Oxidation reactions of azines: XIII. Synthesis, molecular structure, and oxidation reactions of 3-methyl-3,3,4,4,5,6-hexahydro-1H,2H-spiro[benzo[f]isoquinoline-1,2-naphthalen]-1-one

The condensation of 3,4-dihydronaphthalen-1(2H)-one with methylamine and formaldehyde in acid medium gave N,N-bis(1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylmethyl)methanamine hydrochloride which was converted into 3-methyl-3,3,4,4,5,6-hexahydro-1H,2H-spiro[benzo[f]isoquinoline-1,2-naphthalen]-1-one by heating in 48% aqueous HBr or 50% H2SO4. Oxidation of the spiro compound with KMnO4 initially involved the methylene group of the allylamine fragment with formation of the corresponding lactam which then underwent cis-dihydroxylation at C4a and C10b. Oxidation of the same compound with KMnO4 in the presence of some CH acids (trifluoroacetone and 4-bromoacetophenone) or aromatic amines (4-fluoroaniline and 2-bromo-4-nitroaniline) afforded, respectively, 4-acylmethylidene or 4-arylimino derivatives via C-C or C-N cross-coupling at the 4-position. © 2014 Pleiades Publishing, Ltd.

Редакторы
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Издательство
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Номер выпуска
12
Язык
Английский
Страницы
1797-1803
Статус
Опубликовано
Подразделение
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Номер
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Том
50
Год
2014
Организации
  • 1 Peoples' Friendship University of Russia, ul. Miklukho-Maklaya 6, Moscow, 117198, Russian Federation
  • 2 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russian Federation
Ключевые слова
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Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/5029/