Exploiting the Divergent Reactivity of α-Isocyanoacetate: Multicomponent Synthesis of 5-Alkoxyoxazoles and Related Heterocycles

被引：73

作者：

Lalli, Claudia ^{[1
]}

Bouma, Marinus J. ^{[1
]}

Bonne, Damien ^{[1
,2
]}

Masson, Geraldine ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] Aix Marseille Univ, Inst Sci Mol Marseille, CNRS,Ctr St Jerome Serv 531, UMR 6263 iSm2, F-13397 Marseille 20, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 03期

关键词：

Diels-Alder reaction; isocyanoacetates; multicomponent reactions; oxygen heterocycles; sustainable chemistry; DIELS-ALDER REACTIONS; ONE-POT SYNTHESIS; PROMOTED 3-COMPONENT SYNTHESIS; KONDRATEVA PYRIDINE SYNTHESIS; BIFUNCTIONAL BUILDING-BLOCKS; TERMINAL CARBOXYLIC-ACID; ORGANIC-SYNTHESIS; CYCLOADDITION REACTIONS; ASYMMETRIC-SYNTHESIS; AMINO-ACID;

D O I：

10.1002/chem.201002098

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel multicomponent synthesis of 5-alkoxyoxazoles, based on a new reactivity profile of alpha-isocyanoacetates, is described. Thus, simply heating a solution of amine, aldehyde, and alpha-(EWG-phenyl)-alpha-isocyanoacetate or alpha-(4-pyridyl)-alpha-isocyanoacetate (EWG = electron-withdrawing group) in toluene provided 5-alkoxyoxazoles in good to excellent yields. Reaction of the 5-alkoxyoxazoles with various alpha,beta-unsaturated acyl chlorides led to the formation of epoxytetrahydropyrrolo-[3,4-b]pyridin-5-ones by a domino N-acylation/Diels-Alder cycloaddition sequence. Subsequent fragmentation under basic conditions provided 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. A four-component synthesis of the pyridin-5-one compounds, without isolation of the 5-alkoxyoxazole, was subsequently developed.

引用

页码：880 / 889

页数：10

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