Novel Domino Reactions of (Z,Z)-2,2′-Thiobis(1,3-diarylprop-2-en-1-ones) with Acetylacetone and Ethyl Acetoacetate: Stereoselective Synthesis of Highly Functionalized Dihydrofurans

Abstract

The domino reactions of (Z,Z)-2,2′-thiobis(1,3-diarylprop-2-en-1-ones) with acetylacetone and ethyl acetoacetate in the presence of sodium ethoxide afforded the corresponding 4,5-dihydrofurans stereoselectively in moderate yields presumably via a Michael addition–enolization–displacement sequence.

Keywords:

• Dihydrofurans
• domino reactions
• stereoselective synthesis
• 2,2′-thio-bis(1,3-diarylprop-2-en-1-ones)

ACKNOWLEDGMENTS

S. R. and M. G. thank the University Grants Commission for the financial support under Major Research Project F. 31-96/2005 (SR). S. R. and M. G. also thank the secretary and the principal, Fatima College, Madurai, for providing facilities.

Notes

^a The ratio of 1–ketone–NaOEt is 1:2:2.

^b The ratio of 1–ketone–NaOEt is 1:1:1.

^c Melting points of 3 agree with those reported in the literature.