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

Org Biomol Chem. 2015 Mar 28;13(12):3732-41. doi: 10.1039/c4ob02641a.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Aldehydes / chemistry*
  • Berberine / chemical synthesis
  • Berberine / chemistry*
  • Berberine Alkaloids / chemical synthesis
  • Berberine Alkaloids / chemistry*
  • Catalysis
  • Isoquinolines / chemistry*
  • Ketones / chemistry*
  • Silver / chemistry*
  • Temperature*

Substances

  • Acetates
  • Aldehydes
  • Berberine Alkaloids
  • Isoquinolines
  • Ketones
  • Berberine
  • Silver
  • palmatine
  • isoquinoline
  • ammonium acetate