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Synfacts 2011(4): 0367-0367  
DOI: 10.1055/s-0030-1259674
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Base-Mediated Synthesis of 4,5-Disub-stituted Furan-2(5H)-ones

Contributor(s): Victor Snieckus, Toni Rantanen
Y. Lei, Z.-Q. Wang, Y.-X. Xie, S.-C. Yu, B.-X. Tang, J.-H. Li*
Hunan Normal University, Changsha and Wenzhou University, P. R. of China
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

Reported is a route to furan-2(5H)-ones by cyclization of acetyl propargylic esters, involving an intriguing acyl shift, cyclization and decarbonylation sequence. The starting materials can be synthesized from the corresponding alkyne carboxylic acids and 2-haloacetophenones. Reaction conditions are mild, the substrate scope is quite good, and the yields range from poor to excellent. The reaction fails when R² = Alk. Refreshingly, proof for the mechanism involving deuterium (both solvent and substrate) and ¹³C labeling, isolation, and successful reaction of the cyclized pre-decarbonylation product is provided.