Quinone Chemistry. Reaction of 2,3-Dichloro-1,4-naphthoquinone with 2-Aminophenols in Pyridine

Article abstract of DOI:10.1021/jo01313a024

The reaction of 2,3-dichloro-1,4-naphthoquinone (1) and 2-aminophenols (2) in pyridine furnished substituted 6-chloro-5H-benzophenoxazin-5-one (10), 5H-benzophenoxazin-5-one (8), 5H-benzophenoxazin-5-one-6-pyridinium chloride (6), 2-(2-hydroxyanilino)-1,4-naphthoquinone-3-pyridinium chloride (5), and 12H-benzophenoxazine-6,11-dione (7).It was observed that the nature and yields of the reaction products were greatly influenced by the substituent present in 2.The reaction mechanism for the formation of all products is discussed, and spectroscopic data are also given.This reaction for the first time led to a development of a novel, convenient synthesis of a new class of heterocyclic quinones (7).