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From PtCl 2 ‐ and Acid‐Catalyzed to Uncatalyzed Cycloisomerization of 2‐Propargyl Anilines: Access to Functionalized Indoles
Author(s) -
Cariou Kevin,
Ronan Baptiste,
Mignani Serge,
Fensterbank Louis,
Malacria Max
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200604026
Subject(s) - cycloisomerization , moiety , indole test , propargyl , alkyne , chemistry , catalysis , electrophile , medicinal chemistry , nitrogen atom , combinatorial chemistry , stereochemistry , organic chemistry , group (periodic table)
On the move : PtCl 2 ‐catalyzed electrophilic activation of an alkyne moiety triggers a heterocyclization accompanied by migrations of both an allyl group and an acetate group to produce an indole (see scheme). Variation of the reaction conditions (particularly the temperature) as well as substituents at the propargylic position and on the nitrogen atom allows easy and versatile access to a myriad of indole substrates.