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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
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.

MATERIALI
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Descrizione del prodotto

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