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Short Paper | Regular issue | Vol 85, No. 12, 2012, pp.2987-2998
Published online, 25th October, 2012
DOI: 10.3987/COM-12-12581
Preparation of β-Keto-β-alkanoyloxyphosphonates, Phosphine Oxides and Sulfides and Their Application to the Synthesis of Novel Phosphoryl- and Thiophosphorylpyrazoles

Hosni Slimani and Soufiane Touil*

*Department of Chemistry, Faculty of Sciences of Bizerta, 7021-Jarzouna, Tunisia


Two synthetic methods leading to β-keto-β-alkanoyloxyphosphonates, phosphine oxides and sulfides 2 are reported. The first method involves the reaction of β-enaminoesters 1 with chlorophosphines and phosphites followed by oxidation or sulfurization and hydrolytic work-up. The second one utilizes the reaction of β-enaminoesters 1 with diethylchlorophosphate and thiophosphate followed by acid hydrolysis. On reaction with hydrazine derivatives, compounds 2 give the corresponding phosphoryl- and thiophosphorylpyrazoles 3. The structures of all obtained products were confirmed by NMR (1H, 31P, 13C) and IR spectroscopies, and by mass spectrometry.