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Communication | Special issue | Vol 40, No. 2, 1995, pp.543-550
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S83
1,3-Dipolar Cycloadditions of Azidoalkylphosphonates to Enamines. Synthesis of Δ2-1,2,3-Triazolines and Triazoles

Francisco Palacios, Ana Ma Ochoa de Retana, and Jaione Pagalday

*Departamento de Química Orgánica, Facultad de Farmacia, Universidad del País, Vasco, Apto. 450, 01006 Vitoria, Spain

Abstract

5-Amino-Δ2-1,2,3-triazolines (3) and 1,2,3-triazoles (4) and (8) derived from aminoalkylphosphonates have been obtained in a regioselective fashion, by treating diethyl azidoalkylphosphonates (1) with enamines (2) and (6). Reaction of azidomethylphosphonate (1) with an excess of norbornadiene yields triazoline (10). This monoadduct undergoes nitrogen evolution and retro Diels-Alder reaction to give aziridine (11) and triazole (12), respectively.