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Nitrogenated Azaphilone Derivatives through a Silver‐Catalysed Reaction of Imines from ortho ‐Alkynylbenzaldehydes
Author(s) -
Fernández Patricia,
Fañanás Francisco J.,
Rodríguez Félix
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700170
Subject(s) - nucleophile , electrophile , combinatorial chemistry , catalysis , molecule , chemistry , coupling (piping) , cascade , simple (philosophy) , computational chemistry , materials science , organic chemistry , philosophy , epistemology , chromatography , metallurgy
Nitrogenated azaphilones are interesting natural products with a wide range of applications. The structure of these compounds is characterized by the presence of an isoquinolinone framework. Here, we describe a new multicomponent silver‐catalysed reaction that allows the transformation of simple imines derived from ortho ‐alkynylbenzaldehydes into complex nitrogenated azaphilone‐type molecules in a straightforward way. This atom‐economical process is high yielding, technically very simple and proceeds through a series of cascade processes that imply cycloisomerisation and formal cross‐coupling reactions. This conceptually new process formally involves the synchronised catalytic generation and selective coupling of a nucleophile (isoquinolinone) and an electrophile (isoquinolinium). Some interesting colour properties of the synthesized azaphilone‐type molecules are discussed.