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

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 TMSNMe 2 and MgBr 2 ˙OEt 2 under solvent-free conditions. The main ad...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2011-12, Vol.2011 (23), p.3821-3826
Main Authors: Mojtahedi, Mohammad M., Abaee, M. Saeed, Khakbaz, Mehdi, Alishiri, Tooba, Samianifard, Maedeh, Mesbah, A. Wahid, Harms, Klaus
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary: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 TMSNMe 2 and MgBr 2 ˙OEt 2 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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1289571