A Straightforward Approach to Tetrahydroindolo[3,2-b]carbazoles and 1-Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole-Derived Cyclopropanes

Olga A Ivanova; Ekaterina M Budynina; Victor N Khrustalev; Dmitriy A Skvortsov; Igor V Trushkov; Mikhail Ya Melnikov

doi:10.1002/chem.201502287

A Straightforward Approach to Tetrahydroindolo[3,2-b]carbazoles and 1-Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole-Derived Cyclopropanes

Chemistry. 2016 Jan 22;22(4):1223-7. doi: 10.1002/chem.201502287. Epub 2015 Aug 6.

Authors

Olga A Ivanova¹, Ekaterina M Budynina^{2

3}, Victor N Khrustalev^{4

5}, Dmitriy A Skvortsov¹, Igor V Trushkov^{1

6}, Mikhail Ya Melnikov¹

Affiliations

¹ Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991, (Russian Federation).
² Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991, (Russian Federation). ekatbud@kinet.chem.msu.ru.
³ Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology and Immunology named after Dmitry Rogachev, Samory Mashela 1, Moscow, 117997, (Russian Federation). ekatbud@kinet.chem.msu.ru.
⁴ A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova 28, Moscow, 119991, (Russian Federation).
⁵ Peoples' Friendship University of Russia, Miklukho-Maklaya 6, Moscow, 117198, (Russian Federation).
⁶ Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology and Immunology named after Dmitry Rogachev, Samory Mashela 1, Moscow, 117997, (Russian Federation).

PMID: 26251074
DOI: 10.1002/chem.201502287

Abstract

A rapid new approach to produce biologically relevant bisindoles, namely indolyltetrahydrocarbazoles and indolo[3,2-b]carbazoles, has been developed, based on the Ga(OTf)3 -catalyzed [3+3] cyclodimerization of indole-derived donor-acceptor cyclopropanes. Chemoselectivity of the process depends on the location of the three-membered ring at the indole core.

Keywords: Lewis acids; cyclopropanes; dimerization; domino reactions; indoles.

Publication types

Research Support, Non-U.S. Gov't