(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

作者：Hassan Alaa A^*; Mohamed Nasr K; Makhlouf Maysa M; Braese Stefan; Nieger Martin; Hopf Henning

来源：Synthesis (Germany), 2016, 48(18): 3134-3140.

DOI：10.1055/s-0035-1562133

• naphthoquinones
• naphthothiadiazepines
• naphthothiazoles
• nucleophilic substitution

The coupling reaction between N-substituted (E)-hex-2-enylidene 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 Xray analysis.

• 出版日期2016-9