Aza-Wittig reaction of N-phosphorylalkyl phosphazenes with carbonyl compounds and phenylisocyanate. Synthesis of 4-amino-3-phosphoryl-2-azadienes and pyrazine-phosphonates

作者：Palacios F^*; de Retana AMO; de Marigorta EM; Rodriguez M; Pagalday J

来源：Tetrahedron, 2003, 59(15): 2617-2623.

DOI：10.1016/S0040-4020(03)00337-5

• phosphazenes
• Aza-Wittig
• aminophosphonates
• azadienes
• pyrroles
• pyrazines

Simple and functionalized N-phosphorylalkyl imines and N-phosphorylalkyl-N'-phenyl-carbodiimides are obtained by aza-Wittig reaction of phosphazenes derived from aminophosphonates with carbonyl compounds and phenyl isocyanate. The reaction with dimethylformamide diethyl acetal (DMF-DEA) of these functionalized imines leads to the synthesis of 4-amino-3-phosphoryl-2-azadienes. N-Phosphorylmethyl imine derived from benzaldehyde can be used for the preparation of substituted pyrrole-phosphonates, while acid treatment of 4-dimethylamino-3-diethylphosphoryl-1-phenyl-2-azadiene gives diethyl 5-diethylphosphorylpyrazin-2-ylphosphonate.

• 出版日期2003-4-7