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.

v-Triazolines. Part 37. Rearrangement reactions of 5-amino-1-(2-formyl-, -benzoyl-, -cyano-aryl)-v-triazolines: New synthesis of 2-amino- and 2,4-diamino-quinolines and 2,4-diamino-1,7-naphthyridines / E.M. Beccalli, E. Erba, M.L. Gelmi, D. Pocar. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 12(1996), pp. 1359-1364.

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

E.M. Beccalli
Primo
;
E. Erba
Secondo
;
M.L. Gelmi
Penultimo
;
D. Pocar
Ultimo
1996

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-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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/181866
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