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Paper | Regular issue | Vol 94, No. 5, 2017, pp.894-911
Published online, 18th April, 2017
DOI: 10.3987/COM-17-13687
■ Synthesis of γ-Keto-δ-alkenyl-phosphonates and Phosphine Oxides as Precursors of Novel Phosphono-pyrazoline and pyrazole Derivatives

Imen Lamouchi and Soufiane Touil*

*Laboratory of Heteroatom Organic Chemistry, Faculty of Sciences of Bizerte, University of Carthage, 7021-Jarzouna, Tunisia

Abstract

Herein we report the synthesis of γ-keto-δ-alkenyl-phosphonates and phosphine oxides by two versions of strategy (a) which involves the addition of dialkyl phosphites to α,α’-diarylideneketones, and by strategy (b) which utilizes the reaction of P-chlorodiphenylphosphine with diarylidene ketones in acetic acid. On reaction with hydrazine derivatives, γ-keto-δ-alkenyl-phosphonates and phosphine oxides give 3-phosphonoethylpyrazoline derivatives which can be converted into the corresponding aromatic pyrazoles by oxidative dehydrogenation, using sodium nitrite as oxidizing agent.