Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl- 3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Authors

  • Zh.A. Koshetova A.B. Bekturov Institute of Chemical Sciences, 106, Ualikhanov str., Almaty, Kazakhstan; Kazakh National Women’s Teacher Training University, 99, Ayteke bi str., Almaty, Kazakhstan
  • V.K. Yu A.B. Bekturov Institute of Chemical Sciences, 106, Ualikhanov str., Almaty, Kazakhstan
  • T.K. Iskakova A.B. Bekturov Institute of Chemical Sciences, 106, Ualikhanov str., Almaty, Kazakhstan
  • N.A. Zhumanova A.B. Bekturov Institute of Chemical Sciences, 106, Ualikhanov str., Almaty, Kazakhstan; Kazakh National Women’s Teacher Training University, 99, Ayteke bi str., Almaty, Kazakhstan
  • K.M. Beketov A.B. Bekturov Institute of Chemical Sciences, 106, Ualikhanov str., Almaty, Kazakhstan
  • A.E. Malmakova A.B. Bekturov Institute of Chemical Sciences, 106, Ualikhanov str., Almaty, Kazakhstan
  • K.D. Praliyev A.B. Bekturov Institute of Chemical Sciences, 106, Ualikhanov str., Almaty, Kazakhstan
  • T.M. Seilkhanov Sh. Ualikhanov State University, 76, Abai str., Kokshetau, Kazakhstan
  • K.D. Berlin Oklahoma State University, Stillwater, 74078, USA

DOI:

https://doi.org/10.18321/ectj1147

Keywords:

7-arylidene-3,3a,4,5,6,7-(hexa¬hydro-5-(2-ethoxyethyl)-2-phe¬nyl-3-aryl-2H-pyrazolo[4,3-c] pyridine, heterocyclisation, X-ray crystal structure

Abstract

A Claisen-Schmidt type reaction of 1-(2-ethoxyethyl)piperidin-4-one with differ­ent aromatic aldehydes led to corresponding dienones with a yield of 65‒71%. 7-Arylidene-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridines were synthesized by heterocyclization of 3,5-dia­rylidene-piperidin-4-ones with phenylhydrazine hydrochloride in methanol at 70 °C over 4‒6 h. The X-ray crystal structure determination of 7-(p-methoxy­benzyliden)-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-(p-methoxy­phenyl)-2H-pyrazolo[4,3-c]pyridine hydrochloride (the deposition number is CCDC 862410) was completed. The piperidine and pyrazoline rings are close to a chair and envelope conformations, respectively.

 

References

(1). J. Krapcho, C.F. Turk. J. Med. Chem. 22 (1979) 207‒210. Crossref DOI: https://doi.org/10.1021/jm00188a018

(2). B. Insuasty, A. Montoya, D. Becerra, J. Quiroga, R. Abonia, S. Robledo, I.D. Vélez, Y. Upegui, M. Nogueras, J. Cobo, European J. Med. Chem. 67 (2013) 252‒262. Crossref DOI: https://doi.org/10.1016/j.ejmech.2013.06.049

(3). B. Sharifzadeh, N.O. Mahmoodi, M. Mamaghani, K. Tabatabaeian, A.S. Chirani, I. Nikokar, Bioorg. Med. Chem. Lett. 23 (2013) 548‒551. Crossref DOI: https://doi.org/10.1016/j.bmcl.2012.11.024

(4). V.K. Yu, A.Zh. Kabdraissova, K.D. Praliyev, S.N. Shin, K.D. Berlin, J. Saudi Chem. Soc. 13 (2009) 209‒217. Crossref DOI: https://doi.org/10.1016/j.jscs.2009.04.001

(5). V. Yu, K. Praliyev, A. Nagimova, A. Zazybin, Tetrahedron Lett. 56 (2015) 1631‒1634. Crossref DOI: https://doi.org/10.1016/j.tetlet.2015.02.001

(6). S.S. Zhumakova, A.E. Malmakova, V.K. Yu, K.D. Praliev, T.K. Iskakova, A.Yu. Ten, M.K. Amirkulova, D.M. Kadyrova, E.M. Satpaeva, T.M. Seilkhanov, Pharm. Chem. J. 54 (2021) 1209‒1214. Crossref DOI: https://doi.org/10.1007/s11094-021-02345-9

(7). V. Nair, S. Vellalath, B.P. Babu, V. Varghese, R.R. Paula, E. Suresh, Org. Biomol. Chem. 8 (2010) 4861. Crossref DOI: https://doi.org/10.1039/c0ob00180e

(8). А.G. Golikov, A.P. Kriven’ko, A.A. Bugaev, S. F. Solodovnikov, J. Struct. Chem. 47 (2006) 102‒105. Crossref DOI: https://doi.org/10.1007/s10947-006-0273-0

(9). B.K. Sagar, K.B. Harsha, H.S. Yathirajan, K.S. Rangappa, R.S. Rathore, C. Glidewell, Acta Cryst. 73 (2017) 298–304. Crossref DOI: https://doi.org/10.1107/S205322961700273X

(10). C. Pang, C. Sun, J. Wang, D. Xiao, L. Ding, H. Bu, Sci. China Chem. 56 (2013) 702–715. Crossref DOI: https://doi.org/10.1007/s11426-013-4840-x

(11). E. McDonald, P.N. Horton, M.B. Hursthouse (2007) University of Southampton, Crystal Structure Report Archive. Crossref

(12). F.H. Allen, O. Kennard, D.G. Warson, L. Brammer, A.G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2 (1987) S1-S18. Crossref DOI: https://doi.org/10.1039/p298700000s1

(13). Y. Eryanti, R. Hendra, T. Herlina, A. Zamri, U. Supratman, Procedia Chem. 17 (2015) 224–229. Crossref DOI: https://doi.org/10.1016/j.proche.2015.12.136

(14). R.S. Rathore, S. Karthikeyan, Y. Alekhyak, K. Sathiyanarayanan, P.G. Aravindan, J. Chem. Sci. 123 (2011) 403–409. Crossref DOI: https://doi.org/10.1007/s12039-011-0091-6

(15). B.N. Tarasevich, Moskva: Izd. MGU (2012) 55. [in Russian]. Web-Page

(16). G.M. Sheldrick, Acta Cryst. A 64 (2008) 112– 122. Crossref DOI: https://doi.org/10.1107/S0108767307043930

(17). Patent KZ 10436. K.D. Praliyev, V.K. Yu, T.K. Iskakova, N.A. Ismagulova et al. Bull. #12, 2004.

(18). Preliminary patent KZ 10435. K.D. Praliyev, T.K. Iskakova, V.K. Yu, S.N. Shin, N.A. Ismagulova et al. Bull. #7, 2001.

(19). Preliminary patent KZ 11197. T.K. Iskakova, K.D. Praliyev, N.A. Ismagulova, V.K. Yu, S.N. Shin et al. Bull. #2, 2002.

(20). V.K. Yu, L.K. Bahtybayeva, A.Yu. Ten, A.E. Malmakova, Proceedings of XXI Int. Conf. Sci. Techn. ‒ Russia-Korea-CIS, (2021), Moscow, 242.

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Published

31-03-2022

How to Cite

Koshetova, Z., Yu, V., Iskakova, T., Zhumanova, N., Beketov, K., Malmakova, A., … Berlin, K. (2022). Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl- 3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure. Eurasian Chemico-Technological Journal, 24(1), 43–50. https://doi.org/10.18321/ectj1147

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