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Synthesis 2002(13): 1912-1916
DOI: 10.1055/s-2002-33908
DOI: 10.1055/s-2002-33908
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Synthesis of 2,4-Substituted [1,8]Naphthyridines from 3-(2-Amino-5-methylpyridin-3-yl)-1-arylprop-2-yn-1-ones
Weitere Informationen
Received
2 May 2002
Publikationsdatum:
09. September 2002 (online)
Publikationsverlauf
Publikationsdatum:
09. September 2002 (online)
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
- 1
Infectious
Disease and Therapy, The New Generation of Quinolones
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References
When the reaction was carried out under 1 atm of CO, 2a was obtained in 46% yield.