Studies on the Reaction of Cycloalkanones with Malonodinitrile

被引：6

作者：

Abdelrazek, Fathy M. ^{[1
]}

Metwally, Nadia H. ^{[1
]}

Kassab, Nazmi A. ^{[1
]}

Jaafar, Mohammed T. ^{[1
]}

Metz, Peter ^{[2
]}

Jaeger, Anne ^{[2
]}

机构：

[1] Cairo Univ, Dept Chem, Fac Sci, Giza 12613, Egypt

[2] Tech Univ Dresden, Inst Organ Chem, D-01069 Dresden, Germany

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2014年 / 51卷 / 06期

关键词：

ABSORPTION SPECTRAL PROPERTIES; MOLLUSCICIDAL ACTIVITY; ETHYL BENZOYLACETATE; MALONONITRILE; PYRIDAZINE;

D O I：

10.1002/jhet.1883

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopentanone reacts with malononitrile catalyzed by piperidine or sodium acetate to afford under any case cyclopentylidenemalononitrile dimer: 5-aminospiro-[2,6,7,7a-tetrahydroindene-7,1-cyclopentane]-4,6,6-tricarbonitrile (7) as the sole product. Contrary to this behavior, cyclohexanone reacts with malononitrile catalyzed by piperidine to afford the analogous cyclohexylidenemalononitrile dimer: 2-aminospiro-[3,4,5,6,7,4a-hexahydronaphthalene-4,1-cyclohexane]-1,3,3-tricarbonitrile (11); whereas when the reaction is catalyzed by sodium acetate, it afforded 9,10-diaza-8,11-dioxo-tricyclo-[4.3.3.0(1,6)]-dodecane-7,12-dicarbonitrile (12). The structures of these products were established on the basis of their elemental analysis and spectral data, and plausible mechanism has been postulated to account for their formation. X-ray crystallography was carried out as a further evidence for structures7 and 12.

引用

页码：1785 / 1790

页数：6

共 25 条

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