Investigation of Interaction of Benzoquinones and Naphthoquinones with Substituted Hydrazides

摘要

Nucleophilic attack by substituted hydrazides on C-2, C-3 of 2,3,5,6-tetrachloro-14-benzoquinone and 2,3-dichloro-1,4-naphthoquinone initiates the formation of benzo[e][1,3,4]oxadiazine and benzo- as well as naphthoxadiazepine derivatives. On the other hand, substituted hydrazides attack 1,4-naphthoquinone-2,3-dicarbonitrile to form benzo[f]indazole-4,9-dione derivatives. A rationale for the conversions observed is presented.