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Short Paper | Regular issue | Vol 85, No. 11, 2012, pp.2765-2774
Published online, 2nd October, 2012
DOI: 10.3987/COM-12-12570
Behaviour of β-Keto-δ-carbethoxyphosphonates and Phosphine Oxides in the Biginelli Multicomponent Reaction: Regioselective Synthesis of 5-Carbethoxy-6-phosphonomethyl-3,4-dihydropyrimidin-2-ones

Emna Chebil and Soufiane Touil*

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

Abstract

An efficient one-pot synthesis of the novel 5-carbethoxy-6-phosphonomethyl-3,4-dihydropyrimidin-2-ones via a three-component Biginelli-type condensation of β-keto-δ-carbethoxyphosphonates and phosphine oxides with aldehydes and urea in the presence of a catalytic amount of acetic acid, is described. The reaction proceeded efficiently at room temperature to afford regioselectively the title compounds in good to high yields. The factors governing the regioselectivity of the reaction are discussed.