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One‐Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides
Author(s) -
Rajasekar Shanmugam,
Yadagiri Dongari,
Anbarasan Pazhamalai
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502201
Subject(s) - sulfonyl , chemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , alkyl
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 α‐iminocarbenes onto the C3H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH 3 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‐β‐carboline and tryptoline.