Formation of ω-(4-oxo-1,4-dihydropyridin-2-yl)alkanamides in the Beckmann rearrangement of spiro-fused cycloalkanone oximes

ω-(4-Oxo-1,4-dihydropyridin-2-yl)alkanamides were obtained from cycloalkanone oximes spirofused to 4-oxo-6-methyl-1,2,3,4-tetrahydropyridine fragment through the α-carbon atom and C 2 , respectively, on heating in polyphosphoric acid. The resulting amides were converted to the corresponding acids an...

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Vydáno v:Russian journal of organic chemistry Ročník 52; číslo 10; s. 1444 - 1451
Hlavní autoři: Savel’ev, V. A., Tikhonov, A. Ya, Rybalova, T. V.
Médium: Journal Article
Jazyk:angličtina
Vydáno: Moscow Pleiades Publishing 01.10.2016
Springer Nature
Springer Nature B.V
Témata:
Amides
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Diazomethane
Esters
Organic Chemistry
Oximes
Physical Sciences
Science & Technology
FRAGMENTATION
DERIVATIVES
ISSN:1070-4280, 1608-3393
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Shrnutí:ω-(4-Oxo-1,4-dihydropyridin-2-yl)alkanamides were obtained from cycloalkanone oximes spirofused to 4-oxo-6-methyl-1,2,3,4-tetrahydropyridine fragment through the α-carbon atom and C 2 , respectively, on heating in polyphosphoric acid. The resulting amides were converted to the corresponding acids and methyl esters. Methylation of 5-(6-methyl-4-oxo-1,4-dihydropyridin-2-yl)pentanamide with diazomethane gave 4-methoxypyridine derivative as the major product and a small amount of N -methyl derivative, 5-(1,6-di-methyl- 4-oxo-1,4-dihydropyridin-2-yl)pentanamide.
Bibliografie:ObjectType-Article-1
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ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428016100134