thiadiazepine-6,11-diones and 2-(substituted amino)naphtho[2,3-d]thiazole-4,9-diones. These conversions can be rationalized by proposing a nucleophilic addition to C2 and C3 of dichloro-1,4-naphthoquinone. The structure of one of the products was confirmed by single-crystal X-ray analysis.

Key words

naphthoquinones - naphthothiadiazepines - naphthothiazoles - nucleophilic substitution

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