Novel 2,4-methanoadamantane-benzazepine by domino photochemistry of N-(1-adamantyl)phthalimide.
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.
Basarić
Nikola
N
Department of Organic Chemistry and Biochemistry, Ruder Bosković Institute, 10 000 Zagreb, Croatia. nbasaric@irb.hr
Horvat
Margareta
M
Mlinarić-Majerski
Kata
K
Zimmermann
Elmar
E
Neudörfl
Jörg
J
Griesbeck
Axel G
AG
D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001552:Benzazepines / Q000737:chemistry*; D006868:Hydrolysis; D010777:Photochemistry; D010797:Phthalimides / Q000737:chemistry*
C532595:2,4-methanoadamantane-benzazepine; D000596:Amino Acids; D001552:Benzazepines; D010797:Phthalimides; D000218:Adamantane