An Efficient Synthesis of 2,4-Substituted [1,8]Naphthyridines from 3-(2-Amino-5-methylpyridin-3-yl)-1-arylprop-2-yn-1-ones

Giorgio  Abbiati; Antonio  Arcadi; Fabio  Marinelli; Elisabetta  Rossi

doi:10.1055/s-2002-33908

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Synthesis 2002(13): 1912-1916
DOI: 10.1055/s-2002-33908

PAPER

An Efficient Synthesis of 2,4-Substituted [1,8]Naphthyridines from 3-(2-Amino-5-methylpyridin-3-yl)-1-arylprop-2-yn-1-ones

Giorgio Abbiati^a, Antonio Arcadi^b, Fabio Marinelli*^b, Elisabetta Rossi^a
^a Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy
^b Dipartimento di Chimica Ingegneria Chimica e Materiali della Facoltà di Scienze, Università di L’Aquila, Via Vetoio, Coppito Due, 67100 L’Aquila, Italy
Fax: +39(862)433753; e-Mail: fmarinel@univaq.it;

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Publication History

Received 2 May 2002
Publication Date:
09 September 2002 (online)

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Abstract

3-(2-Amino-5-methylpyridin-3-yl)-1-arylprop-2-yn-1-ones 2, readily available through Pd-catalyzed carbonylative coupling of 5-methyl-3-[2-(trimethylsilyl)ethynyl]pyridine-2-ylamine (1) with aryl iodides in the presence of carbon monoxide, undergo a domino conjugate addition/annulation reaction to give 4-heterosubstituted 2-aryl[1,8]naphthyridines 3 in high yields.

Key words

[1,8]naphthyridines - nucleophilic addition - α,β-ynones - palladium - diphenylphosphane

References

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When the reaction was carried out under 1 atm of CO, 2a was obtained in 46% yield.