1,3-DIPOLAR CYCLOADDITIONS OF AZIDOALKYL-PHOSPHONATES TO ENAMINES - SYNTHESIS OF DELTA(2)-1,2,3-TRIAZOLINES AND TRIAZOLES

Authors
PALACIOS F DERETANA AMO PAGALDAY J
Citation
F. Palacios et al., 1,3-DIPOLAR CYCLOADDITIONS OF AZIDOALKYL-PHOSPHONATES TO ENAMINES - SYNTHESIS OF DELTA(2)-1,2,3-TRIAZOLINES AND TRIAZOLES, Heterocycles, 40(2), 1995, pp. 543-550
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
40
Issue
2
Year of publication
1995
Pages
543 - 550
Database
ISI
SICI code
0385-5414(1995)40:2<543:1COATE>2.0.ZU;2-I
Abstract
5-Amino-Delta 2-1,2,3-triazolines (3) and 1,2,3-triazoles (4) and (8) derived from aminoalkylphosphonates have been obtained in a regioselec tive fashion, by treating diethyl azidoalkylphosphonates (1) with enam ines (2) and (6). Reaction of azidomethylphosphonate (1) with an exces s of norbornadiene yields triazoline (10). This monoadduct undergoes n itrogen evolution and retro Diels-Alder reaction to give aziridine (11 ) and triazole (12), respectively.