2.

A Facile, Choline Chloride/Urea Catalyzed Solid Phase Synthesis of Coumarins via Knoevenagel Condensation

Hosanagara N. Harishkumar , Kittappa M. Mahadevan , Hittalumane C. Kiran Kumar and Nayak D. Satyanarayan

Org. Commun. (2011), 4:2 ; 26-32

Department of Post Graduate Studies and Research in Chemistry, School of Chemical Sciences Kuvempu University, Shankaraghatta, Karnataka, India.

Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Center, Kadur-577 548, Karnataka 577451, India.

Abstract: The influence of choline chloride/urea ionic liquid in solid phase on the Knoevenagel condensation is demonstrated. The active methylene compounds such as meldrum’s acid, diethylmalonate, ethyl cyanoacetate, dimethylmalonate, were efficiently condensed with various salicylaldehydes in presence of choline chloride/urea ionic liquid without using any solvents or additional catalyst. The reaction is remarkably facile because of the air and water stability of the catalyst, and needs no special precautions. The reactions were completed within 1hr with excellent yields (95%). The products formed were sufficiently pure, and can be easily recovered. The use of ionic liquid choline chloride/urea in solid phase offered several significant advantages such as low cost, greater selectivity and easy isolation of products.

Keywords: Knoevenagel condensation;coumarins; choline chloride/urea; meldrum’s acid; ionic liquid.