Chemoselective synthesis of phosphorus ylides through the reaction of 2-mercaptobenzimidazole and 2-hydroxybenzimidazole with triphenylphosphine and acetylenic esters

Abstract

A one-step synthesis of dialkyl 2-(2-mercaptobenzimidazole-s-yl)-3-(triphenylphosphoranyliden) succinates and dialkyl 2-(2-hydroxybenzimidazole-n-yl)-3-(triphenylphosphoranyliden) succinates in fair yields are reported through the reaction of dialkyl acetylenedicarboxylates and triphenylphosphine in the presence of 2-mercaptobenzimidazole or 2-hydroxybenzimidazole.

Keywords:

• Chemoselective
• Acetylenic esters
• 2-Mercaptobenzimidazole
• Triphenylphosphine
• Stable phosphorus ylide
• Geometrical isomers

Acknowledgements

We gratefully acknowledge financial support from the Research Council of University of Sistan and Balouchestan.