Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives

被引：8

作者：

Frolov, K. A. ^{[1
]}

Dotsenko, V. V. ^{[1
]}

Krivokolysko, S. G. ^{[1
]}

机构：

[1] Vladimir Dal East Ukrainian Natl Univ, ChemEx Lab, UA-91034 Lugansk, Ukraine

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2013年 / 49卷 / 09期

关键词：

cyanoselenoacetamide; 1,2-dihydropyridine-3-carboxylic acid; enaminodicarbonyl compounds; Meldrum's acid; selenoorganic compounds; Thorpe-Ziegler reaction; vinyl substitution; ENAMINONES; INHIBITORS; CHEMISTRY; PYRIDINES;

D O I：

10.1007/s10593-013-1379-x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of cyanoselenoacetamide with a 2-anilinomethylene derivative of Meldrum's acid (2 equiv. KOH, EtOH, 20A degrees C) gives the 5-cyano-6-hydroseleno-2-oxo-1,2-dihydropyridine-3-carboxylic acid dipotassium salt. The latter reacts with alkyl halides to yield 5-cyano-6-(R-methylseleno)-2-oxo-1,2-dihydropyridine-3-carboxylic acids. Treatment of cyanoselenoacetamide with 2-anilinomethyl derivatives of dimedone and 1,3-cyclohexanedione is accompanied by oxidation and gives 2,2'-di-selane-1,2-diylbis(5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles). The obtained diselanes undergo cleavage using alkyl halides in KOH to give 2-(R-methylseleno)-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles or selenopheno[2,3-b]quinolines as Thorpe-Ziegler cyclization products of the latter in low yields.

引用

页码：1301 / 1307

页数：7

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