stereoselective synthesis of cis-substituted-3’-anilino-2’, 3’-dihydro-4-2’-benzo[b]furanylcoumarins via intramolecular aldol reactions立体选择合成cis-substituted-3 -anilino-2,3u2018-dihydro-4-2苯并[b]furanylcoumarins通过分子内醇醛反应.pdf

International Journal of Organic Chemistry, 2012, 2, 44-48 / 10.4236/ijoc.2012.21008 Published Online March 2012 (http://www.SciRP.org/journal/ijoc) Stereoselective Synthesis of cis-Substituted-3’-anilino-2’, 3’-dihydro-4-2’-benzo[b]furanylcoumarins via Intramolecular Aldol Reactions 1 1 1* Lokesh A. Shastri , Samundeeswari L. Shastri , Manohar V. Kulkarni , Vivek K. Gupta2, Sanjeev Goswami2 1P. G. Department of Chemistry, Karnatak University, Dharwad, India 2P. G. Department of Physics, University of Jammu, Jammu Tawi, India * Email: chemilok@yahoo.co.in Received December 12, 2011; revised January 24, 2012; accepted February 9, 2012 ABSTRACT The present study reports the reaction of 4-bromomethylcoumarins with salicylidineaniline in acetone with two equiva- lents of potassium carbonate resulted in the formation of title compounds at room temperature via intramolecular al- dolization. The obtained compound is thermodynamically and kinetically stable with highly stereoselective and excel- lent yield. Keywords: Aldol Reaction; Stereoselective; Intramolecular; Mild Base; 4-Bromomethylcoumarins; Dihydrobenzofurans 1. Introduction of the nucleophiles possess electron-rich heteroatoms or aromatic rings. Therefore the electrolytic potential is The 2,3-dihydrobenzofuran skeleton has been associated