The cyclization of acetylated β-iminonitriles: 4-amino-2-hydroxy-6, 7-dihydropyrindine

HE Schroeder, GW Rigby

Index: Schroeder; Rigby Journal of the American Chemical Society, 1949 , vol. 71, p. 2205,2207

Full Text: HTML

Citation Number: 23

Abstract

The 3-position ortho to both the hydroxyl and amino groups is reactive. Bromination or chlorination in cold glacial acetic proceeds instantaneously to form the 3-bromo tXV) or 3- chloro (VI) derivatives in high yield. Diazotized aromatic amines couple readily to yield the corresponding azo compounds and reaction with benzaldehyde (or formaldehyde) proceeds smoothly as in the case of m-aminophenol to give a dipyrido-pyridine derivative (XVI). ...