v-Triazolines. Part 37. Rearrangement reactions of 5-amino-1-(2-formyl-, -benzoyl-, -cyano-aryl)-ν-triazolines: new synthesis of 2-amino- and 2,4-diamino-quinolines and 2,4-diamino-1,7-naphthyridines

Abstract

2-Aminoquinolines 4 were obtained in an one-pot reaction from arylacetaldehydes 1, secondary amines 2 and aryl azides 3 in refluxing benzene or xylene. 2,4-Diaminoquinolines and 2,4-diamino-l,7-naphthyridines 9 were prepared by heating arylacetaldehydes 1 with secondary amines 2 and aryl or pyridyl azides 8 and reaction with bases. Reaction intermediates were shown in certain cases to be 5-amino-ν-triazolines 5 and 10 undergoing thermal rearrangement to amidines 7 and 11 followed by intramolecular base-catalysed cyclocondensation.