Paper
A new ring closure reaction of 2-phenoxyphenols and 3-(phenoxy)pyridines. Synthesis of halogenated 10-methylphenoxazines and 10-methyl[1,4]benzoxazino[3,2-b]pyridines
Published Sep 1, 1979 · H. Fuhrer, P. Sutter, C. Weis
Journal of Heterocyclic Chemistry
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Abstract
The cyclization of 2-(2-chloro(bromo)phenoxy)anilines and 3-(phenoxy)pyridines to 10-methylphenoxazines and 10-methyl[1,4]benzoxazino[3,2-b]pyridines, respectively, by means of dimethyl methylphosphonate is reported. The cyclization reaction proceeded with expulsion of methyl ether. Demethylation of some 10-methylphenoxazines was achieved with pyridine hydrobromide. Nitration was carried out with sodium nitrite, and by reduction of the nitro groups the corresponding amines were prepared.
This study presents a new ring closure reaction for 2-phenoxyphenols and 3-(phenoxy)pyridines, resulting in 10-methylphenoxazines and 10-methyl[1,4]benzoxazino[3,2-b]pyridines, with potential applications in organic synthesis.
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