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.

Authors
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
Journal
Organic Chemistry Frontiers
Publisher
Royal Society of Chemistry
Number of issue
19
Language
English
Pages
2829-2834
Status
Published
Link
External link
DOI
10.1039/c8qo00742j
Volume
5
Year
2018
Organizations
  • 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
Keywords
Azepines; Azide ion; Cyclopropane ring opening; Donor-acceptor cyclopropanes; Krapcho dealkoxycarbonylation; Oxidative cyclization; Synthetic sequence; Propane
Date of creation
19.10.2018
Date of change
28.09.2021
Short link
https://repository.rudn.ru/en/records/article/record/6400/
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