Convenient approach to polyoxygenated dibenzo[: C, e] pyrrolo[1,2- a] azepines from donor-acceptor cyclopropanes

A short convenient approach to polyoxygenated tetrahydrodibenzo[c,e]pyrrolo[1,2-a]azepines from the donor-acceptor cyclopropanes was developed. A simple synthetic sequence involves: (a) cyclopropane ring opening with azide ion and Krapcho dealkoxycarbonylation; (b) azide-to-imine transformation followed by imine reduction; (c) the oxidative cyclization of 5-aryl-1-benzylpyrrolidin-2-ones, the key intermediates for this approach. © 2018 the Partner Organisations.

Авторы
Boichenko M.A. 1 , Ivanova O.A. 1 , Andreev I.A. 2 , Chagarovskiy A.O. 2 , Levina I.I. 3 , Rybakov V.B. 1 , Skvortsov D.A. 1 , Trushkov I.V. 2, 4
Журнал
Organic Chemistry Frontiers
Издательство
Royal Society of Chemistry
Номер выпуска
19
Язык
Английский
Страницы
2829-2834
Статус
Опубликовано
Ссылка
Внешняя ссылка
DOI
10.1039/C8QO00742J
Том
5
Год
2018
Организации
  • 1 Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow, 119991, Russian Federation
  • 2 Laboratory of Chemical Synthesis, Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow, 117997, Russian Federation
  • 3 N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygina 4, Moscow, 119334, Russian Federation
  • 4 Faculty of Science, RUDN University, Miklukho-Maklaya 6, Moscow, 117198, Russian Federation
Ключевые слова
Azepines; Azide ion; Cyclopropane ring opening; Donor-acceptor cyclopropanes; Krapcho dealkoxycarbonylation; Oxidative cyclization; Synthetic sequence; Propane
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