Journal of the Chemical Society. Perkin transactions I p. 1359 - 1364 (1996)
Update date:2022-08-03
Topics:
Beccalli, Egle M.
Erba, Emanuela
Gelmi, Maria Luisa
Pocar, Donato
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-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 intermediates were shown in certain cases to be 5-amino-v-triazolines 5 and 10 undergoing thermal rearrangement to amidines 7 and 11 followed by intramolecular base-catalysed cyclocondensation.
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