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
DOI:
https://doi.org/10.18321/ectj1147Keywords:
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 structureAbstract
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
(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
(3). B. Sharifzadeh, N.O. Mahmoodi, M. Mamaghani, K. Tabatabaeian, A.S. Chirani, I. Nikokar, Bioorg. Med. Chem. Lett. 23 (2013) 548‒551. Crossref
(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
(5). V. Yu, K. Praliyev, A. Nagimova, A. Zazybin, Tetrahedron Lett. 56 (2015) 1631‒1634. Crossref
(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
(7). V. Nair, S. Vellalath, B.P. Babu, V. Varghese, R.R. Paula, E. Suresh, Org. Biomol. Chem. 8 (2010) 4861. Crossref
(8). А.G. Golikov, A.P. Kriven’ko, A.A. Bugaev, S. F. Solodovnikov, J. Struct. Chem. 47 (2006) 102‒105. Crossref
(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
(10). C. Pang, C. Sun, J. Wang, D. Xiao, L. Ding, H. Bu, Sci. China Chem. 56 (2013) 702–715. Crossref
(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
(13). Y. Eryanti, R. Hendra, T. Herlina, A. Zamri, U. Supratman, Procedia Chem. 17 (2015) 224–229. Crossref
(14). R.S. Rathore, S. Karthikeyan, Y. Alekhyak, K. Sathiyanarayanan, P.G. Aravindan, J. Chem. Sci. 123 (2011) 403–409. Crossref
(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
(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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