Issue 12, 2015

A room-temperature protocol to access isoquinolines through Ag(i) catalysed annulation of o-(1-alkynyl)arylaldehydes and ketones with NH4OAc: elaboration to berberine and palmatine

Abstract

An efficient and mild protocol for the direct construction of aryl- and alkyl-substituted isoquinolines has been realized through silver nitrate catalyzed aromatic annulation of o-(1-alkynyl)arylaldehydes and ketones with ammonium acetate. The salient feature of this methodology is that this annulation could be effected at room temperature leading to a wide range of isoquinoline derivatives in good to excellent yields. Additionally, this approach has been employed to the synthesis of biologically important isoquinoline alkaloids such as berberine and palmatine.

Graphical abstract: A room-temperature protocol to access isoquinolines through Ag(i) catalysed annulation of o-(1-alkynyl)arylaldehydes and ketones with NH4OAc: elaboration to berberine and palmatine

Supplementary files

Article information

Article type
Paper
Submitted
21 Dec 2014
Accepted
09 Feb 2015
First published
09 Feb 2015

Org. Biomol. Chem., 2015,13, 3732-3741

A room-temperature protocol to access isoquinolines through Ag(I) catalysed annulation of o-(1-alkynyl)arylaldehydes and ketones with NH4OAc: elaboration to berberine and palmatine

V. Reddy, A. S. Jadhav and R. Vijaya Anand, Org. Biomol. Chem., 2015, 13, 3732 DOI: 10.1039/C4OB02641A

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