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

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

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 a...

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Veröffentlicht in:Synlett 2005-01, Vol.2005 (1), p.49-54
Hauptverfasser: Bi, Xihe, Liu, Qun, Sun, Shaoguang, Liu, Jun, Pan, Wei, Zhao, Lei, Dong, Dewen
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-836034