Synthesis of 5-Aryl-4-thioxo-2,3,4,5,6,8-hexahydro-7H-pyrido[3,2-e][1,3]thiazine-7-ones

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Upon interaction of N-methylmorpholinium 4-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates with hydrogen sulfide and formaldehyde in ethanol 5-aryl-4-thioxo-2,3,4,5,6,8-hexahydro-7H-pyrido[3,2-e][1,3]thiazine-7-ones were obtained. The molecular and crystal structures of N-methylmorpholinium 5-cyano-4-(3,4,5-trimethoxyphenyl)-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolate were studied using X-ray diffraction analysis.

Full Text

Restricted Access

About the authors

К. А. Frolov

V. Dahl Lugansk State University

Author for correspondence.
Email: ksg-group-lugansk@mail.ru
ORCID iD: 0000-0002-8045-7582

Chemex Lab

Russian Federation, kv. Molodyozhny 20-A/7, Lugansk, 291034

B. S. Krivokolysko

V. Dahl Lugansk State University

Email: ksg-group-lugansk@mail.ru
ORCID iD: 0000-0002-3181-7609

Chemex Lab

Russian Federation, kv. Molodyozhny 20-A/7, Lugansk, 291034

V. V. Dotsenko

Kuban State University

Email: ksg-group-lugansk@mail.ru
ORCID iD: 0000-0001-7163-0497
Russian Federation, ul. Stavropolskaya, 149, Krasnodar, 350040

N. A. Aksenov A. Aksenov

North Caucasus Federal University

Email: ksg-group-lugansk@mail.ru
ORCID iD: 0000-0002-7125-9066
Russian Federation, ul. Pushkina, 1-A, Stavropol, 355009

S. G. Krivokolysko

V. Dahl Lugansk State University

Email: ksg-group-lugansk@mail.ru
ORCID iD: 0000-0001-9879-9217

Chemex Lab

Russian Federation, kv. Molodyozhny 20-A/7, Lugansk, 291034

References

  1. Hua С., Le H., Mo Z., Tianyu Y., Sinan W., Zhanbin Q., Pingzhu Z., Xiaoliu L. Bioorg. Med. Chem. Lett. 2014, 24, 3426–3429. doi: 10.1016/j.bmcl.2014.05.079
  2. Silverberg L.J., Mal T.K., Pacheco C.N., Povelones M.L., Malfara M.F., Lagalante A.F., Olsen M.A., Yennawar H.P., Sobhi H.F., Baney K.R., Bozeman R.L., Eroh C.S., Fleming M.J., Garcia T.L., Gregory C.L., Hahn J.E., Hatter A.M., Johns L.L., Klinger T.L., Li J.J. Molecules. 2021, 26, 6099. doi: 10.3390/molecules26206099
  3. Hiroshi I., Jun-Ichi Sh., Tomoyuki Y., Kazushige O., Hiroshi Y., Kota K., Shuichi S. Bioorg. Med. Chem. 2015, 23, 1788–1799. doi: 10.1016/j.bmc.2015.02.033
  4. Hamed E.O., Assy M.G., Shalaby A.M., Sayed R.E. ЖОрХ. 2020, 11, 2005–2013. [Hamed E.O., Assy M.G., Shalaby A.M., Sayed R.E. Russ. J. Org. Chem. 2020, 56, 2005–2013.] doi: 10.1134/S1070428020110159
  5. Kapil A., Pooja T., Jyoti S. RSC Adv. 2014, 4, 3060–3064. doi: 10.1039/C3RA43908A
  6. Hamama W.S., Waly M.A., El-Hawary I.I., Zoorob H.H. J. Heterocycl. Chem. 2016, 53, 953–957. doi: 10.1002/jhet.1631
  7. Ogurtsov V.A., Karpychev Yu.V., Nelyubina Yu.V., Primakov P.V., Koutentis P.A., Rakitin O.A. Eur. J. Org. Chem. 2019, 26, 4149–4158. doi: 10.1002/ejoc.201900142
  8. Shengzheng W., Kun F., Guoqiang D., Shuqiang Ch., Na L., Zhenyuan M., Jianzhong Y., Jian L., Wannian Zh., Chunquan Sh. J. Med. Chem. 2015, 58, 6678–6696. doi: 10.1021/acs.jmedchem.5b00910
  9. Silverberg L. J. Пат. WO2020/237063 (2020). США.
  10. Краузе А., Дубурс Г. ХГС. 2001, 3, 404–405. [Krauze A., Duburs G. Chem. Heterocycl. Comp. 2001, 37, 378–379.] doi: 10.1023/A:1017535922740
  11. Dotsenko V.V., Frolov K.A., Pekhtereva T.M., Papaianina O.S., Suykov S.Yu., Krivokolysko S.G. ACS Comb. Sci. 2014, 16, 543–550. doi: 10.1021/co5000807
  12. Ахметова В.Р., Рахимова Е.Б. ЖОрХ. 2014, 50, 1727–1749. [Akhmetova V.R., Rakhimova E.B. Russ. J. Org. Chem. 2014, 50, 1711–1731.] doi: 10.1134/S107042801412001X
  13. Нестеров В.Н., Кривоколыско С.Г., Дяченко В.Д., Доценко В.В., Литвинов В.П. Изв. АН. Сер. хим. 1997, 5, 1029–1034. [Nesterov V.N., Krivokolysko S.G., Dyachenko V.D., Dotsenko V.V., Litvinov V.P. Russ. Chem. Bull. 1997, 46, 990–996.] doi: 10.1007/BF02496132
  14. Dotsenko V.V., Frolov K.A., Pekhtereva T.M., Papaianina O.S., Suykov S.Yu., Krivokolysko S.G. ACS Comb. Sci. 2014, 16, 543–550. doi: 10.1021/co5000807
  15. Дяченко В.Д., Кривоколыско С.Г., Литвинов В.П. Изв. АН. Сер. хим. 1997, 10, 1852–1856. [Dyachenko V.D., Krivokolysko S.G., Litvinov V.P. Russ. Chem. Bull. 1997, 46, 1758–1762.] doi: 10.1007/BF02495131
  16. Dotsenko V.V. Bushmarinov I.S., Goloveshkin A.S., Chigorina E.A., Frolov K.A., Krivokolysko S.G. Phosph., Sulfur Silicon Relat. Elem. 2017, 192, 47–52. doi: 10.1080/10426507.2016.1224877
  17. Доценко В.В., Кривоколыско С.Г., Чернега А.Н., Литвинов В.П. Докл. АН. 2003, 389, 763–767. [Dotsenko V.V., Krivokolysko S.G., Chernega A.N., Litvinov V.P. Doklady Chem. 2003, 389, 92–96.] doi: 10.1023/A:1023492608275
  18. Доценко В.В., Лебедева И.А., Кривоколыско С.Г., Повстяной М.В., Повстяной В.М., Костирко Е.О. ХГС. 2012, 48, 492–499. [Dotsenko V.V., Lebedeva I.A., Krivokolysko S.G., Povstyanoi M.V., Povstyanoi V.M., Kostyrko E.O. Chem. Heterocycl. Comp. 2012, 48, 462–469.] doi: 10.1007/s10593-012-1016-0
  19. Dolomanov O.V., Bourhis L.J., Gildea R.J, Howard J.A.K., Puschmann H. J. Appl. Cryst. 2009, 42, 339–341. doi: 10.1107/S0021889808042726
  20. Sheldrick G.M. Acta Cryst. 2008, A64, 112–122. doi: 10.1107/S0108767307043930
  21. Sheldrick G. M. Acta Cryst. 2015, C71, 3–8. doi: 10.1107/S2053229614024218

Supplementary files

Supplementary Files
Action
1. JATS XML
2. Схема 1a - f, 2a-f: Ar = 2-ClC6H4 (a), 4-Meoc6h4 (b), 2-MeC6H4 (c), 2-EtOC6H4 (d), 2,5-(MeO) 2C6H3 (e), 3,4,5-(MeO)3C6H2 (f)

Download (144KB)
3. Table

Download (141KB)
4. Formulas

Download (51KB)
5. Fig. Atomic and molecular structure of compound 1f. Thermal ellipsoids of non-hydrogen atoms are shown at a 50% probability of finding an atom.

Download (251KB)

Copyright (c) 2024 Russian Academy of Sciences