Reactions of 5,6,7,8-tetrafluoro-4-hydroxy-2H-chromen-2-ones with methylamine

被引：1

作者：

Shcherbakov, K. V. ^{[1
]}

Burgart, Ya. V. ^{[1
]}

Saloutin, V. I. ^{[1
]}

机构：

[1] Russian Acad Sci, Postovskii Inst Organ Synth, Ural Div, Ekaterinburg 620219, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 42卷 / 12期

基金：

俄罗斯基础研究基金会;

关键词：

Coumarin; Fluorine Atom; Methylamine; Methylammonium; Pyran Ring;

D O I：

10.1134/S107042800612013X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5,6,7,8-Tetrafluoro-4-hydroxy-2H-chromen-2-one reacts with methylamine to give methylammonium 5,6,7,8-tetrafluoro-2-oxo-2H-chromen-4-olate, regardless of the solvent. The reaction of 3-acetyl-5,6,7,8-tetrafluoro-4-hydroxy-2H-chromen-2-one with the same amine in ethanol or acetonitrile leads to the formation of methylammonium 3-acetyl-5,6,7,8-tetrafluoro-2-oxo-2H-chromen-4-olate, while in dimethyl sulfoxide 5,6,8-trifluoro-7-methylamino-3-(1-methylaminoethylidene)-3,4-dihydro-2H-chromene-2,4-dione is formed. The latter is also formed in the reaction of 5,6,7,8-tetrafluoro-4-hydroxy-3-(1-iminoethyl)-2H-chromen-2-one with methylamine in DMSO, whereas in ethanol and acetonitrile 5,6,7,8-tetrafluoro-3-(1-methylaminoethylidene)-3,4-dihydro-2H-chromene-2,4-dione is obtained. 5,6,7,8-Tetrafluoro-3-(1-methylaminoethylidene)3,4-dihydro-2H-chromene-2,4-dione reacts with methylamine, yielding 7-mono- or 5,7-bis(methylamino)-substituted derivatives.

引用

页码：1838 / 1844

页数：7

共 50 条

[1] Reactions of 5,6,7,8-Tetrafluoro-4-hydroxy-2H-chromen-2-ones with methylamine
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Ya. V. Burgart
V. I. Saloutin
[J]. Russian Journal of Organic Chemistry, 2006, 42 : 1838 - 1844
[2] Reactions of ethyl 5,6,7,8-tetrafluoro-2-methylchromone-3-carboxylate and 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin with S-nucleophiles
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