SYNTHESIS OF 5,5-DISUBSTITUTED  N -METHYL-1,3-OXAZINANES CONTAINING MONOTERPENE FRAGMENTS

I. V. Nechepurenko; Нечепуренко И. В.; K. P. Volcho; Волчо К. П.; N. F. Salakhutdinov; Салахутдинов Н. Ф.

doi:10.31857/S2686953522600283

SYNTHESIS OF 5,5-DISUBSTITUTED N-METHYL-1,3-OXAZINANES CONTAINING MONOTERPENE FRAGMENTS

Autores: Nechepurenko I.¹, Volcho K.¹, Salakhutdinov N.¹
Afiliações:
1. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences (NIOCH SB RAS)
Edição: Volume 512, Nº 1 (2023)
Páginas: 75-82
Seção: ХИМИЯ
URL: https://journals.rcsi.science/2686-9535/article/view/247184
DOI: https://doi.org/10.31857/S2686953522600283
EDN: https://elibrary.ru/UYVBYE
ID: 247184

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Resumo

A new method for the synthesis of 5,5-disubstituted N-methyl-1,3-oxazinanes as a mixture of diastereomers at position 5 containing monoterpene and branched alkyl substituents at position 5 has been developed. The 1,3-oxazinanes were obtained for the first time by the interaction of 2,2-substituted 3-aminopropane-1-ols with formaldehyde and sodium borohydrides in a single stage.

Palavras-chave

oxazine, tetrahydro-1,3-oxazine, oxazinane, aminopropanol, propanolamine, pinene, Knoevenagel condensation, alkylation of cyanoacetic ether, cyanoethylacetate

Sobre autores

I. Nechepurenko

Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences (NIOCH SB RAS)

Autor responsável pela correspondência
Email: niv@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

K. Volcho

Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences (NIOCH SB RAS)

Email: niv@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

N. Salakhutdinov

Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences (NIOCH SB RAS)

Email: niv@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

Bibliografia

Khuong-Huu F., Herlem-Gaulier D., Khuong-Huu M.Q., Stanislas E., Goutarel R. // Tetrahedron. 1966. V. 22. № 10. P. 3321–3327. https://doi.org/10.1016/S0040-4020(01)92518-9
Choudhary M.I., Atta-ur-Rahman, Shamma M. // Phytochemistry. 1988. V. 27. № 5. P. 1561–1562. https://doi.org/10.1016/0031-9422(88)80246-2
Lázár L., Fülöp F. 1,3-Oxazines and their benzo derivatives. In: Comprehensive heterocyclic chemistry III. Katritzky A., Ramsden Ch., Scriven E., Taylor R. (Eds.). V. 8. Elsevier Ltd., 2008. P. 395–400. https://doi.org/10.1016/B978-008044992-0.00705-7
Pardin C., Pelletier J.N., Lubell W.D., Keillor J.W. // J. Org. Chem. 2008. V. 73. № 15. P. 5766–5775. https://doi.org/10.1021/jo8004843
Knabe J., Buchheit W. // Arch. Pharm. 1985. V. 318. № 8. P. 727–735. https://doi.org/10.1002/ardp.19853180811
Forró E., Fülöp F. // Tetrahedron: Asymmetry. 1999. V. 10. № 10. P. 1985–1993. https://doi.org/10.1016/S0957-4166(99)00189-5
Корепин А.Г., Галкин П.В., Глушакова Н.М., Лоды-гина В.П., Еременко И.Л., Нефедов С.Е., Еремен-ко Л.Т. // Изв. АН. Сер. хим. 2001. № 9. С. 1553–1561. https://doi.org/10.1023/A:1013094720611
Frasinyuk M.S., Bondarenko S.P., Khilya V.P., Liu Ch., Watt D.S., Sviripa V.M. // Org. Biomol. Chem. 2015. V. 13. № 4. P. 1053–1067. https://doi.org/10.1039/C4OB02137A
Яровая О.И., Салахутдинов Н.Ф. // Усп. хим. 2021. Т. 90. № 4. С. 488–510. https://doi.org/10.1070/RCR4969
Патрушева О.С., Волчо К.П., Салахутдинов Н.Ф. // Усп. хим. 2018. Т. 87. № 8. С. 771–796. https://doi.org/10.1070/RCR4810
Salaverri N., Carli B., Gratal P.B., Marzo L., Alemán J. // Adv. Synth. Catal. 2022. V. 364. P. 1689–1694. Suppl. Inf. https://doi.org/10.1002/adsc.202200220
Банина О.А., Судариков Д.В., Крымская Ю.В., Фролова Л.Л., Кучин А.В. // ХПС. 2015. № 2. С. 231–234. https://doi.org/10.1007/s10600-015-1257-0
Demidova Yu.S., Suslov E.V., Simakova I.L., Mozhaj-cev E.S., Korchagina D.V., Volcho K.P., Salakhutdinov N.F., Simakov A., Murzine D.Yu. // J. Mol. Catal. A: Chem. 2017. V. 426. P. 60–67. https://doi.org/10.1016/j.molcata.2016.10.034
Pascual C., Meier J., Simon W. // Helv. Chim. Acta. 1966. V. 49. № 1. P. 164–168. https://doi.org/10.1002/hlca.660490122
Smith S.N., Craig R., Connon S.J. // Chem. Eur. J. 2020. V. 26. № 59. P. 13378–13382. https://doi.org/10.1002/chem.202003280
Беккер Х., Беккерт Р., Бергер В., Гевальд К., Генц Ф., Глух Р., Домшке Г., Зайлер Э., Майер Р., Мец П., Мюллер К., Пафель Д., Фаигхенелъ Э., Фауст Ю., Фишер М., Хабихер В., Шветлик К., Шмидт Г., Шольберг К., Цеппенфельд Г. Органикум: в 2-х т. Пер. с нем., 4-е изд. Т. 2. М.: Мир, 2008. с. 125. (Becker H., Berger W., Domschke G., Fanghanel E., Faust J., Fischer M., Gentz F., Gewald K., Gluch R., Mayer R., Habicher W.D., Metz P., Muller K., Pavel D., Schmidt H., Schollberg K., Schwetlick K., Seiler E., Zeppenfeld G. Organikum. Organisch-chemisches Grundpraktikum. 22nd edn. Wiley-VCH GmbH, Weinheim, 2004. 914 p.)
Ramachary D.B., Kishor M., Reddy Y.V. // Eur. J. Org. Chem. 2008. № 6. P. 975–993. Suppl. Inf. https://doi.org/10.1002/ejoc.200701014