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Communication | Special issue | Vol 50, No. 2, 1999, pp.645-652
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)83
An Efficient Synthesis of 5-Phosphorylated 1,3,2-Diazaphosphinines from β-Functionalized Enamines Derived from Phosphine Oxides and Phosphonates

Francisco Palacios,* Domitila Aparicio, Jesús M. de los Santos, and Jesús García

*Departamento de Química OrgÁnica, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria-Gasteiz, Spain


An easy and efficient synthesis of 1,3,2-PIII-diazaphosphininones (3,4) substituted with a phosphine oxide or a phosphonate group in the 5-position is described. The key step is a cyclocondensation reaction of substituted β-enamino amides (1) to phosphorus trichloride and phenylphosphonous dichloride. Subsequent treatment of 1,3,2-PIII-diazaphosphininones (3) with elemental sulfur, water or hydrogen peroxide afforded the substituted 2-thio-(7,8) and 2-oxo-1,3,2-PV-diazaphosphininones (5,6,9).