Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 47, Pages 17079-17084Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502201
Keywords
aminoethylation; indoles; rhodium; triazoles; tryptamine
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Funding
- Department of Science and Technology (DST), New Delhi, India [SR/S1/OC-48/2012]
- Council of Scientific and Industrial Research (CSIR)
- Indian Institute of Technology Madras (IITM)
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A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of a-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-beta-carboline and tryptoline.
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