Abstract

Several kinds of 1-methoxy-chlorophenazines were prepared by the Wohl-Aue reaction and it was found that N-oxides formed as a by-product in some cases. 1-Methoxy-6-chlorophenazine was prepared by the condensation of 2-nitro-1-chlorobenzene and o-anisidine, and 1-methoxy-8-chlorophenazine by the condensation of p-chloroaniline and o-nitroanisole, but formation of N-oxide was not observed in this case.Condensation of 3-nitro-1-chlorobenzene and o-anisidine afforded the 1-methoxy-7-chloro and 1-methoxy-9-chloro compounds, and the N-oxide of the latter. Condensation of m-chloroaniline and o-nitroanisole afforded 1-methoxy-9-chlorophenazine, and that of o-chloroaniline and m-nitroanisole gave 1-methoxy-9-chloro compound and 1-methoxyphenazine 5-oxide. Condensation of p-chloroaniline and m-nitroanisole afforded 1-methoxy-7-chlorophenazine and its 5-oxide, 2-chlorophenazine 10-oxide, and 2-methoxy-8-chlorophenazine 10-oxide.

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