Dibenz[b,f][1,4]oxazepine: homogeneous and heterogeneous reactions with sodium dichloroisocyanurate (FiClor)

Abstract

Dibenz[b,f][1,4]oxazepine (1) reacts with sodium dichloroisocyanurate (FiClor) under homogeneous conditions in aqueous ethanol to afford salicylaldehyde as the preponderant primary product, together with smaller amounts of N-formylphenoxazine and 2-(2-hydroxyphenyl)benzoxazole. All the products result from oxidation of the azomethine group in (1). Dibenz[b,f][1,4]oxazepine reacts with FiClor under heterogeneous conditions in chloroform–water mixtures to give preponderantly the nuclear chlorinated derivatives 7-chloro-, 9-chloro-, and 7,9-dichloro-dibenz[b,f][1,4]-oxazepines as the primary products. Mechanisms of the primary and subsequent reactions are discussed.