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 |
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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 |
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Организации |
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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
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
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 |