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DOI: 10.1055/s-0032-1316837
Regio- and Diastereoselective Synthesis of trans-2,3-Dihydrofuran Derivatives in an Aqueous Medium
Publication History
Received: 07 October 2012
Accepted after revision: 05 December 2012
Publication Date:
04 January 2013 (online)
This work is dedicated to Professor K. C. Majumdar, Department of Chemistry, Kalyani University, West Bengal, India on the occasion of his 68th birthday.
Abstract
A wide variety of fused trans-2,3-dihydrofuran derivatives were synthesized through a one-pot three-component reaction of an aromatic aldehyde, a cyclic β-diketo compound, and an in situ-generated pyridinium ylide in refluxing. The pyridinium ylide was formed from either 2-bromo-1-phenylethanone or 4-nitrobenzyl bromide and pyridine in the presence of 10 mol% of sodium hydroxide. Pyridine plays crucial role in forming the pyridinium salt, which, in turn, forms a nitrogen ylide in the presence of sodium hydroxide. The ylide assists a Michael-initiated ring-closure reaction, but is not itself incorporated in the final product. The protocol is environmentally acceptable because no organic solvent is involved at any stage. Furthermore, the method is highly diastereoselective, gives good yields, and does not involve extensive workup procedures or chromatographic separations, as the desired products can be isolated by filtration and drying.
Key words
furans - heterocycles - cyclizations - multicomponent reactions - green chemistry - regioselectivity - diastereoselectivitySupporting Information
- for this article is available online at: http://www.thieme-connect.com/ejournals/toc/synthesis. Included are X-ray crystallographic data and CIF files of 6e, spectral data for all compounds, and copies of 1H and 13C NMR and HRMS spectra of products associated with this article.
- Supporting Information
Primary Data
- for this article are available online at http://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0038th
- Primary Data
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