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Diversity‐Oriented Microwave‐Assisted Synthesis of the 3‐Benzazepine Framework
Author(s) -
Peshkov Vsevolod A.,
Pereshivko Olga P.,
Donets Pavel A.,
Mehta Vaibhav P.,
Van der Eycken Erik V.
Publication year - 2010
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.201000583
Subject(s) - benzazepine , benzazepines , chemistry , intramolecular force , alkyne , acetylene , aldehyde , amine gas treating , combinatorial chemistry , ring (chemistry) , coupling (piping) , microwave irradiation , stereochemistry , catalysis , organic chemistry , mechanical engineering , engineering
An efficient diversity‐oriented procedure for the two‐step synthesis of 3‐benzazepines is described. The Cu I ‐catalyzed three‐component coupling of an aldehyde, an alkyne and an amine (A 3 ‐coupling) provides the required propargylamines and assures the generation of diversity. The Pd‐catalyzed intramolecular acetylene hydroarylation reaction selectively creates the seven‐membered 3‐benzazepine framework with full control over the ring size and the geometry around the double bond. Microwave irradiation is demonstrated to be highly efficient in promoting both steps.