3-(2-Methylphenyl)-2-selenoxo-2,3-dihydroquinazolin-4(1H)-one and Its Complex with Cd(II): Synthesis and Molecular and Crystal Structures
- Авторлар: Askerov R.K.1, Chipinskii E.V.2, Peregudov A.S.3, Osmanov V.K.2, Matsulevich Z.V.2, Borisova G.N.2, Khrustalev V.N.4,5, Smirnova O.N.6, Magerramov A.M.1, Borisov A.V.2
-
Мекемелер:
- Baku State University
- Nizhni Novgorod State Technical University
- Nesmeyanov Institute of Organic Element Compounds, Russian Academy of Sciences
- Peoples’ Friendship University of Russia
- Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
- National Research State University
- Шығарылым: Том 50, № 1 (2024)
- Беттер: 26-40
- Бөлім: Articles
- URL: https://genescells.com/0132-344X/article/view/667626
- DOI: https://doi.org/10.31857/S0132344X24010049
- EDN: https://elibrary.ru/OSNWSM
- ID: 667626
Дәйексөз келтіру
Аннотация
The reaction of methyl anthranilate with 2-methylphenyl-iso-selenocyanate in boiling absolute ethanol affords a new compound: 3-(2-methylphenyl)-2-selenoxo-2,3-dihydroquinazolin-4(1Н)-one (HL). Free ligand HL, which is selone, is preliminarily transformed into the corresponding sodium selenolate [C15H11N2OSeNa] (I), which is then used without isolation in the reaction with cadmium chloride. This reaction leads to the formation of complex [Cd2(μ-L)2(L)2(C2H5OH)2] (II). The structures of the compounds are determined by X-ray diffraction (XRD) (CIF files CCDC nos. 2142342 (НL) and 2246014 (II)) and NMR spectroscopy (1Н, 13С, 15N, and 77Se). In the crystal, the molecules of HL form one-dimensional chains due to H…O and H…Se contacts and alternate in the syndiotactic order. Compound II is the centrosymmetric binuclear complex [C64H56Cd2N8O6Se4]. The cadmium atoms in complex II are hexacoordinated by two chelate anionic ligands L–. According to the NMR data, in a DMSO-d6 solution free ligand HL has the selone structure, whereas in cadmium complex II this ligand exists in the selenolate form, which is consistent with the XRD data on the crystal structures of the compounds.
Авторлар туралы
R. Askerov
Baku State University
Хат алмасуға жауапты Автор.
Email: rizvankam@bk.ru
Әзірбайжан, Baku
E. Chipinskii
Nizhni Novgorod State Technical University
Email: rizvankam@bk.ru
Ресей, Nizhni Novgorod
A. Peregudov
Nesmeyanov Institute of Organic Element Compounds, Russian Academy of Sciences
Email: rizvankam@bk.ru
Ресей, Moscow
V. Osmanov
Nizhni Novgorod State Technical University
Email: rizvankam@bk.ru
Ресей, Nizhni Novgorod
Zh. Matsulevich
Nizhni Novgorod State Technical University
Email: rizvankam@bk.ru
Ресей, Nizhni Novgorod
G. Borisova
Nizhni Novgorod State Technical University
Email: rizvankam@bk.ru
Ресей, Nizhni Novgorod
V. Khrustalev
Peoples’ Friendship University of Russia; Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
Email: rizvankam@bk.ru
Ресей, Moscow; Moscow
O. Smirnova
National Research State University
Email: rizvankam@bk.ru
Ресей, Nizhni Novgorod
A. Magerramov
Baku State University
Email: rizvankam@bk.ru
Әзірбайжан, Baku
A. Borisov
Nizhni Novgorod State Technical University
Email: rizvankam@bk.ru
Ресей, Nizhni Novgorod
Әдебиет тізімі
- Shtefan E.D., Vvedenskii V. Y. // Russ. Chem. Rev. 1996. V. 65. P. 307. https://doi.org/10.1070/ RC1996v065n04ABEH000212
- Akkurt M., Ozturk S., Servi S. et al. // Acta Crystallogr. E. 2004. V. 60. P. 1507. https://doi.org/10.1107/S1600536804019099
- Buzykin B.I., Mironova E. V., Gubaidullin A. T. et al. // Russ. J. Gen. Chem. 2008. V. 78. № 4. P. 634. https://doi.org/10.1134/S107036320804021X
- Аскеров Р.К., Магерамов А. М., Османов В. К. и др. // Журн. структур. химии. 2018. Т. 59. № 7. С. 1717. https://doi.org/10.26902/JSC20180719.
- Askerov R.K., Magerramov A. M., Osmanov V. K. et al. // Russ. J. Coord. Chem. 2019. V. 45. № 2. P. 112. https://doi.org/10.1134/S1070328419020039
- Askerov R.K., Magerramov A. M., Osmanov V. K. et al. // Russ. J. Coord. Chem. 2019. V. 45. № 8. P. 668. https://doi.org/10.1134/S1070328419070017
- Rizvan K.A., Maharramov A. M., Khalilov A. N. et al. // Acta Crystallogr. E. 2020. P. 1007. https://doi.org/10.1107/S2056989020007033
- Osmanov V.K., Chipinski E. V., Askerov R. K. et al. // Russ. J. Coord. Chem. 2021. V. 47. № 1. P. 32. https://doi.org/10.1134/S1070328421010048
- Askerov R.K., Osmanov V. K., Kovaleva O. N. // Russ. J. Coord. Chem. 2021. V. 47. № 11. P. 741. https://doi.org/10.1134/S1070328421110014
- Osmanov V.K., Chipinsky E. V., Khrustalev V. N. // Molecules. 2022. V. 27. P. 5799. https://doi.org/10.3390/molecules27185799
- Song J.-F., Wang J., Li Si-Z. et. al. // J. Mol. Struct. 2017. V. 1129. P. 1.
- Hernandez-Arganis M., Moya-Cabrera M., Jancik V. et al. // Inorg. Chim. Acta. 2018. V. 475. P. 83. https://doi.org/10.1016/j.ica.2017.07.062
- Hernandez-Arganis M., Toscano R. A., Moya-Cabrera M. et al. // Z. Anorg. Allg. Chem. 2004. V. 630. P. 1627. https://doi.org/10.1002/zaac.200400183
- Muhammad I., Andreas M., Neumann B. et al. // Dalton Trans. 2014. V. 43. № 39. P. 14737. https://doi.org/10.1039/C4DT01931H
- Li Y., Wang C. Q., Bian H. D. // J. Coord. Chem. 2012. V. 65. № 20. P. 3665.
- Ilie A., Rat C. I., Scheutzow S. et al. // Inorg. Chem. 2011. V. 50. P. 2675. https://doi.org/10.1021/ic102595d
- Sanina N.A., Kozub G. I., Kondrat’eva T.A. et al. // J. Mol. Struct. 2013. V. 1041. P. 183. https://doi.org/10.1016/j.molstruc.2013.03.021
- Bharty M.K., Dani R. K., Kushawaha S. K. et al. // Polyhedron. 2015. V. 88. P. 208. https://doi.org/10.1016/j.poly.2015.05.045
- Taheriha M., Ghadermazi M., Amani V. // J. Mol. Struct. 2016. V. 1107. P. 57. https://doi.org/10.1016/j.molstruc.2015.11.012
- Askerov R.K., Youness El Bakri, Osmanov V. K. // J. Inorg. Biochem. 2022. V. 231. P. 111791. https://doi.org/10.1016/j.jinorgbio.2022.111791
- Askerov R.K., Ashfaq M., Chipinsky E. V. et al. // Results Chem. 2022. V. 4. 100600. https://doi.org/10.1016/j.rechem.2022.100600
- Yadav S., Deka R., Singh H. B. // Chem. Lett. 2019. V. 48. P. 65. https://doi.org/10.1246/cl.180748
- Yadav S., Singh H. B., Butcher R. J. // Eur. J. Inorg. Chem. 2017. V. 23. P. 2968. https://doi.org/10.1002/ejic.201700218
- Karri R., Chalana A., Kumar B. et al. // Chem. Eur. J. 2019. V. 25. № 55. P. 12810. https://doi.org/10.1002/chem.201902578
- Isab A.A., Wazeer M. I.M., Fettouhi M. et al. // Poly-hedron. 2006. V. 25. P. 2629. https://doi.org/10.1016/j.poly.2006.03.022
- Henderson R., Rothgery E. F., Schroeder H. A. Patent U. S. № 4496559. 1985.
- Patent CN. 104447532A. 2015.
- Askerov R.K., Magerramov A. M., Matsulevich Z. V. et al. // Russ. J. Coord. Chem. 2019. V. 45. P. 320. https://doi.org/10.1134/S1070328419030011
- Ninomiya M., Garud D. R., Koketsu M. // Coord. Chem. Rev. 2011. V. 255. P. 296. https://doi.org/10.1016/j.ccr.2011.07.009
- Garud D.R., Koketsu M., Ishihara H. et al. // Molecules. 2007. V. 2. P. 504. https://doi.org/10.3390/12030504
- Heimgartner H., Zhou Y., Plamen K. et. al. // Phosphorus, Sulfur, and Silicon and the Relat. Elem. 2008. V. 183. P. 840. https://doi.org/10.1080/10426500801898135
- Zakrzewski J., Huras B., Kiełczewska A. // Syn thesis. 2016. V. 48. P. 85. https://doi.org/10.1055/s-0035–1560481
- CrysAlisPro. Version 1.171.41.106a. Rigaku Oxford Diffraction, 2021.
- Sheldrick G. M. Acta Crystallogr. C. 2015. V. 71. P. 3. https://doi.org/10.1107/S2053229614024218
- Бацанов С.С. // Журн. неорган. химии. 1991. Т. 36. Вып. 12. С. 3015.
- Christoph J. // Dalton Trans. 2000. P. 3885. https://doi.org/10.1039/B003010O.
Қосымша файлдар
