NU-TRIAZOLINES .37. REARRANGEMENT REACTIONS OF 5-AMINO-1-(2-FORMYL-ARYL)-NU-TRIAZOLINE, 5-AMINO-1-(2-BENZOYL-ARYL)-NU-TRIAZOLINE, 5-AMINO-1-(2-CYANO-ARYL)-NU-TRIAZOLINE - NEW SYNTHESIS OF 2-AMINO-QUINOLINE AND2,4-DIAMINO-QUINOLINE AND 2,4-DIAMINO-1,7-NAPHTHYRIDINES

2-Aminoquinolines 4 were obtained in an one-pot reaction from arylacet aldehydes 1, secondary amines 2 and aryl azides 3 in refluxing benzene or xylene, 2,4-Diaminoquinolines and 2,4-diamino-1,7-naphthyridines 9 were prepared by heating arylacetaldehydes 1 with secondary amines 2 and aryl or pyridyl azides 8 and reaction with bases, Reaction interme diates were shown in certain cases to be 5-amino-v-triazolines 5 and 1 0 undergoing thermal rearrangement to amidines 7 and 11 followed by in tramolecular base-catalysed cyclocondensation.