Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene,...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2010-12, Vol.46 (12), p.1830-1834
Main Authors: Sagitullina, G. P, Vorontsova, M. A, Garkushenko, A. K, Poendaev, N. V, Sagitullin, R. S
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene, prop-2-ynyl alcohol, and 2-methylbut-3-yn-2-ol, respectively, gave 2-ethynyl-5-nitropyridine. The hydration of 2-ethynyl-5-nitropyridine and 5-nitro-2-(phenylethynyl)pyridine according to Kucherov afforded 2-acetyl-5-nitropyridine and 5-nitro-2-phenacylpyridine, respectively.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428010120109