Synthesis of Nitrobenzazoles

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Abstract

A great deal of information on the methods of synthesis of nitrated benzo analogs – indazoles, benzimidazoles, benzoxazoles, benzisoxazoles, benzoxadiazoles, benzothiazoles, benzoisothiazoles, benzothiadiazoles, benzotriazoles, benzoselenazoles, benzoselenadiazoles – is systematized, summarized, and critically discussed. Major attention is paid to electrophilic nitration, a much used and convenient method for the preparation of nitrobenzazoles. The nitration of benzazoles is a complex process in which the experimental conditions can modify the product orientation. The existence of an annelated benzene ring in the benzazole molecule influences much of its ability for electrophilic substitution – all benzazoles are more easily nitrated than their five-membered analogs, and the nitro group is generally introduced into the arylene fragment of the molecule. Vicarious nucleophilic C-amination of benzazoles, practically, the single method of direct introduction of the amino group into nitro compounds is presented.