Synthesis of 3-Alkyl-5-(diethylaminomethyl)-1-(1,3-thiazole)pyrazoles

A. R. Karayeva; Караева А. Р.; M. I. Shatirova; Шатирова М. И.; B. A. Mamedov; Мамедов Б. А.; Sh. F. Nagieva; Нагиева Ш. Ф.; L. I. Gadzhiyeva; Гаджиева Л. Я.

doi:10.31857/S0514749224010091

Synthesis of 3-Alkyl-5-(diethylaminomethyl)-1-(1,3-thiazole)pyrazoles

Authors: Karayeva A.R.¹, Shatirova M.I.¹, Mamedov B.A.¹, Nagieva S.F.¹, Gadzhiyeva L.I.¹
Affiliations:
1. Institute of Polymer Materials of Ministry of Science and Education of Republic of Azerbaijan
Issue: Vol 60, No 1 (2024)
Pages: 104-108
Section: Articles
URL: https://aspvestnik.ru/0514-7492/article/view/672246
DOI: https://doi.org/10.31857/S0514749224010091
EDN: https://elibrary.ru/EMXWFD
ID: 672246

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Abstract

By the reaction of 3-alkyl-5-(diethylaminomethyl) pyrazoles with chloroanhydride of monochloroacetic acid, the pyrazoles with chloromethyl carbonyl substituent have been synthesized. Due to presence of reactive COCH₂Cl groups in a molecule, the pyrazoles have been subjected to heterocyclization with thicarbamides (thiobenzamide, thicarbamide and phenylthiocarbamide) in the presence of triethyleamine in a medium of ethanol, as a result of which the previously unknown 3-alkyl-5-diethylaminomethyl-1-(1,3-thiazol)substituted pyrazole derivatives have been obtained.

Keywords

pyrazoles, thiocarbamides, thiazoles, heterocyclization, pharmacophore groups

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Hira A., Ameer F.Z., Sajjad A. J. Chil. Chem. Soc. 2020, 65 (1), 4746–4753. doi: 10.4067/S0717-97072020000104746
Khalifa M.E., Gobouri A.A., Kabli F.M., Altalhi T.A., Almalki A. S.A., Mohamed M.A. Molecules. 2018, 23 (12), 3285–3294. doi: 10.3390/molecules23123285
Dadiboyena S., Nefzi A. Eur. J. Med. Chem. 2011, 46 (11), 5258–5275. doi: 10.1016/j.ejmech.2011.09.016
Bandgar B.P., Gawande S.S., Bodade R.G., Gawande N.M. Khobragade, C.N. Bioorg. Med. Chem. 2009, 17 (24), 8168–8173. doi: 10.1016/j.bmc.2009.10.035
Abdellatif K.R.A., Fadaly W.A.A., Elshaier Y.A.M.M., Ali W.A.M., Kamel G.M. Bioorg. Chem. 2018, 77, 568–578. doi: 10.1016/j.bioorg.2018.02.018.
Hassan S.Y. Molecules. 2013, 18 (3), 2683–2711. doi: 10.3390/molecules18032683.
Кораблина Д.Д., Ворожцов Н.И., Свиридова Л.А., Каленикова Е.И., Медведев О.С. Хим.-фарм. ж. 2016, 50 (5), 3–18. [Korablina D.D., Vorozhtov N.I., Sviridova L.A., Kalenikova E.I., Medvedev O.S. Pharm. Chem. J. 2016, 50, 281–295.] doi: 10.30906/0023-1134-2016-50-5-3-18
Грапов А.Ф. Усп. хим. 1999, 68 (8), 773–784. [Gra-pov A.F. Russ. Chem. Rev. 1999, 68 (8), 697–707.] doi: 10.1070/RC1999v068n08ABEH000510
Машковский М.Д. Лекарственные средства, Москва: Новая волна, 2020, 16, 1216.
Jayanthi A., Anudurga G. Pesticide Biochem. Physiol. 2019, 155, 90–100. doi: 10.1016/j.pestbp.2019.01.011
Chong Shi, Chaowei Ma, Haojie Ma, Xioqiang Zhou, Jinhui Cao, Yuxing. Fan, Guosheng Huang. Tetrahedron. 2016, 72 (27–28), 4055–4058. doi: 10.1016/j.tet.2016.05.034
Abdalla M., Gomha S., Elaziz M.A., Serag N. Turk. J. Chem. 2016, 40, 441–453. doi: 10.3906/kim-1506-13
Samar S.T., Mengyao L., Abdelbasset A.F. Arkivoc. 2020, (i), 180–218. doi: 10.24820/ark.5550190.p011.308
Gomha S.M., Khalil K.D. Molecules. 2012, 17 (8), 9335–9347. doi: 10.3390/molecules17089335
Cukurovali A., Yilmaz I., Gur S., Kazaz C. Eur. J. Med. Chem. 2006, 41 (2), 201–207. doi: 10.1016/j.ejmech.2005.01.013
Hamad Elgazwy A.S., Nassar E., Zaki M.Y. Org. Chem. Curr. Ress., 2012, 1 (5), 112.
Hantzsch A., Weber J.H. Beric. Deuts. Chem. Gesell. 1887, 20 (2), 3118–3132. doi: 10.1002/cber.188702002200
Hamed F.I., Mohamed A.A., Abouzied A.S. OALib. J. 2017, 4 (5), 1–14. doi: 10.4236/oalib.1103526
Гаджилы Р.А., Дикусар Е.А., Алиев А.Г., Караева А.Р., Нагиева Ш.Ф., Поткин В.И. ЖОрХ. 2015, 51 (4), 547–550. [Gadzhili R.A., Dikusar E.A., Aliev A.K., Karaeva A.R., Nagieva Sh.F., Potkin V.I. Russ. J. Org. Chem. 2015, 51 (4), 530–533.] doi: 10.1134/S1070428015040120
Karayeva A.R. Chem. Prob. 2019, 4 (17), 584. doi: 10.32737/2221-8688-2019-4-584-590
Гаджилы Р.А., Алиев А.Г., Караева А.Р., Нагиева Ш.Ф. Третья всероссийская научная конференция “Успехи синтеза и комплексообразования”, 21–25 апреля, Москва, 2014, часть 1, 103.