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
收藏
页码：661 / 669
页数：9
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