Synthesis of new functionalized maleimides and phthalimides from maleimide, phthalimide, acetylenicesters, and phosphorus nucleophiles

Abstract

An efficient and convenient three-component reaction of dialkyl acetylene dicarboxylates with trialkyl(aryl) phosphites in the presence of maleimide or phthalimide provides a straightforward approach to the synthesis of stable dialkyl(aryl) phosphoryl succinates in excellent yields. While the reactions were carried out in the presence of triphenylphosphine, stabilized phosphoranes, obtained from three component reaction, undergo a smooth intramolecular Wittig reaction in boiling toluene to produce functionalized 2H-pyrrol-2-ones in good yields.

Graphical Abstract

Keywords:

• Maleimide
• phthalimide
• acetylenic esters
• trialkyl(aryl) phosphites
• triphenylphosphine