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  • 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
RESUMO

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
Dimetilsulfóxido-d6, 99.9 atom % D
Sigma-Aldrich
Clorofórmio-d, 99.8 atom % D
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Sigma-Aldrich
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