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Synthesis 2011(23): 3821-3826  
DOI: 10.1055/s-0031-1289571
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Procedure for the Synthesis of α,β-Unsaturated Ketones and Its Application to Heterocyclic Systems

Mohammad M. Mojtahedi*a, M. Saeed Abaee*a, Mehdi Khakbaza, Tooba Alishiria, Maedeh Samianifarda, A. Wahid Mesbaha, Klaus Harmsb
a Department of Organic Chemistry, Chemistry & Chemical Engineering Research Center of Iran, P. O. Box 14335-186, Tehran, Iran
Fax: ++98(21)44580762; e-Mail: mojtahedi@ccerci.ac.ir; e-Mail: abaee@ccerci.ac.ir;
b Fachbereich Chemie der Philipps-Universität Marburg, Hans-Meerwein-Str., 35032 Marburg, Germany
Further Information

Publication History

Received 1 September 2011
Publication Date:
20 October 2011 (online)

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Abstract

An efficient and room-temperature procedure is developed for high yield synthesis of novel α,β-unsaturated derivatives of thiopyran 3 directly from ketone 1 and various aldehydes in the presence of catalytic quantities of TMSNMe2 and MgBr2˙OEt2 under solvent-free conditions. The main advantage of the procedure is that the formation of the undesired bis by-products is minimized. In addition, the procedure is applicable to other enolizable carbocyclic and acyclic ketones.

Key words

α,β-unsaturated ketones - thiopyran-4-one - magnesium bromide etherate - aldol condensation

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Crystallographic data for 3i have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-846075. Copies of these data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk or via www.ccdc.cam.ac.uk/conts/retrieving.html].