Quaternization of Methyl Picolinate with Some Phenacyl Bromides. Synthesis of DL-Baikiain Alkaloid
- Autores: Lomov D.1, Abramyants M.1, Zaporozhets O.1, Pekhtereva T.1
-
Afiliações:
- L. M. Litvinenko Institute of Physical Organic and Coal Chemistry
- Edição: Volume 94, Nº 1 (2024)
- Páginas: 105-112
- Seção: Articles
- URL: https://journals.rcsi.science/0044-460X/article/view/258263
- DOI: https://doi.org/10.31857/S0044460X24010095
- EDN: https://elibrary.ru/HKQMKV
- ID: 258263
Citar
Resumo
By fusing methyl picolinate with phenacyl bromides, the corresponding phenacyl salts were obtained, cyclization of which in acetic anhydride led to previously undescribed 3-aryl-1H-pyrido[2,1-c][1,4]oxazinium bromides. Reduction of the quaternary salts of methyl picolinate followed by acid hydrolysis leads to the alkaloid DL-baikiain.
Palavras-chave
Texto integral
Sobre autores
D. Lomov
L. M. Litvinenko Institute of Physical Organic and Coal Chemistry
Autor responsável pela correspondência
Email: lomov_dmitrii@mail.ru
Rússia, Donetsk
M. Abramyants
L. M. Litvinenko Institute of Physical Organic and Coal Chemistry
Email: lomov_dmitrii@mail.ru
Rússia, Donetsk
O. Zaporozhets
L. M. Litvinenko Institute of Physical Organic and Coal Chemistry
Email: lomov_dmitrii@mail.ru
Rússia, Donetsk
T. Pekhtereva
L. M. Litvinenko Institute of Physical Organic and Coal Chemistry
Email: lomov_dmitrii@mail.ru
Rússia, Donetsk
Bibliografia
- King F.E., King T.J., Warwick A.J. // J. Chem. Soc. 1950. P. 3590. doi: 10.1039/JR9500003590
- Kornprobst J.-M. Encyclopedia of Marine Natural Products. New Jersey: Wiley-VCH Verlag GmbH & Co., 2014. Vol. 1. P. 328.
- Pelletier S.W. In: Alkaloids: Chemical and Biological Perspectives. New York: Springer-Verlag, 1992. Vol. 8. P. 154. doi: 10.1007/978-1-4612-2908-7_2
- Davis J.L., Gerbrandt L.K., Cherkin A. // Physiol. Behav. 1978. Vol. 21. P. 653. doi: 10.1016/0031-9384(78)90144-0
- Alegret C., Riera A. // J. Org. Chem. 2008. Vol. 73. P. 8661. doi: 10.1021/jo801645p
- Leete E., Mueller M.E. // J. Am. Chem. Soc. 1982. Vol. 104. P. 6440. doi: 10.1021/ja00387a048
- Verma M., Beaulieu-Abdelahad D., Ait-Ghezala G., Li, R., Crawford F., Mullan M., Paris D. // PLoS One. 2015. Vol. 10. N 5. P. e0128224. doi: 10.1371/journal.pone.012822
- Schmeltz L.R., Blevins T.C., Aronoff S.L., Ozer K., Leffert J.D., Goldberg M.A., Horowitz B.S., Bertenshaw R.H., Troya P., Cohen A.E., Lanier R.K., Wright IV C. // J. Clin. Endocrinol. Metab. 2014. Vol. 99. N 1. P. e137. doi: 10.1210/jc.2013-2951
- Laniera R.K., Cohena A.E., Weinkle S.H. // Case Rep. Dermatol. 2013. Vol. 5. P. 347. doi: 10.1159/000357019
- Lanier R.K., Gibson K.D., Cohen A.E., Varga M. // Clin. Med. Insights: Arthritis and Musculoskeletal Disorders. 2013. Vol. 6. P. 73. doi: 10.4137/CMAMD.S13001
- Dobson N.A., Raphael R.A. // J. Chem. Soc. 1958. P. 3642. doi: 10.1039/JR9580003642
- Burgstahler A.W., Aiman C.E. // J. Org. Chem. 1960. Vol. 25. P. 489. doi: 10.1021/jo01074a001
- Herdeis C., Engel W. // Arch. Pharm. 1993. Vol. 326. P. 297. doi: 10.1002/ardp.19933260509
- Ginesta X., Pericas M.A., Riera A. // Tetrahedron Lett. 2002. Vol. 43. P. 779. doi: 10.1016/S0040-4039(01)02271-7
- Kim C.M.F. Tjen, Kinderman S.S., Schoemaker H.E., Hiemstra H., Floris P.J.T. Rutjes // Chem. Comm. 2000. P. 699. doi: 10.1039/b001253j
- Floris P.J.T. Rutjes, Schoemaker H.E. // Tetrahedron Lett. 1997. Vol. 38. N 4. P. 677. doi: 10.1016/S0040-4039(96)02390-8
- Chang M.-Y., Kung Y.-H., Wu T.-C. // Heterocycles. 2006. Vol. 68. N 11. P. 2365. doi: 10.3987/COM-06-10874
- Mazon A., Najera C. // Tetrahedron Asym. 1997. Vol. 8. N 11. P. 1855. doi: 10.1016/S0957-4166(97)00180-8
- Servatius P., Kazmaier U. // Synlett. 2015 Vol. 26. N 14. P. 2001. doi: 10.1055/s-0034-1378720
- Ломов Д.А., Абрамянц М.Г., Запорожец О.О., Пехтерева Т.М. // ЖОрХ. 2022. Т. 58. Вып. 6. С. 632; Lomov D.A., Abramyants M.G., Zaporozhets O.O., Pekhtereva T.M. // Russ. J. Org. Chem. Vol. 58. N 4. P. 791. doi: 10.1134/S1070428022060057
- Абрамянц М.Г., Ломов Д.А., Лящук С.Н., Запорожец О.О. // ЖОрХ. 2018. Т. 54. Вып. 4. С. 591; Abramyants M.G., Lomov D.A., Lyashchuk S.N., Zaporozhets O.O. // Russ. J. Org. Chem. Vol. 54. N 4. P. 593. doi: 10.1134/S1070428018040139