A Straightforward Approach to Tetrahydroindolo[3, 2‐b]carbazoles and 1‐Indolyltetrahydrocarbazoles through [3+3] Cyclodimerization of Indole‐Derived Cyclopropanes. Issue 4 (6th August 2015)

• Record Type: Journal Article
• Authors: Ivanova, Olga A.; Budynina, Ekaterina M.; Khrustalev, Victor N.; Skvortsov, Dmitriy A.; Trushkov, Igor V.; Melnikov, Mikhail Ya.
• Is Part Of: Chemistry. Volume 22:Issue 4(2016)
• Page Start: 1223
• Page End: 1227
• Publication Date: 2015-08-06
• Subjects: cyclopropanes -- dimerization -- domino reactions -- indoles -- Lewis acids; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201502287
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Gemination for creation : A new method for bisindole assembly was proposed through [3+3] cyclodimerization of indole‐derived cyclopropanes. Variations in the cyclopropane position at the indole core fine‐tune the process towards the selective formation of indolyltetrahydrocarbazoles or indolo[3, 2‐ b ]carbazoles.