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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Bibliographic Details
Published in:Russian journal of organic chemistry Vol. 52; no. 10; pp. 1444 - 1451
Main Authors: Savel’ev, V. A., Tikhonov, A. Ya, Rybalova, T. V.
Format: Journal Article
Language:English
Published: Moscow Pleiades Publishing 01.10.2016
Springer Nature
Springer Nature B.V
Subjects:
Amides
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Diazomethane
Esters
Organic Chemistry
Oximes
Physical Sciences
Science & Technology
FRAGMENTATION
DERIVATIVES
ISSN:1070-4280, 1608-3393
Online Access:Get full text
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Summary: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.
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ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428016100134