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

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

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2016, Volume: 52, Number: 10, Pages: 1444-1451 Pages count : 8 DOI: 10.1134/S1070428016100134

Authors

Savel'ev V.A. ¹ , Tikhonov A.Ya. ¹ , Rybalova T.V. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, Vorozhtsov Novosibirsk Inst Organ Chem, Pr Akad Lavrenteva 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Ul Pirogova 2, Novosibirsk 630090, Russia

omega-(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 alpha-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.

Savel'ev V.A. , Tikhonov A.Y. , Rybalova T.V.
Formation of omega-(4-oxo-1,4-dihydropyridin-2-yl)alkanamides in the Beckmann rearrangement of spiro-fused cycloalkanone oximes
Russian Journal of Organic Chemistry. 2016. V.52. N10. P.1444-1451. DOI: 10.1134/S1070428016100134 WOS Scopus РИНЦ

Савельев В.А. , Тихонов А.Я. , Рыбалова Т.В.
Образование амидов ω-(4-оксо-1,4-дигидропиридин-2-ил)-алканкарбоновых кислот при перегруппировке бекмана спиросочлененных циклоалканоноксимов
Журнал органической химии (RUSS J ORG CHEM+). 2016. Т.52. №10. С.1454-1460. РИНЦ

Published print:	Oct 1, 2016
Published online:	Nov 25, 2016

Web of science	WOS:000388982200013
Scopus	2-s2.0-84996540060
Elibrary	27574092
OpenAlex	W2551959113