Tetrahedron

Reaction of diazomethane with 5-hydroxy-4-phenylabonzofurazan as a synthetic route to derivatives of a new heterocycle—pyrazolo [3, 4-f]-1, 2, 3-benzotriazole

V Cerè, S Pollicino, E Sandri, G Scapini

Index: Cere,V. et al. Tetrahedron, 1976 , vol. 32, p. 1277 - 1281

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Abstract

Diazomethane adds to 5-hydroxy-4-phenylazobenzofurazan 1 giving a compound 3 which rearranges in alkaline solution to the 8-monoxime of 2-phenyl-5 (6) H-pyrazolo [3, 4-f]-1, 2, 3- benzotriazole-4, 8-dione 4, the structure of which has been demonstrated by chemical and spectroscopic methods. The probable structure of adduct 3 is discussed on the basis of the chemical reactivity of the compound. The orientation of the cycloaddition and the ...