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Palladium‐Catalyzed Regioselective Synthesis of 1‐Benzoazepine Carbonitriles from o ‐Alkynylanilines via 7‐ endo ‐dig Annulation and Cyanation
Author(s) -
Dhandabani Ganesh Kumar,
Mutra Mohana Reddy,
Wang JehJeng
Publication year - 2018
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.201800865
Subject(s) - cyanation , chemistry , annulation , palladium , regioselectivity , trimethylsilyl cyanide , substrate (aquarium) , catalysis , trimethylsilyl , cyanide , combinatorial chemistry , organic chemistry , medicinal chemistry , geology , oceanography
We herein report a three‐component, one‐pot cascade reaction involving an imination/annulation/cyanation sequence for the synthesis of 1‐benzoazepine carbonitrile derivatives using readily available o ‐alkynylanilines, cyclic ketones and trimethylsilyl cyanide. This regio‐ and stereoselective reaction was achieved by combining palladium(II) trifluoroacetate and copper(II) acetate in dimethyl sulfoxide. The important features of this method include a broad substrate scope, the use of trimethylsilyl cyanide as a cyanating agent, the formation of two C−C bonds and one C−N bond, mild reaction conditions and good product yields.