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Acylative Coupling of Amine and Indole Using Chloroform as a Carbonyl Group
Author(s) -
Nishida Yuika,
Takeda Norihiko,
Matsuno Kenji,
Miyata Okiko,
Ueda Masafumi
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800571
Subject(s) - chemistry , chloroform , phosgene , acylation , intramolecular force , indole test , amine gas treating , organic chemistry , dimethylzinc , combinatorial chemistry , medicinal chemistry , catalysis
Chloroform‐mediated acylative coupling of amines with indoles has been developed. When indoles and amines in chloroform were treated with dimethylzinc in the presence of air, the three‐component aminocarbonylation reaction proceeded via in‐situ generation of phosgene from chloroform and O 2 to provide indole‐3‐carboxamides in a single operation. Application to the synthesis of biologically active compounds and intramolecular acylation are also described.