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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 5
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Original Articles

Platinum(II)-Catalyzed Novel Synthesis of 3,4-Fused Furans

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Pages 625-634 | Received 21 Aug 2014, Published online: 12 Jan 2015
 

Abstract

A novel synthesis of 3,4-fused furans (both tricyclic and bicyclic) through platinum-catalyzed cyclization of 3-(2-formylcycloalkenyl)-acrylic amides 2 in methanol is described (up to 90% yield). Tricyclic 3,4-fused dihydrofuran derivatives were also obtained via reductive cyclization of 2. The substrates 2 were obtained from β- bromovinyl aldehydes by a Pd-catalyzed Heck reaction.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We are grateful to the Chemistry Department of Jadavpur University for the facilities for NMR spectroscopy, Atanu Jana for his expertise in x-ray crystollagraphy, and Arup Kumar Adak and Biswanath Mondal for constant inspiration.

SUPPORTING INFORMATION

Electronic supplementary information (ESI) (1H and 13C spectra of representative compounds) for this article and can be accessed on the publisher’s website.

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