Journal of Organic Chemistry p. 5144 - 5149 (1980)
Update date:2022-08-04
Topics:
Agarwal, Nand L.
Schaefer, Wolfram
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).
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Doi:10.1016/S0040-4039(00)92728-X
(1980)Doi:10.1021/ja00877a005
(1962)Doi:10.1021/jacs.7b02742
(2017)Doi:10.1002/ejic.200300774
(2004)Doi:10.1016/S0040-4039(00)71389-X
(1980)Doi:10.1039/DT9800001228
(1980)