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Gold-Catalyzed Intramolecular Alkyne Cycloisomerization Cascade: Direct Synthesis of Aryl-Annulated[a]carbazoles from Aniline-Substituted Diethynylarenes
Article first published online: 9 FEB 2010
DOI: 10.1002/adsc.200900880
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Hirano, K., Inaba, Y., Watanabe, T., Oishi, S., Fujii, N. and Ohno, H. (2010), Gold-Catalyzed Intramolecular Alkyne Cycloisomerization Cascade: Direct Synthesis of Aryl-Annulated[a]carbazoles from Aniline-Substituted Diethynylarenes. Adv. Synth. Catal., 352: 368–372. doi: 10.1002/adsc.200900880
Publication History
- Issue published online: 17 FEB 2010
- Article first published online: 9 FEB 2010
- Manuscript Received: 18 DEC 2009
Funded by
- Kaken Pharmaceutical Co., Ltd.
- Grant-in-Aid for Encouragement of Young Scientists (A)
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- Targeted Proteins Research Program
- Program for Promotion of Fundamental Studies in Health Sciences of the National Institute of Biomedical Innovation (NIBIO)
- Research Fellowships of the Japan Society for the Promotion of Science (JSPS) for Young Scientists
Keywords:
- alkynes;
- carbazoles;
- cascade reactions;
- gold catalysis;
- heterocycle synthesis
Abstract
Aniline-substituted diethynylarenes, which are readily synthesized through Sonogashira coupling reactions from commercially available 1,2-dihaloarenes, directly produce aryl- and heteroaryl-annulated[a]carbazoles by the gold-catalyzed intramolecular cascade hydroamination/cycloisomerization without producing theoretical by-products. This new atom-economical route is easily applicable to various aryl-annulated[a]carbazoles containing an alkyl, aryl or ester substituent.