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Synthesis of azinyl azolyl pyrimidines as new hybrid N,N,N-tridentate ligands for coordination chemistry

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Chemistry of Heterocyclic Compounds Aims and scope

Routes were proposed for the synthesis of new pyrimidine-derived polycyclic nitrogen heterocycles – 4-(1H-pyrazol-1-yl)-2-(pyridin- 2-yl)pyrimidines with various donor substituents, isomeric 2-(1H-pyrazol-1-yl)-4-(pyridin-2-yl)pyrimidines, 2-(pyrazin-2-yl)-4-(1Hpyrazol- 1-yl)pyrimidines, and 4-(1H-pyrazol-1-yl)-2-(pyrimidin-2-yl)pyrimidines – which are of interest as N,N,N-tridentate ligands for the synthesis of transition metal coordination compounds. Experimental and theoretical studies of the electronic structure of the resulting compounds were carried out.

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References

  1. (a) Constable, E. C. Chem. Soc. Rev. 2007, 36, 246. (b) Constable, E. C. Coord. Chem. Rev. 2008, 252, 842. (c) Eryazici, I.; Moorefield, C. N.; Newkome, G. R. Chem. Rev. 2008, 108, 1834. (d) Wild, A.; Winter, A.; Schlütter, F.; Schubert, U. S. Chem. Soc. Rev. 2011, 40, 1459. (e) Vyalba, F. Y.; Ivantsova, A. V.; Zhdanova, K. A.; Usachev, M. N.; Gradova, M. A.; Bragina, N. A. Mendeleev Commun. 2022, 32, 675. (f) Filyakova, V. I.; Boltacheva, N. S.; Pervova, M. G.; Charushin, V. N. Mendeleev Commun. 2021, 31, 388. (g) Salimova, I. O.; Berezina, A. V.; Moiseeva, A. A.; Zyk, N. V.; Beloglazkina, E. K. Russ. Chem. Bull. 2022, 71, 267.

  2. (a) Halcrow, M. A. New J. Chem. 2014, 38, 1868. (b) Halcrow, M. A. Coord. Chem. Rev. 2005, 249, 2880. (c) Halcrow, M. A. Coord. Chem. Rev. 2009, 253, 2493. (d) Olguín, J.; Brooker, S. Coord. Chem. Rev. 2011, 255, 203. (e) Cheprakova, E. M.; Verbitsky, E. V.; Kiskin, M. A.; Aleksandrov, G. G.; Slepukhin, P. A.; Sidorov, A. A.; Starichenko, D. V.; Shvachko, Y. N.; Eremenko, I. L.; Rusinov, G. L.; Charushin, V. N. Polyhedron 2015, 100, 89. (f) Zhilina E. F.; Chizhov, D. L.; Sidorov, A. A.; Aleksandrov, G. G.; Kiskin, M.; Slepukhin P. A.; Fedin, M.; Starichenko, D. V.; Korolev, A. V.; Shvachko, Y. N.; Eremenko, I. L.; Charushin, V. N. Polyhedron 2013, 53, 122. (g) Khmara, E. F.; Chizhov, D. L.; Sidorov, A. A.; Aleksandrov, G. G.; Slepukhin, P. A.; Kiskin, M. A.; Tokarev, K. L.; Filyakova, V. I.; Rusinov, G. L.; Smolyaninov, I. V.; Bogomyakov, A. S.; Starichenko, D. V.; Shvachko, Y. N.; Korolev, A. V.; Eremenko, I. L.; Charushin, V. N. Russ. Chem. Bull. 2012, 61, 313.

  3. (a) Verbitskiy, E. V.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Synthesis 2018, 193. (b) Lipunova, G. N.; Nosova, E. V.; Charushin, V. N.; Chupakhin, O. N. Curr. Org. Synth. 2018, 15, 793. (c) Dinastiya, E. M.; Verbitsky E. V.; Gadirov, R. M.; Samsonova. L. G.; Degtyarenko, K. M.; Grigoryev, D. V.; Kurtcevich, A. E., Solodova, T. A.; Tel'minov, E. N.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. J. Photochem. Photobiol. A: Chem. 2021, 408, 113089. (d) Verbitsky, E. V.; Dinastiya, E. M.; Baranova, A. A.; Khokhlov, K. O.; Chuvashov, R. D.; Yakovleva, Y. A.; Makarova, N. I.; Vetrova, E. V.; Metelitsa, A. V.; Slepukhin, P. A.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Dyes Pigm. 2018, 159, 35. (e) Verbitskiy, E. V.; Baranova, A. A.; Khokhlov, K. O.; Yakovleva, Y. A.; Chuvashov, R. D.; Kim, G. A.; Moiseykin, E. V.; Dinastiya, E. M.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Chem. Heterocycl. Compd. 2018, 54, 604.

  4. (a) Almond-Thynne, J.; Blakemore, D. C.; Pryde, D. C.; Spivey, A. C. Chem. Sci. 2017, 8, 40. (b) Rossi, R.; Bellina, F.; Lessi, M. Adv. Synth. Catal. 2012, 354, 1181. (c) Rewcastle, G. W. In Comprehensive Heterocyclic Chemistry III; Aitken, A., Ed.; Elsevier: Amsterdam, 2008, vol. 8, p. 117. (d) Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036. (e) Schröter, S.; Stock, C.; Bach, T. Tetrahedron. 2005, 61, 2245. (f) Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125. (g) Parry, P. R.; Wang, C.; Batsanov, A. S; Bryce, M. R.; Tarbit, B. J. Org. Chem. 2002, 67, 7541. (h) Dolšak, A.; Mrgole, K.; Sova, M. Catalysts 2021, 11, 439. (i) Khan, I.; Khalid, M.; Adeel, M.; Khan, M. U.; Khan, M. S.; Ahmad, N.; Ali, A.; Akram, M. Optik 2020, 219, 165285. (j) Kim, J.; Cho, Y. S.; Min, S.-J. Bull. Kor. Chem. Soc. 2016, 37, 1998. (k) Xu, C.; Li, H.; Wang, Z.; Lou, X.; Fu, W. Monatsh. Chem. 2014, 145, 767. (l) Martínez, M. M.; Pérez-Caaveiro, C.; Peña-López, M.; Sarandeses, L. A.; Perez Sestelo, J. Org. Biomol. Chem. 2012, 10, 9045. (m) Sengmany, S.; Le Gall, E.; Léonel, E. Molecules 2011, 16, 5550. (n) Wang, X.; Sathunuru, R.; Melendez,V.; Kozar, M. P.; Lin, A. J. J. Heterocycl. Chem. 2010, 47, 1056. (o) Hussain, M.; Hung, N. T.; Khera, R. A.; Malik, I.; Zinad, D. S.; Langer, P. Adv. Synth. Catal. 2010, 352, 1429. (p) Tumkevicius, S.; Dodonova, J.; Baskirova, I.; Voitechovicius, A. J. Heterocycl. Chem. 2009, 46, 960. (q) Gholap, A. R.; Toti, K. S.; Shirazi, F.; Deshpande, M. V.; Srinivasan, K. V. Tetrahedron 2008, 64, 10214. (r) Colombo, M.; Giglio, M.; Peretto, I. J. Heterocycl. Chem. 2008, 45, 1077. (s) Conde Ceide, S.; Garrido Montalban, A. Tetrahedron Lett. 2006, 47, 4415. (t) Delia, T. J.; Schomaker, J. M.; Kalinda, A. S. J. Heterocycl. Chem. 2006, 43, 127. (u) Boully, L.; Turck, A.; Plé, N.; Darabantu, M. J. Heterocycl. Chem. 2005, 42, 1423. (v) Zhou, B.; Taylor, B.; Kornau, K. Tetrahedron Lett. 2005, 46, 3977. (w) Feuerstein, M.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2003, 687, 327. (x) Qing, F.-l.; Wang, R.; Li, B.; Zheng, X.; Meng, W.-D. J. Fluorine Chem. 2003, 120, 21. (y) Walsh, K.; Sneddon, H. F.; Moody, C. J. ChemSusChem 2013, 6, 1455. (z) Lee, M.; Rucil, T.; Hesek, D.; Oliver, A. G.; Fisher, J. F.; Mobashery, S. J. Org. Chem. 2015, 80, 7757.

  5. Slee, D. H.; Chen, Y.; Zhang, X.; Moorjani, M.; Lanier, M. C.; Lin, E.; Rueter, J. K.; Williams, J. P.; Lechner, S. M.; Markison, S.; Malany, S.; Santos, M.; Gross, R. S.; Jalali, K.; Sai, Y.; Zuo, Z.; Yang, C.; Castro-Palomino, J. C.; Crespo, M. I.; Prat, M.; Gual, S.; Diaz, J.-L.; Saunders, J. J. Med. Chem. 2008, 51, 1719.

    Article  CAS  PubMed  Google Scholar 

  6. Bushuev, M. B.; Gatilov, Y. V.; Krivopalov, V. P.; Nikolaenkova, E. B. J. Coord. Chem. 2012, 65, 550.

    Article  CAS  Google Scholar 

  7. Bushuev, M. B.; Krivopalov, V. P.; Nikolaenkova, E. B.; Daletsky, V. A.; Berezovskii, G. A.; Sheludyakova, L. A.; Varnek, V. A. Polyhedron. 2012, 43, 81.

    Article  CAS  Google Scholar 

  8. Bushuev, M. B.; Gatilov, Y. V.; Nikolaenkova, E. B.; Vasiliev, V. G.; Krivopalov, V. P. Inorg. Chim. Acta. 2013, 395, 95.

    Article  CAS  Google Scholar 

  9. Bushuev, M. B.; Pishchur, D. P.; Logvinenko, V. A.; Gatilov, Y. V.; Korolkov, I. V.; Shundrina, I. K.; Nikolaenkova, E. B.; Krivopalov, V. P. Dalton Trans. 2016, 45, 107.

    Article  CAS  PubMed  Google Scholar 

  10. Bushuev, M. B.; Vinogradova, K. A.; Gatilov, Y. V.; Korolkov, I. V.; Nikolaenkova, E. B.; Krivopalov, V. P. Inorg. Chim. Acta. 2017, 467, 238.

    Article  CAS  Google Scholar 

  11. Bushuev, M. B.; Krivopalov, V. P.; Nikolaenkova, E. B.; Vinogradova, K. A.; Gatilov, Y. V. Dalton Trans. 2018, 47, 9585.

    Article  CAS  PubMed  Google Scholar 

  12. Brown, D. J.; Cowden, W. B.; Grigg, G. W.; Kavulak, D. Aust. J. Chem. 1980, 33, 2291.

    Article  CAS  Google Scholar 

  13. Zhao, Q.; Huang, W.; Lin, W.; Liu, S.; Xu, W. CN Patent 103936795.

  14. Caton, MP L.; Hurst, D. T.; McOmie, J. F. W.; Hunt, R. R. J. Chem. Soc. C 1967, 1204.

  15. Medwid, J. B.; Paul, R.; Baker, J. S.; Brockman, J. A.; Du, M. T.; Hallet, W. A.; Hanifin, J. W.; Hardy, R. A., Jr.; Tarrant, M. E.; Torley, L. W.; Wrenn, S. J. Med. Chem. 1990, 33, 1230.

    Article  CAS  PubMed  Google Scholar 

  16. Lafferty, J. J.; Case, F. H. J. Org. Chem. 1967, 32, 1591.

    Article  CAS  Google Scholar 

  17. Nikolaenkova, E. B.; Krivopalov, V. P. Chem. Heterocycl. Compd. 1997, 33, 968.

    Article  CAS  Google Scholar 

  18. Hanyu, N.; Saito, T.; Slibata, T.; Sato, K.; Ogino, K. WO Patent 2009099192.

  19. Hanyu, N.; Saito, T.; Slibata, T.; Sato, K.; Ogino, K. WO Patent 2009099193.

  20. Flores, A. F. C.; Pizzuti, L.; Brondani, S.; Rossato, M.; Zanatto, N.; Martins, M. A. P. J. Braz. Chem. Soc. 2007, 18, 1316.

    Article  CAS  Google Scholar 

  21. Danagulyan, G. G.; Mkrtchyan, A. D. Khim. Zh. Armenii 2005, 58(1-2), 70.

    CAS  Google Scholar 

  22. Brown, D. J.; Cowden, W. B. Aust. J. Chem. 1982, 35, 1203.

    Article  CAS  Google Scholar 

  23. Duerrenberger, F.; Burckhardt, S.; Geisser, P. O.; Buhr, W.; Funk, F.; Bainbridge, J. M.; Corden, V. A.; Courtney, S. M.; Davenport, T.; Jaeger, S.; Ridgill, M. P.; Slack, M.; Yarnold, C. J.; Yau, W. T. US Patent 2012202806.

  24. Cai, S. X.; Drewe, J. A.; Nguyen, B.; Reddy, P. S.; Pervin, A. WO Patent 2002047690

  25. Sleebs, B. E.; Street, I. P.; Bu, X.; Baell, J. B. Synthesis 2010, 1091.

  26. Csihony, S.; Mika, L. T.; Vlad, G.; Barta, K.; Mehnert, C. P.; Horvath, I. T. Collect. Czech. Chem. Commun. 2007, 72, 1094.

    Article  CAS  Google Scholar 

  27. Strotmeyer, K. P.; Fritsky, I. O.; Ott. R.; Pritzkow, H.; Kramer, R. Supramol. Chem. 2003, 15, 529.

    Article  CAS  Google Scholar 

  28. Kinigopoulou, M.; Filippidou, M.; Gogou, M.; Giannousi, A.; Fouka, P.; Ntemou, N.; Alivertis, D.; Georgis, C.; Brentas, A.; Polychronidou, V.; Voulgari, P.; Theodorou, V.; Skobridis, K. RSC Adv. 2016, 6, 61458.

    Article  CAS  Google Scholar 

  29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams-Young, D.; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; Foresman, J. B.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, 2016.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russia

    Elena B. Nikolaenkova & Victor P. Krivopalov

  2. Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 3 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russia

    Nikita A. Shekhovtsov & Mark B. Bushuev

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  1. Elena B. Nikolaenkova
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  2. Nikita A. Shekhovtsov
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  3. Mark B. Bushuev
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  4. Victor P. Krivopalov
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Correspondence to Elena B. Nikolaenkova or Mark B. Bushuev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(9/10), 672–684

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Nikolaenkova, E.B., Shekhovtsov, N.A., Bushuev, M.B. et al. Synthesis of azinyl azolyl pyrimidines as new hybrid N,N,N-tridentate ligands for coordination chemistry. Chem Heterocycl Comp 59, 672–684 (2023). https://doi.org/10.1007/s10593-023-03253-4

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