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Synthesis of Azocino[5,4‐ b ]indoles via Gold‐Catalyzed Intramolecular Alkyne Hydroarylation
Author(s) -
Peshkov Vsevolod A.,
Pereshivko Olga P.,
Eycken Erik V. Van der
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200305
Subject(s) - chemistry , alkyne , intramolecular force , trifluoromethanesulfonate , indole test , tryptamines , catalysis , cationic polymerization , combinatorial chemistry , substrate (aquarium) , medicinal chemistry , organic chemistry , stereochemistry , tryptamine , biochemistry , oceanography , geology
An efficient procedure for the synthesis of the azocino[5,4‐ b ]indole framework is presented, relying on a cationic gold‐catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3‐substituted 2‐propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior to our previously described mercury(II) triflate catalyst, and hence the substrate scope of the process was significantly expanded.