Abstract
The structures of six 2,2′-bipyridine derivatives containing aromatic amine moieties, namely N-aryl-4-aryl-1-(pyridin-2-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-3-amines, were studied by single-crystal X-ray diffraction. The molecular structures and the effect of the substituents of these compounds on the crystal packing are discussed.
References
E. C. Constable, C. E. Housecroft, Molecules, 2019, 24, 3951; DOI: https://doi.org/10.3390/molecules24213951.
C. Kaes, A. Katz, M. W. Hosseini, Chem. Rev., 2000, 100, 3553; DOI: https://doi.org/10.1021/cr990376z.
R. D. Hancock, Chem. Soc. Rev., 2013, 42, 1500; DOI: https://doi.org/10.1039/C2CS35224A.
J. C. Loren, J. S. Siegel, Angew. Chem., Int. Ed., 2001, 40, 754; DOI: https://doi.org/10.1002/1521-3773(20010216)40:4<754::AID-ANIE7540>3.0.CO;2-T.
V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. König, D. N. Kozhevnikov, Tetrahedron, 2008, 64, 8963; DOI: https://doi.org/10.1016/j.tet.2008.06.040.
M. Karnahl, S. Krieck, H. Görls, S. Tschierlei, M. Schmitt, J. Popp, D. Chartrand, G. S. Hanan, R. Groarke, J. G. Vos, S. Rau, Eur. J. Inorg. Chem., 2009, 4962; DOI: https://doi.org/10.1002/EJIC.200900310.
D. S. Kopchuk, N. V. Chepchugov, E. S. Starnovskaya, A. F. Khasanov, A. P. Krinochkin, S. Santra, G. V. Zyryanov, P. Das, A. Majee, V. L. Rusinov, V. N. Charushin, Dyes Pigm., 2019, 167, 151; DOI: https://doi.org/10.1016/j.dyepig.2019.04.029.
A. F. Khasanov, D. S. Kopchuk, I. L. Nikonov, O. S. Taniya, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, Russ. Chem. Bull., 2021, 70, 999; DOI: https://doi.org/10.1007/s11172-021-3179-2.
R. R. Harris, L. Black, S. Surapaneni, T. Kolasa, S. Majest, M. T. Namovic, G. Grayson, V. Komater, D. Wilcox, L. King, K. Marsh, M. F. Jarvis, M. Nuss, H. Nellans, L. Pruesser, G. A. Reinhart, B. Cox, P. Jacobson, A. Stewart, M. Coghlan, G. Carter, R. L. Bell, J. Pharmacol. Exp. Theor., 2004, 311, 904; DOI: https://doi.org/10.1124/JPET.104.070052.
R. Bakthavatchalam, C. A. Blum, H. Brielmann, T. M. Caldwell, S. de Lombaert, K. J. Hodgetts, X. Zheng, Patent WO 2004/55003 A1, 2004.
F. W. Goldberg, R. A. Ward, S. J. Powell, J. É. Debreczeni, R. A. Norman, N. J. Roberts, A. P. Dishington, H. J. Gingell, K. F. Wickson, A. L. Roberts, J. Med. Chem., 2009, 52, 7901; DOI: https://doi.org/10.1021/jm900807w.
M. R. Finlay, F. W. Goldberg, C. A. Roberts, N. J. Roberts, D. A. Rudge, Pat.US, 2009/048269 A1, 2009.
Y. Xing, J. Zuo, P. Krogstad, M. E. Jung, J. Med. Chem., 2018, 61, 1688; DOI: https://doi.org/10.1021/acs.jmedchem.7b01863.
B. Okram, T. Uno, Q. Ding, Y. Liu, Y. Jin, Q. Jin, X. Wu, J. Che, S. F. Yan, Patent WO 2009/097287, 2009.
E. Luepfert, Patent US2011/017203A1, 2011.
D. S. Kopchuk, N. V. Chepchugov, I. S. Kovalev, S. Santra, M. Rahman, K. Giri, G. V. Zyryanov, A. Majee, V. N. Charushin, O. N. Chupakhin, RSC Adv., 2017, 7, 9610; DOI: https://doi.org/10.1039/C6RA26305D.
E. S. Starnovskaya, Y. K. Shtaitz, A. P. Krinochkin, A. F. Khasanov, D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, AIP Conf. Proc., 2019, 2063, 040056; DOI: https://doi.org/10.1063/1.5087382.
D. S. Kopchuk, A. P. Krinochkin, E. S. Starnovskaya, Y. K. Shtaitz, A. F. Khasanov, O. S. Taniya, S. Santra, G. V. Zyryanov, A. Majee, V. L. Rusinov, O. N. Chupakhin, ChemistrySelect, 2018, 3, 4141; DOI: https://doi.org/10.1002/slct.201801167.
D. S. Kopchuk, E. S. Starnovskaya, Y. K. Shtaitz, A. F. Khasanov, G. A. Kim, E. V. Nosova, A. P. Krinochkin, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, Res. Chem. Intermediates, 2020, 46, 3929; DOI: https://doi.org/10.1007/s11164-020-04182-z.
A. Rammohan, G. M. Reddy, A. P. Krinochkin, D. S. Kopchuk, M. I. Savchuk, Y. K. Shtaitz, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, Synth. Commun., 2021, 51, 256; DOI: https://doi.org/10.1080/00397911.2020.1823993.
A. P. Krinochkin, M. R. Guda, D. S. Kopchuk, Ya. K. Shtaitz, K. V. Savateev, E. N. Ulomsky, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, Russ. J. Org. Chem., 2022, 58, 188; DOI: https://doi.org/10.1134/S1070428022020051.
A. P. Krinochkin, G. M. Reddy, D. S. Kopchuk, P. A. Slepukhin, Y. K. Shtaitz, I. A. Khalymbadzha, I. S. Kovalev, G. A. Kim, I. N. Ganebnykh, G. V. Zyryanov, O. N. Chupakhin, V. N. Charushin, Mendeleev Commun., 2021, 31, 542; DOI:https://doi.org/10.1016/j.mencom.2021.07.035.
O. C. Pfüeller, J. Sauer, Tetrahedron Lett., 1998, 39, 8821; DOI: https://doi.org/10.1002/chin.199908151.
S. P. Stanforth, B. Tarbit, M. D. Watson, Tetrahedron Lett., 2003, 44, 693; DOI: https://doi.org/10.1016/S0040-4039(02)02670-9.
A. M. Prokhorov, D. N. Kozhevnikov, Chem. Heterocycl. Compd., 2012, 48, 1153; DOI: https://doi.org/10.1007/s10593-012-1117-9.
V. N. Kozhevnikov, D. N. Kozhevnikov, T. V. Nikitina, V. L. Rusinov, O. N. Chupakhin, M. Zabel, B. König, J. Org. Chem., 2003, 68, 2882; DOI: https://doi.org/10.1021/jo0267955.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339; DOI: https://doi.org/10.1107/S0021889808042726.
G. M. Sheldrick, Acta Cryst., 2008, A64, 112; DOI: https://doi.org/10.1107/S0108767307043930.
Funding
This work was financially supported by the Russian Science Foundation (Project No. 21-13-00304) and the Council on Grants at the President of the Russian Federation (Project NSh-1223.2022.1.3). This work was performed using the equipment of the Joint Use Center “Spectroscopy and Analysis of Organic Compounds” (JUC SAOC) of the I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences V. I. Ovcharenko on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1533–1543, July, 2022.
No human or animal subjects were used in this research.
The authors declare no competing interests.
Rights and permissions
About this article
Cite this article
Slepukhin, P.A., Krinochkin, A.P., Starnovskaya, E.S. et al. Single-crystal X-ray diffraction analysis of arylamine-containing 2,2′-bipyridine derivatives. Russ Chem Bull 71, 1533–1543 (2022). https://doi.org/10.1007/s11172-022-3561-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-022-3561-8