Catalytic synthesis of 1,2-azole and pyridine derivatives of 1,8-dioxooctahydroxanthenes using FIBAN K-1 fibrous sulfonic cation exchanger

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

Arylmethylenebis(3-hydroxy-2-cyclohexen-1-ones) were obtained by condensation of 1,2-azole- and pyridine-substituted aromatic aldehydes of the vanillin series with 1,3-cyclohexanedione in methanol in the presence of trimethylamine. Catalytic cyclization using fibrous sulfocationite FIBAN K-1 gave corresponding 1,8-dioxooctahydroxanthenes.

作者简介

E. Akishina

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Email: che.semenovaea@mail.ru

E. Dikusar

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

A. Polikarpov

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

K. Alekseeva

Peoples’ Friendship University of Russia (RUDN University)

D. Menshikova

Peoples’ Friendship University of Russia (RUDN University)

P. Kurman

Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus

V. Potkin

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

参考

  1. Maia M., Resende D.I.S.P., Durães F., Pinto M.M.M., Sousa E. // Eur. J. Med. Chem. 2021. Vol. 210. N 113085. doi: 10.1016/j.ejmech.2020.113085
  2. Ghahsare A.G., Nazifi Z.S., Nazifi S.M.R. // Curr. Org. Synth. 2019. Vol. 16. N 8. P. 1071. doi: 10.2174/1570179416666191017094908
  3. Al-Kadhemy M.F.H., Abbas K.N., Abdalmuhdi W.B. // IOP Conf. Series: Materials Science and Engineering. 2020. Vol. 928. P. 072126. doi: 10.1088/1757-899X/928/7/072126
  4. Ebaston T.M., Nakonechny F., Talalai E., Gellerman G., Patsenker L. // Dyes Pigm. 2021. Vol. 184. N 108854. doi: 10.1016/j.dyepig.2020.108854
  5. Wang L.G., Munhenzva I., Sibrian-Vazquez M., Escobedo J.O., Kitts C.H., Fronczek F.R., Strongin R.M. // J. Org. Chem. 2019. Vol. 84. N 5. P. 2585. doi: 10.1021/acs.joc.8b03030
  6. Burange A.S., Gadam K.G., Tugaonkar P.S., Thakur S.D., Soni R.K., Khan R.R., Tai M.S., Gopinath C.S. // Environ. Chem. Lett. 2021. Vol. 19. N 4. P. 3283. doi: 10.1007/s10311-021-01223-w
  7. Shirini F., Abedini M., Akbari-Dadamahaleh S., Rahmaninia A. // J. Iran. Chem. Soc. 2013. Vol. 11. N 3. P. 791. doi: 10.1007/s13738-013-0353-y
  8. Sunkara J. R., Botsa S. M. // Curr. Catal. 2020. Vol. 9. N 1. P. 72. doi: 10.2174/2211544708666191112120505
  9. Soleimani E., Khodaei M.M., Kal-Koshvandi A.T. // Chin. Chem. Lett. 2011. Vol. 22. N 8. P. 927. doi: 10.1016/j.cclet.2011.01.012
  10. Nasseri M.A., Kazemnejadi M., Mahmoudi B., Assadzadeh F., Alavi S.A., Allahresani A. // J. Nanopart. Res. 2019. Vol. 21. N 10. P. 214. doi: 10.1007/s11051-019-4643-x
  11. Babu G.N., Belay W., Endale T. // Cogent Chem. 2019. Vol. 5. N 1. P. 1708160. doi: 10.1080/23312009.2019.1708160
  12. Kuarm B.S., Madhav J.V., Laxmi S.V., Rajitha B., Reddy Y.T., Reddy P.N., Crooks P.A. // Synth. Commun. 2011. Vol. 41. N 12. P. 1719. doi: 10.1080/00397911.2010.492076
  13. Sheikh S., Nasseri M. A., Chahkandi M., Allahresani A., Reiser O. // J. Hazard. Mater. 2020. Vol. 400. P. 122985. doi: 10.1016/j.jhazmat.2020.122985
  14. Nandi M., Mondal J., Sarkar K., Yamauchi Y., Bhaumik A. // Chem. Commun. 2011. Vol. 47. N 23. P. 6677. doi: 10.1039/C1CC11007A
  15. Saravanamurugan S., Sujandi, Prasetyanto E.A., Park S.-E. // Micropor. Mesopor. Mater. 2008. Vol. 112. N 1-3. P. 97. doi: 10.1016/j.micromeso.2007.09.013
  16. Sadati Sorkhi S.E., Hashemi M.M., Ezabadi A. // Res. Chem. Intermed. 2020. Vol. 46. N 4. P. 2229. doi: 10.1007/s11164-020-04089-9
  17. Ghafuri H., Yaghoubi S., Zand H.R.E. // Appl. Organomet. Chem. 2019. Vol. 33. N 10. P. e5149. doi: 10.1002/aoc.5149
  18. Khurana J.M., Magoo D. // Tetrahedron Lett. 2009. Vol. 50. N 33. P. 4777. doi: 10.1016/j.tetlet.2009.06.029
  19. Yoshioka E., Kohtani S., Miyabe H. // Angew. Chem. Int. Ed. Vol. 50. N 29. P. 6638. doi: 10.1002/anie.201102088
  20. Halimehjani A. Z., Barati V. // ChemistrySelect. 2018. Vol. 3. N 11. P. 3024. doi: 10.1002/slct.201800060
  21. Prasad D., Preetam A., Nath M. // C. R. Chim. 2013. Vol. 16. N 12. P. 1153. doi: 10.1016/j.crci.2013.05.011
  22. Zhang P., Yu Y., Zhang Z. // Synth. Commun. 2008. Vol. 38. N. 24. P. 4474. doi: 10.1080/00397910802369604
  23. Nazari S., Keshavarz M., Karami B., Iravani N., Vafaee-Nezhad M. // Chin. Chem. Lett. 2014. Vol. 25. N 2. P. 317. doi: 10.1016/j.cclet.2013.12.011
  24. Sadjadi S., Koohesterani F., Heravi M. M. // Sci. Rep. 2020. Vol. 10. N 1. P. 19666. doi: 10.1038/s41598-020-76795-8
  25. Sadjadi S., Ghoreyshi Kahangi F., Dorraj M., Heravi M.M. // Molecules. 2020. Vol. 25. N 2. P. 241. doi: 10.3390/molecules25020241
  26. Al-Majid A.M., Islam M.S., Barakat A., Al-Qahtani N.J., Yousuf S., Iqbal Choudhary M. // Arab. J. Chem. 2017. Vol. 10. N 2. P. 185. doi: 10.1016/j.arabjc.2014.04.008
  27. Zabihzadeh M., Shirini F., Tajik H., Daneshvar N. // Polycycl. Aromat. Compd. 2021. Vol. 41. N 9. P. 1972. doi: 10.1080/10406638.2019.1708419
  28. Azizi N., Dezfooli S., Hashemi M.M. // C. R. Chim. 2013. Vol. 16. N 11. P. 997
  29. Maleki B., Raei M., Alinezhad H., Tayebee R., Sedrpoushan A. // Org. Prep. Proced. Int. 2018. Vol. 50. N 3. P. 288. doi: 10.1080/00304948.2018.1462055
  30. Поликарпов А.П., Шункевич А.А., Грачек В.И., Медяк Г.В. // Рос. хим. ж. 2015. Т. 59. № 3. С. 102.
  31. Дикусар Е.А., Поткин В.И., Козло Н.Г., Павлюченкова А.С., Мурашова М.Ю., Петкевич С.К., Клецков А.В., Поликарпов А.П., Огородникова М.М., Золотарь Р.М., Чепик О.П. // ЖОрХ. 2013. Т. 49. № 2. C. 243
  32. Dikusar E.A., Potkin V.I., Kozlov N.G., Pavlyuchenkova A.S., Murashova M.Yu., Petkevich S.K., Kletskov A.V., Polikarpov A.P., Ogorodnikova M.M., Zolotar' R.M., Chepik O.P. // Russ. J. Org. Chem. 2013. Vol. 49. N 2. P. 233. doi: 10.1134/s1070428013020103
  33. Sowmiah S., Esperança J.M.S.S., Rebelo L.P.N., Afonso C.A.M. // Org. Chem. Front. 2018. Vol. 5. N 3. P. 453. doi: 10.1039/C7QO00836H
  34. Акишина Е.А., Казак Д.В., Дикусар Е.А. // Вес. Нац. акад. навук Беларусi. Сер. хiм. навук. 2020. Т. 56. № 3. С. 301. doi: 10.29235/1561-8331-2020-56-3-301-310
  35. Поткин В.И., Петкевич С.К., Клецков А.В., Дикусар Е.А., Зубенко Ю.С., Жуковская Н.А., Казбанов В.В., Пашкевич С.Г. // ЖОрХ. 2013. Т. 49. № 10. С. 15430.
  36. Potkin V. I., Petkevich S.K., Kletskov A.V., Dikusar E.A., Zubenko Y.S., Zhukovskaya N.A., Kazbanov V.V., Pashkevich S.G. // Russ. J. Org. Chem. 2013. Vol. 49. N 10. P. 1523. doi: 10.1134/s1070428013100205

版权所有 © Russian Academy of Sciences, 2023

##common.cookie##