- 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
PMID25687222
RESUMEN
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.
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Sigma-Aldrich
Cloroformo-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS
Sigma-Aldrich
Cloroformo-d, "100%", 99.96 atom % D, contains 0.5 wt. % silver wire as stabilizer