Accéder au contenu
Merck
  • 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.

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.

Organic & biomolecular chemistry (2015-02-18)
Virsinha Reddy, Abhijeet S Jadhav, Ramasamy Vijaya Anand
RÉSUMÉ

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.

MATÉRIAUX
Référence du produit
Marque
Description du produit

Sigma-Aldrich
Sulfoxyde de diméthyle-d6, Diméthylsulfoxyde-d6, 99.9 atom % D
Sigma-Aldrich
Chloroforme-d, 99.8 atom % D
Sigma-Aldrich
Sulfoxyde de diméthyle-d6, Diméthylsulfoxyde-d6, 99.9 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroforme-d, 99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Sulfoxyde de diméthyle-d6, Diméthylsulfoxyde-d6, 99.5 atom % D
Sigma-Aldrich
Chloroforme-d, 99.8 atom % D, contains 0.05 % (v/v) TMS
Sigma-Aldrich
Sulfoxyde de diméthyle-d6, Diméthylsulfoxyde-d6, "100%", 99.96 atom % D
Sigma-Aldrich
Chloroforme-d, 99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Chloroforme-d, 99.8 atom % D, contains 0.1 % (v/v) TMS
Sigma-Aldrich
Sulfoxyde de diméthyle-d6, Diméthylsulfoxyde-d6, anhydrous, 99.9 atom % D
Sigma-Aldrich
Sulfoxyde de diméthyle-d6, Diméthylsulfoxyde-d6, 99.9 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Chloroforme-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroforme-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer
Sigma-Aldrich
Chloroforme-d, "100%", 99.95 atom % D
Sigma-Aldrich
Chloroforme-d, ≥99.8 atom % D, anhydrous
Sigma-Aldrich
Chloroforme-d, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Sulfoxyde de diméthyle-d6, Diméthylsulfoxyde-d6, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Sulfoxyde de diméthyle-d6, Diméthylsulfoxyde-d6, "Special HOH", ≥99.9 atom % D
Sigma-Aldrich
Chloroforme-d, "100%", 99.96 atom % D, contains 0.5 wt. % silver wire as stabilizer