Preparation of Substituted 2H-Pyrans via a Cascade Reaction from Methyl Coumalate and Activated Methylene Nucleophiles

被引：17

作者：

Chang, Liang ^{[1
]}

Plevova, Kristina ^{[1
]}

Thorimbert, Serge ^{[1
]}

Dechoux, Luc ^{[1
]}

机构：

[1] UPMC Univ Paris 06, Sorbonne Univ, UMR CNRS 8232, Inst Parisien Chim Mol, 4 Pl Jussieu, F-75005 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 10期

关键词：

PROPARGYL VINYL ETHERS; ONE-POT SYNTHESIS; 3+3 ANNULATIONS; ELECTROCYCLIZATION; SOLVENT; ACID; 2H-PYRAN-5-CARBOXYLATES; CYCLOISOMERIZATION; (E; Z)-DIENALS; CONSTRUCTION;

D O I：

10.1021/acs.joc.7b00761

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of methyl coumalate with a wide range of methylene active compounds, such as keto-esters or keto-sulfones and cyclic or acyclic diketones, afforded more than 30 2,3,5,6-tetrasubstituted 2H-pyrans. The reaction proceeds via a cascade reaction involving a Michael addition-6 pi-electrocyclic ring opening-proton transfer and 6 pi electro-cyclization, in which a variety of functional groups were tolerated.

引用

页码：5499 / 5505

页数：7

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