Novel 2,4-methanoadamantane-benzazepine by domino photochemistry of N-(1-adamantyl)phthalimide

被引：29

作者：

Basaric, Nikola ^{[1
]}

Horvat, Margareta ^{[1
]}

Mlinaric-Majerski, Kata ^{[1
]}

Zimmermann, Elmar ^{[2
]}

Neudoerfl, Joerg ^{[2
]}

Griesbeck, Axel G. ^{[2
]}

机构：

[1] Rudjer Boskovic Inst, Dept Organ Chem & Biochem, Zagreb 10000, Croatia

[2] Univ Cologne, Dept Chem, D-50939 Cologne, Germany

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 18期

关键词：

D O I：

10.1021/ol801362x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photochemical reaction of N-(1-adamantyl)phthalimide (1) gives cleanly one product, the novel hexacyclic benzazepine derivative of 2,4-methanoadamantane 2. Its structure was characterized by spectroscopic methods and X-ray analysis and represent the first example of the 2-azahexacyclo[8.7.1.1(1,4).0(4,9).0(11,16).0(12,18)]nonadeca-4,6,8-triene skeleton. The product is formed by a domino process of two consecutive excited-state intramolecular gamma-hydrogen-transfer reactions. Base hydrolysis of the benzazepine 2 gives in high yield the keto derivative of the 1,2-substituted adamantane epsilon-amino acid 3.

引用

页码：3965 / 3968

页数：4

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