Novel [4+2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates

被引：8

作者：

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

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

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

Kostyrko, E. O. ^{[2
]}

机构：

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

[2] AA Bogomolets Natl Med Univ, UA-010601 Kiev, Ukraine

来源：

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

关键词：

arylmethylidenemalononitriles; cyanoselenoacetamide; cyanothioacetamide; prop-2-ene-selenoamides; prop-2-enethioamides; 1,4,5,6-tetrahydropyridines; 4+2] cycloaddition; X-ray structural analysis; CONDENSED PYRIDINE-2(1H)-THIONES; UNEXPECTED PRODUCTS; CRYSTAL-STRUCTURE; NITRILES; CYANOTHIOACETAMIDE; 3-ARYL-2-CYANOTHIOACRYLAMIDES; MALONONITRILE; DERIVATIVES; CYCLIZATION; ALDEHYDES;

D O I：

10.1007/s10593-013-1378-y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of arylmethylidenemalononitriles with 3-aryl-2-cyanoprop-2-eneselenoamides in the presence of Et3N gave triethylammonium 4,6-diaryl-3,5,5-tricyano-1,4,5,6-tetrahydropyridine-2-selenolates. A similar reaction with cyclohexylidenecyanothioacetamide yields triethylammonium 4-aryl-1,5,5-tri-cyano-3-azaspiro[5.5]undec-1-ene-2-thiolate. Alkylation of the obtained selenolates and thiolates gives 6-(alkylseleno)-2,4-diaryl-1,4-dihydropyridine-3,3,5(2H)-tricarbonitriles and 4-(alkylthio)-2-aryl-3-aza- spiro[5.5]undec-4-ene-1,1,5-tricarbonitriles, respectivelly. The structure of 2,4-di(2-furyl)-6-{[2-(4-methylphenyl)-2-oxoethyl]seleno}-1,4-dihydropyridine-3,3,5(2H)-tricarbonitrile has been confirmed by the X-ray structural analysis.

引用

页码：1289 / 1300

页数：12

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