Multicomponent synthesis of functionalized 2-amino-4H-pyrans initiated by the Knoevenagel reaction

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Abstract

The multicomponent condensation of aldehydes, malononitrile derivatives, 1,3-dicarbonyl compounds of the carbo- and heterocyclic series, and alkyl halides has been studied. The transformation is initiated by the Knoevenagel reaction and leads to the formation of functionally substituted condensed 2-amino- 4 H-pyrans. The structure of a number of products was studied by X-ray diffraction.

About the authors

I. V Dyachenko

Lugansk State Pedagogical University

Email: nenajdenko@gmail.com

V. D Dyachenko

Lugansk State Pedagogical University

Email: nenajdenko@gmail.com

P. V Dorovatovskii

National Research Center “Kurchatov Institute”

Email: nenajdenko@gmail.com

V. N Khrustalev

Peoples’ Friendship University of Russia (RUDN University);Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: nenajdenko@gmail.com

V. G Nenajdenko

Lomonosov Moscow State University

Email: nenajdenko@gmail.com

References

  1. Mahmoud N.F.H., El-Bordany E.A., Elsaed G.A. J. Chem. 2017, 5373049. doi: 10.1155/2017/5373049
  2. El-Shwiniy W.H., Shehab W.S., Zordok W.A. J. Mol. Struct. 2020, 1199, 126993
  3. Drewe J.A., Xiong C.S., Wang Y. Пат. 6906203 (2005). США. РЖХим. 2006. 06.14-19О.57П.
  4. Шевердов В.П., Андреев А.Ю., Насакин О.Е., Гейн В.Л. Хим.-фарм. ж. 2014, 48, 25-28.
  5. Nakhi A., Rahman M.S., Archana S., Kishore R., Seerapu G.P.K., Kumar K.L., Halofar D., Pal M. Bioorg. Med. Chem. Lett. 2013, 23, 4195-4205. doi: 10.1016/j.bmcl.2013.05.014
  6. Kandile N.G., Zaky H.T. J. Enzyme Inhib. Med. Chem. 2015, 30, 44-51. doi: 10.3109/14756366.2013.877896
  7. Dardari Z., Lemrani M., Sebban A., Bahloul A., Hassar M., Kitane S., Berrada M., Boudouma B. Arch. Pharm. 2006, 339, 291-298. doi: 10.1002/ardp.200500266
  8. Ali T.E., Bakhotmah D.A., Assiri M.A. Synth. Commun. 2020, 50, 3314-3325. doi: 10.1080/00397911.2020.1800744
  9. Saundane A.R., Walmic P., Yarlakatti M., Kutkar V., Verma V.A. J. Heterocycl. Chem. 2014, 51, 303-314. doi: 10.1002/jhet.1582
  10. Kumar B.S., Lakshmi P.V.A., Veena B.S., Sujatha E. Russ. J. Gen. Chem. 2017, 87, 829-836. doi: 10.1134/S1070363217040260
  11. Dorostkar-Ahmadi N., Davoodnia A., Tavakoli-Hoseini N., Behmadi H., Nakhaei-Moghaddam M. Z. Naturforsh. B Chem. Sci. 2019, 74, 175-181. doi: 10.1515/znb-2018-0166
  12. Kaur M., Kaur A., Mankotia S., Singh H., Singh A., Virsingh J., Kupta M.K., Sharma S., Depali K., Bedi P.M.S. Eur. J. Med. Chem. 2017, 131, 14-28. doi: 10.1016/j.ejmech.2017.03.002
  13. Shehab W.S., El-Shwiniy W.H. J. Iranian Chem. Soc. 2018, 15, 431-443. doi: 10.1007/s13738-017-1244-4
  14. Erichsen M.N., Huynh T.H., Abrahamsen B., Bastlund J.F., Bundgaard C., Monrad O., Bekker-Jensen A., Nielsen C.W., Frydenvang K., Jensen A.A., Bunch L. J. Med. Chem. 2010, 53, 7180-7191. doi: 10.1021/jm1009154
  15. Дяченко И.В., Дяченко В.Д., Дороватовский П.В., Хрусталев В.Н., Ненайденко В.Г. ЖОрХ. 2019, 55, 266-278.
  16. Dyachenko I.V., Dyachenko V.D., Dorovatovskii P.V., Khrustalev V.N., Nenajdenko V.G. Russ. J. Org. Chem. 2019, 55, 215-226. doi: 10.1134/S1070428019020131
  17. Дяченко И.В., Дяченко В.Д., Дороватовский П.В., Хрусталев В.Н., Ненайденко В.Г. ЖОрХ. 2020, 56, 993-1003.
  18. Dyachenko I.V., Dyachenko V.D., Dorovatovskii P.V., Khrustalev V.N., Nenajdenko V.G. Russ. J. Org. Chem. 2020, 56, 1123-1131. doi: 10.1134/S1070428020070015
  19. Дяченко В.Д. ЖОХ. 2005, 75, 476-482.
  20. Dyachenko V.D. Russ. J. Gen. Chem. 2005, 75, 440-446. doi: 10.1007/s11176-005-0247-5
  21. Дяченко В.Д. ЖОХ. 2006, 76, 299-308.
  22. Dyachenko V.D. Russ. J. Gen. Chem. 2006, 76, 282-291. doi: 10.1134/S1070363206020216
  23. Клокол Г.В., Кривоколыско С.Г., Дяченко В.Д., Литвинов В.П. ХГС. 1999, 35, 1363-1366.
  24. Klokol G.V., Krivokolisko S.G., Dyachenko V.D., Litvinov V.P. Chem. Heterocycl. Compd. 1999, 35, 1183-1186. doi: 10.1007/BF02323376
  25. Frijia L.M.T., Pompeiro A.J.L., Kopylovich M.N. Coord. Chem. Rev. 2016, 308, 32-55. doi: 10.1016/j.ccr.2015.10.003
  26. Rouf A., Tanyeli C. Eur. J. Med. Chem. 2015, 97, 911-927. doi: 10.1016/j.ejmech.2014.10.058
  27. Bender W., Betz U., Kleymann G., Baumeister J., Eckenberg P., Fischer R., Handke-Ergueden G., Hendrix M., Heninger K., Jensen A., Keldenich J., Reefschloger J., Schmidt T., Schneider U., Weber O. Заявка 10210319 (2003). Германия. РЖХим. 2004. 04.22-19О.114П.
  28. Sanner M.A., Helal C.J., Cooper C.B. Пат. 6720427 (2004). США. РЖХим. 2005. 05.04-19О.172П.
  29. Dhanoa D.S., Ryan D.E., Deckman I., Sapienza A. Пат. 6586453 (2003). США. РЖХим. 2004. 04.05-19О.136П.
  30. Rawlins D.B., Kimball D.S., Kim K.S., Misra R.N., Webster K.R. Пат. 6720347 (2004). США. РЖХим. 2005. 05.06-19О.158П.
  31. Титце Л., Браше Г., Герике К. Домино-реакции в органическом синтезе. М.: Бином. Лаборатория знаний. 2010.
  32. Ненайденко В.Г. Усп. хим. 2020, 89, 1274-1336.
  33. Nenajdenko V.G. Russ. Chem. Rev. 2020, 89, 1274-1336. doi: 10.1070/RCR5010
  34. Metwally N.H., Abdelrazek F.M., Sobhy N.A. Afinidad. 2005, 62, 616-621.
  35. Shi D.-A., Yu C.-X., Zhuang Q.-Y., Wang X.-S. J. Chem. Res. 2006, 4, 225-227. doi: 10.3184/030823406776894184
  36. Nagamani M., Jalapathi P., Shankar B., Neelamma M., Krishna T.M. Russ. J. Gen. Chem. 2019, 89, 998-1002. doi: 10.1134/S1070363219050207
  37. Sun W., Jiang Y., Yan H., Song X. Austr. J. Chem. 2015, 68, 273-281. doi: 10.1071/CH14113
  38. Bruker, SAINT, Bruker AXS Inc., Madison, WI, 2013.
  39. SADABS 2016/2. Krause L., Herbst-Irmer R., Sheldrick G.M., Stalke D. J. Appl. Crystallogr. 2015, 48, 3-10. doi: 10.1107/S1600576714022985
  40. Battye T.G.G., Kontogiannis L., Johnson O., Powell H.R., Leslie A.G.W. Acta Crystallogr. Sect. D. 2011, 67, 271-281. doi: 10.1107/S0907444910048675
  41. Evans P.R. Acta Crystallogr., Sect. D. 2006, 62, 72-82. doi: 10.1107/S0907444905036693
  42. Sheldrick G.M. Acta Crystallogr., Sect. C. 2015, 71, 3-8. doi: 10.1107/S2053229614024218

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