Issue 0, 1972

The chemistry of nitro-compounds. Part II. The scope and mechanism of the base-catalysed transformations of someNN-disubstituted o-nitrobenzamides

Abstract

In reactions explicable by the intermediate formation of 2-cyanoquinazolone N-oxides (2), hot ethanolic sodium ethoxide converts the N-cyanomethyl-o-nitrobenzamides (1a–c) in high yield into the N-hydroxyquinazolinediones (3a–c). In contrast, treatment of the N-benzoylmethyl-amide (6a) or the N-ethoxycarbonylmethyl-amide (6b) with ethanolic sodium ethoxide affords the indazolone (13a). The indazolones (13a and b) are formed under similar conditions from the N-α-cyanoethyl-amides (8a and b). On the other hand, hot aqueous ethanolic sodium carbonate converts the amide (8a) into a mixture of the indazolone (13a) and NN′-diphenylazobenzene-2,2′-di-carboxamide (15a); similar treatment of the amide (8b) affords the corresponding azoxybenzene derivative (16b) and benzaldehyde 2-carboxyphenylhydrazone (20). Mechanisms for the base-catalysed transformations of the amides (6a and b) and (8a and b) are discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 97-102

The chemistry of nitro-compounds. Part II. The scope and mechanism of the base-catalysed transformations of someNN-disubstituted o-nitrobenzamides

T. W. M. Spence and G. Tennant, J. Chem. Soc., Perkin Trans. 1, 1972, 97 DOI: 10.1039/P19720000097

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