Synlett 2005(1): 49-54  
DOI: 10.1055/s-2004-836034
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Facile and Efficient Synthesis of 3,5-Disubstituted Tetronic Acids in Aqueous Media Involving Acid-Catalyzed Intramolecular Oxa-Pyridylethylation

Xihe Bi, Qun Liu*, Shaoguang Sun, Jun Liu, Wei Pan, Lei Zhao, Dewen Dong*
Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. China
e-Mail: dongdw663@nenu.edu.cn;
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Publication History

Received 25 August 2004
Publication Date:
29 November 2004 (online)

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Abstract

A facile and efficient one-pot synthesis of 3-[bis(alkyl­thio/alkylamino)methylene]-5-(pyridyl/quinoylmethyl) furan-2,4(3H,5H)-diones 3 and 10, based on a sequential aldol condensation and lactonization reaction between α-oxo ketene-S,S-acetals 1 and pyridine/qinoline-carboxaldehydes 2 in aqueous media, has been developed. A mechanism involving an acid-catalyzed intramolecular oxa-pyridylethylation reaction is proposed for the ­formation of the lactone ring.

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