A novel tert-amino effect based approach to 1,2,3,4-tetrahydroquinoline-2-spirocycloalkanes

被引：20
|
作者：
Tverdokhlebov, Anton V.
Gorulya, Alexander P.
Tolmachev, Andrey A.
Kostyuk, Alexander N.
Chernega, Alexander N.
Rusanov, Eduard B.
机构：
[1] Enamine Ltd, UA-01103 Kiev, Ukraine
[2] Kiev Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine
[3] NAS, Inst Organ Chem, UA-02094 Kiev, Ukraine
来源：
TETRAHEDRON | 2006年 / 62卷 / 39期
关键词：
aldehydes; tert-amino effect; nitrites; quinoline; spiro compounds;
D O I：
10.1016/j.tet.2006.07.042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An interaction of 2-[cyclohexyl(methyl)amino]benzaldehydes with substituted acetonitriles X-CH2CN (X=CN, Tos, hetaryl) was found to yield 1-methyl-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3-carbonitriles. The corresponding spiroquinoline-2,1'-cyclopentane analogues were obtained similarly starting from 2-[cyclopentyl(methyl)amino]benzaldehydes. The reaction was assumed to proceed via initial Knoevenagel condensation and further ring closure of the formed adduct according to the tert-amino effect mechanism. The structure of the prepared compounds was confirmed unambiguously by X-ray crystallographic study. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：9146 / 9152
页数：7
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