期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 13, 页码 3002-3006出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201700170
关键词
azaphilones; cascade reactions; homogeneous catalysis; natural product analogues; silver
资金
- MINECO-Spain [CTQ2013-41336-P]
- FICYT of Principado de Asturias
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 azaphilonetype 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.
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