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Synthesis 2002(17): 2537-2541
DOI: 10.1055/s-2002-35627
PAPER
© Georg Thieme Verlag Stuttgart · New York

Scandium Triflate Immobilized in Ionic Liquids: A Novel and Recyclable Catalytic­ System for Hetero-Diels-Alder Reactions

J. S. Yadav*, B. V. S. Reddy, K. Uma Gayathri, A. R. Prasad
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)7160512; e-Mail: yadav@iict.ap.nic.in;
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Publication History

Received 14 June 2002
Publication Date:
20 November 2002 (online)

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Abstract

Cyclic enol ethers such as 3,4-dihydro-2H-pyran (DHP) and 2,3-dihydrofuran (DHF) undergo [4+2] cycloaddition reactions with imines (generated in situ from aryl amines and enol ethers) in the presence of 3 mol% scandium triflate immobilized in 1-butyl-3-methylimidazolium hexafluorophosphate under solvent-free conditions to afford the corresponding pyrano- and furo[3,2-c]quinolines in high yields.

Key words

ionic liquids - scandium triflate - hetero-Diels-Alder reaction - cis-fused tetrahydroquinolines