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Superacidic Activation of 1- and 3-Isoquinolinols and Their Electrophilic Reactions Научная публикация

Журнал Journal of Organic Chemistry
ISSN: 0022-3263 , E-ISSN: 1520-6904
Вых. Данные Год: 2002, Том: 67, Номер: 25, Страницы: 8943-8951 Страниц : 9 DOI: 10.1021/jo0204855
Ключевые слова Aluminum compounds; Catalysis; Hydrogenation; Isomers
Авторы Koltunov Konstantin Yu. 1 , Prakash G.K.Surya 1 , Rasul Golam 1 , Olah George A. 1
Организации
1 Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California,University Park, Los Angeles, California 90089-1661

Реферат: Isomeric 1- and 3-isoquinolinols (11 and 12) when activated in CF3SO3H−SbF5 acid system undergo selective ionic hydrogenation with cyclohexane to give 5,6,7,8-tetrahydro-1(2H)- and 5,6,7,8-tetrahydro-3(2H)-isoquinolinones (22 and 27). Under the influence of aluminum chloride similar products were also obtained along with 3,4-dihydro-1(2H)- and 1,4-dihydro-3(2H)-isoquinolinones (23 and 28), respectively. Compounds 11 and 12 also condense with benzene in the presence of aluminum halides, under mild conditions, to give 3,4-dihydro-3-phenyl-1(2H)- and 1,4-dihydro-1-phenyl-3(2H)-isoquinolinones (24 and 29), respectively. Prolonged reaction time or catalysis under strongly acidic HBr−AlBr3 provides an alternative reaction pathway to yield 5,6-dihydro-6,8-diphenyl-1(2H)- and 5,6,7,8-tetrahydro-6,8-diphenyl-3(2H)-isoquinolinones (25 and 30), respectively. Products 24 and 29 were also found to revert back to 11 and 12 in the presence of aluminum halides in o-dichlorobenzene. The mechanism of these intriguing reactions, which involves superelectrophilic dicationic intermediates, is discussed.
Библиографическая ссылка: Koltunov K.Y. , Prakash G.K.S. , Rasul G. , Olah G.A.
Superacidic Activation of 1- and 3-Isoquinolinols and Their Electrophilic Reactions
Journal of Organic Chemistry. 2002. V.67. N25. P.8943-8951. DOI: 10.1021/jo0204855 WOS Scopus РИНЦ CAPlusCA OpenAlex
Даты:
Поступила в редакцию: 22 июл. 2002 г.
Опубликована online: 19 нояб. 2002 г.
Опубликована в печати: 1 дек. 2002 г.
Идентификаторы БД:
Web of science: WOS:000179736300032
Scopus: 2-s2.0-0037073928
РИНЦ: 14382403
Chemical Abstracts: 2002:874018
Chemical Abstracts (print): 138:122315
OpenAlex: W2040101282
Цитирование в БД:
БД Цитирований
Web of science 45
Scopus 46
OpenAlex 41
Альметрики: