A facile and efficient synthesis of 3,5-disubstituted tetronic acids in aqueous media involving acid-catalyzed intramolecular oxa-pyridylethylation

被引：24

作者：

Bi, XH ^{[1
]}

Liu, Q ^{[1
]}

Sun, SG ^{[1
]}

Liu, J ^{[1
]}

Pan, W ^{[1
]}

Zhao, L ^{[1
]}

Dong, DW ^{[1
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

来源：

SYNLETT | 2005年 / 01期

关键词：

aqueous media; tetronic acid derivatives; alpha-oxo ketene-S; S-acetals; oxa-pyridylethylation; alpha-oxo ketene-N; N-acetals;

D O I：

10.1055/s-2004-836034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha-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.

引用

页码：49 / 54

页数：6

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