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

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Abstract

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 C2, 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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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    V. A. Savel’ev, A. Ya. Tikhonov & T. V. Rybalova

  2. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090, Russia

    T. V. Rybalova

Authors
  1. V. A. Savel’ev
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  2. A. Ya. Tikhonov
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  3. T. V. Rybalova
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Correspondence to V. A. Savel’ev.

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Original Russian Text © V.A. Savel’ev, A.Ya. Tikhonov, T.V. Rybalova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 10, pp. 1454–1460.

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Savel’ev, V.A., Tikhonov, A.Y. & Rybalova, T.V. Formation of ω-(4-oxo-1,4-dihydropyridin-2-yl)alkanamides in the Beckmann rearrangement of spiro-fused cycloalkanone oximes. Russ J Org Chem 52, 1444–1451 (2016). https://doi.org/10.1134/S1070428016100134

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  • DOI: https://doi.org/10.1134/S1070428016100134

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