Tetrahedron Letters

N-Aryl-2-nitrosoanilines as intermediates in the synthesis of substituted phenazines from nitroarenes

A Kwast, K Stachowska, A Trawczyński, Z Wróbel

Index: Kwast, Andrzej; Stachowska, Karolina; Trawczynski, Adam; Wrobel, Zbigniew Tetrahedron Letters, 2011 , vol. 52, # 48 p. 6484 - 6488

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Citation Number: 22

Abstract

N-Aryl-2-nitrosoanilines, available from the reaction of nitroarenes with anilide anions, undergo cyclization to furnish substituted phenazines. The reaction is promoted by potassium carbonate in methanol, N, O-bis (trimethylsilyl) acetamide (BSA) in aprotic solvents, and by acetic acid. The method is illustrated by the synthesis of 1- methoxyphenazine, a precursor of pyocyanine, starting from the appropriate nitroarene– ...