Reactivity of 5-endo-Hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-en-3-ones and Their Isomerization Initiated by Acids and Bases

被引：0

作者：

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

Tarabara, I. N. ^{[2
]}

Omel'chenko, I. V. ^{[3
]}

Pal'chikov, V. A. ^{[2
,4
]}

机构：

[1] R&D Enterprise Enamine Ltd, Kiev, Ukraine

[2] Oles Honchar Dnepropetrovsk Natl Univ, Pr Gagarina 72, UA-49010 Dnepropetrovsk, Ukraine

[3] Natl Acad Sci Ukraine, Inst Single Crystals, State Sci Inst, Kharkov, Ukraine

[4] Peoples Friendship Univ Russia, Moscow, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 52卷 / 05期

关键词：

N-ACYLIMINIUM IONS; ASYMMETRIC-SYNTHESIS; CAGE COMPOUNDS; DERIVATIVES;

D O I：

10.1134/S1070428016050080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Study of isomerization of 5-endo-hydroxy-4-azatricyclo[5.2.1.0(2,6)]dec-8-en-3-ones under the action of Lewis acids (MgBr2, AlCl3), CF3COOH, and NaH showed that the optimum catalyst of the process was trifluoroacetic acid. In reaction of 4-benzyl-5-endo-hydroxy-4-azatricyclo-[5.2.1.0(2,6)]dec-8-en-3-one with anhydrous AlCl3 in benzene was unexpectedly isolated N-benzyl-3-(diphenylmethyl)bicyclo[2.2.1]hept-5-ene-2-carboxamide. A convenient method was developed for the preparation of 5-exo-alkoxy-4-alkyl(aryl)-4-azatricyclo[5.2.1.0(2,6)]dec-8-en-3-ones.

引用

页码：661 / 669

页数：9

共 39 条

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[25] Effect of the halide Counterion in the ROMP of exo-benzyl-[2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) ethyl] dimethyl ammonium bromide/chloride
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