Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 24, Pages 4581-4584Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc00633g
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Funding
- Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India, New Delhi
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An unprecedented and efficient AgSbF6-catalyzed domino aza-annulation/Diels-Alder/aromatization cascade for the construction of carbazoles, dihydrocarbazoles and tetrahydrocarbazoles was achieved using 2-(but-3-en-1-yn-1-yl) anilines in the presence of suitable dienophiles. The reaction proceeds via the in situ generation of 2-vinyl indoles and their subsequent trapping by various dienophiles with concomitant aromatization. A series of symmetrical, unsymmetrical and base sensitive dienophiles provide the corresponding carbazoles under mild conditions in excellent yields with high regioselectivity.
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