Synthesis and molecular structure of 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives and dimethyl 4-cyano-2,3,6,7-tetrahydro-1H-3-benzazonine-5,6- dicarboxylate

A study was carried out on the direction of 1,2,3,4- tetrahydroisoquinolinium quaternary salt rearrangements by the action of base with or without dimethyl acetylenedicarboxylate. These quaternary salts containing a methylene group at the nitrogen atom, are converted in the presence of base through intermediate N-ylides into the Stevens rearrangement products, namely, tetrahydro-3-benzazepines. Upon the addition of dimethyl acetylenedicarboxylate as an electrophilic trap, this diester adds at the carbanion site of the ylide with subsequent recyclization of the piperidine fragment to give a 2-benzazonine derivative with an unusual 4,5-positioning of the olefin bond in the nine-membered heterocycle. An X-ray structural analysis established the molecular structures of 2-cyano-3-methyl-2,3,4,5-tetrahydro-1H- 3-benzazepine and dimethyl 4-cyano-2,3,6,7-tetrahydro-1H-3-benzazo-nine-5,6- dicarboxylate. © 2012 Springer Science+Business Media New York.

Авторы
Soldatenkov A.T. 1 , Soldatova S.A. 1 , Mamyrbekova-Bekro J.A.2 , Gimranova G.S. 1 , Malkova A.V. 1 , Polyanskii K.B. 1 , Kolyadina N.M. 1 , Khrustalev V.N.3
Редакторы
-
Издательство
Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau
Номер выпуска
9
Язык
Английский
Страницы
1332-1339
Статус
Опубликовано
Подразделение
-
Номер
-
Том
48
Год
2012
Организации
  • 1 Peoples Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
  • 2 University of Abobo-Ajamé, 02 BP801, Abidjan, Cote d'Ivoire
  • 3 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 117813, Russian Federation
Ключевые слова
2,3,6,7-tetrahydro-1H-3-benzazonine-5,6- dicarboxylate; quaternary 1,2,3,4-tetrahydroisoquinolinium salts; sigmatropic rearrangement; tetrahydro-3-benzazepines
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/2225/