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

Literature Information

Publication Date 2018-08-30
DOI 10.1039/C8QO00742J
Impact Factor 5.281
Authors

Maksim A. Boichenko, Olga A. Ivanova, Ivan A. Andreev, Alexey O. Chagarovskiy, Irina I. Levina, Victor B. Rybakov, Dmitriy A. Skvortsov


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Abstract

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.

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