Pyrolysis of 1-amino-8-azidonaphthalene derivatives. New routes to oxazoles, perimidines, and benz[cd]indazoles

Abstract

Brief heating of monoacyl and aroyl derivatives of 1-amino-8-azidonaphthalene gives 9-amino-2-substituted naphth[1,2-d]oxazoles and 2-substituted perimidines, whilst the N-acetyl-N-methyl and N,N-diacetyl derivatives give 1,2-disubstituted 1,2-dihydrobenz[cd]indazoles: mechanisms are suggested for these novel transformations.