Synthetic exploitation of halogenated alkenes containing EWG: benzotriazole-mediated synthesis of benzoazetines and thermal transformations

Abstract

The series of stable benzoazetine derivatives (5a–d) based on nitrovinyl moieties have been synthesized via transamination of bisbenzotriazolyl derivatives (2a–c). Four new heptatomic aromatic cycloheterocumulenes (azacyclohepta-1,2,4,6-tetraene) occurring at the stage of the film-forming process by TVE have been obtained by rearrangement of benzoazetines. The highly strained products were characterized by IR spectroscopy.