Abstract
A three-component reaction of trialkyl(aryl) phosphites, dialkyl acetylenedicarboxylates and rhodanine is described as a simple and efficient route for synthesis of dialkyl 2-(dialkoxyphosphoryl)-3-(4-oxo-4,5-dihydro-thiazole-2-yl sulfanyl) succinates in good yields. Protonation of the reactive 1:1 intermediate produced in the reaction between dialkyl acetylenedicarboxylate and triphenylphosphine by N′-formylbenzohydrazide leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of the NH acid to produce highly functionalized, salt-free phosphorus ylides in excellent yields.
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