One-pot synthesis of functionalized benzo[c]-coumarins and their precursors via the reaction of 2-(polyfluoroalkyl)chromones with 4-alkyl-3-cyanocoumarins

被引：5

作者：

Sosnovskikh, Vyacheslav Ya. ^{[1
]}

Korotaev, Vladislav Yu. ^{[1
]}

Kutyashev, Igor B. ^{[1
]}

Barkov, Alexey Yu. ^{[1
]}

Safrygin, Alexander V. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci, Ekaterinburg 620000, Russia

来源：

RSC ADVANCES | 2016年 / 6卷 / 63期

基金：

俄罗斯基础研究基金会;

关键词：

1,3-BIS(SILYL ENOL ETHERS); REGIOSELECTIVE SYNTHESIS; HETEROCYCLIC SYNTHESIS; MEDICINAL CHEMISTRY; PRIVILEGED SCAFFOLD; EFFICIENT SYNTHESIS; DOMINO REACTIONS; DERIVATIVES; 2-POLYFLUOROALKYLCHROMONES; COUMARINS;

D O I：

10.1039/c6ra12492e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-(Polyfluoroalkyl) chromones react with 4-alkyl-3-cyanocoumarins in dichloromethane in the presence of triethylamine to give a wide variety of functionalized benzo[c] coumarin derivatives in good yields. This new annulation reaction presumably proceeds by a tandem intermolecular Michael addition and subsequent intramolecular condensation between an intermediate enolate anion and cyano group. In the case of 3-cyano-4-methylcoumarin and 2-(trifluoromethyl) chromones activated by two electron-withdrawing substituents, three acyclic intermediates were isolated and the possible mechanism of the reaction was suggested.

引用

页码：58188 / 58202

页数：15

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