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Novel five‐membered ring formation by oxidative photocyclization of 4‐(2‐arylvinyl)benzo[ a ]quinolizinium salts
Author(s) -
Arai Sadao,
Yoda Hiroe,
Sato Kiyoshi,
Yamagishi Takamichi
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390230
Subject(s) - chemistry , substituent , ring (chemistry) , yield (engineering) , salt (chemistry) , medicinal chemistry , derivative (finance) , aryl , stereochemistry , organic chemistry , alkyl , materials science , economics , financial economics , metallurgy
Oxidative photocyclization of 4‐(2‐arylvinyl)benzo[ a ]quinolizinium salts ( 6 ) gave five‐ or six‐mem‐bered rings depending on the aryl substituent. The olefins 6a and 6b with a phenyl or naphthyl substituent resulted in a normal six‐membered ring formation to afford 6a‐azoniapicene and 6a‐azoniabenzo[ b ]picene salts ( 7 and 8 ), respectively. In contrast, the photo‐reaction of pyridyl substituted derivative 6c resulted in novel five‐membered ring formation to yield 3b‐azonia‐5‐(2‐pyridyl)acephenanthrylene salt ( 10 ).