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Synthesis of Phostams and Phosptones from Phosphenes and Their Equivalents

Phosphene; Phostam; Phostone

Phostams and phostones are phosphorus analogs of lactams and lactones. They are important biologically active compounds and have been widely applied as enzyme inhibitors, agrochemicals, and medicines. Both β-phosphinolactams and benzo-δ-phosphinolactams were synthesized from linear and cyclic imines with aryl(diazo)methyl(diaryl)phosphine oxides. Benzo-δ-phosphonolactams were prepared from cyclic imines and ethyl arylmethylphosphonochloridates. However, the reaction of various imines and ethyl non-arylmethylphosphonochloridates generated a,β-unsaturated phosphonamidates. Both δ-phosphinolactones andδ-phosphonolactones were obtained from phosphinyl chlorides and phosphonochloridates with a,β-enones. All reactions work well, giving the desired products in good yields.