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New Approaches to the Synthesis of 2,2′: 6′,2″-Terpyridine and Some of Its Derivatives

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Abstract

A new two-step procedure has been developed for the synthesis of 2,2′: 6′,2″-terpyridine and 4′-methylsulfanyl-2,2′: 6′,2″-terpyridine in more than 70% yield on the basis of Potts’ condensation. Efficient methods have been proposed for purification of all condensation products.

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References

  1. Morgan, S.G. and Burstall, F.H., J. Chem. Soc., 1932, no. 1, p.20.

    Article  Google Scholar 

  2. Allan, J.T.S., Quaranta, S., Ebralidze, I.I., Egan, J.G., Poisson, J., Laschuk, N.O., Gaspari, F., Easton, E.B., and Zenkina, O.V., ACS Appl. Mater. Interfaces, 2017, vol. 9, p. 40438.

    Article  CAS  PubMed  Google Scholar 

  3. Li, Z., Gu, J., Qi, S., Wu, D., Gao, L., Chen, Z., Guo, J., Li, X., Wang, Y., Yang, X., and Tu, Y., J. Am. Chem. Soc., 2017, vol. 139, p. 14364.

    Article  CAS  PubMed  Google Scholar 

  4. Elmas, S., Beelders, W., Bradley, S.J., Kroon, R., Laufersky, G., Andersson, M., and Nann, T., ACS Sustainable Chem. Eng., 2017, vol. 5, p. 10206.

    Article  CAS  Google Scholar 

  5. Berenblyum, A.S. and Al’-Vadkhav, Kh.A., Vestn. Mosk. Inst. Tonk. Khim. Tekhnol., 2010, no. 5, p.43.

    Google Scholar 

  6. Beletskaya, I.P., Bessmertnykh, A.G., and Guilard, R., Tetrahedron Lett., 1997, vol. 38, p. 2287.

    Article  CAS  Google Scholar 

  7. Duong, H.A., Wu, W., and Teo, Y.-Y., Organometallics, 2017, vol. 36, p. 4363.

    Article  CAS  Google Scholar 

  8. Heinemann, F., Karges, J., and Gasser, G., Acc. Chem. Res., 2017, vol. 50, p. 2727.

    Article  CAS  PubMed  Google Scholar 

  9. Mondal, D., Biswas, S., Paul, A., and Baitalik, S., Inorg. Chem., 2017, vol. 56, p. 7624.

    Article  CAS  PubMed  Google Scholar 

  10. Martínez, M.Á., Carranza, M.P., Massaguer, A., Santos, L., Organero, J.A., Aliende, C., de Llorens, R., Ng-Choi, I., Feliu, L., Planas, M., Rodríguez, A.M., Manzano, B.R., Espino, G., and Jalón, F.A., Inorg. Chem., 2017, vol. 56, p. 13679.

    Article  CAS  PubMed  Google Scholar 

  11. Hirahara, M., Nagai, S., Takahashi, K., Watabe, S., Sato, T., Saito, K., Yui, T., Umemura, Y., and Yagi, M., Inorg. Chem., 2017, vol. 56, p. 10235.

    Article  CAS  PubMed  Google Scholar 

  12. Matheu, R., Ertem, M.Z., Gimbert-Suriñach, C., Benet-Buchholz, J., Sala, X., and Llobet, A., ACS Catal., 2017, vol. 7, p. 6525.

    Article  CAS  Google Scholar 

  13. Jiang, J., Sherman, B.D., Zhao, Y., He, R., Ghiviriga, I., Alibabaei, L., Meyer, T.J., Leem, G., and Schanze, K.S., ACS Appl. Mater. Interfaces, 2017, vol. 9, p. 19529.

    Article  CAS  PubMed  Google Scholar 

  14. Kuehnel, M.F., Orchard, K.L., Dalle, K.E., and Reisner, E., J. Am. Chem. Soc., 2017, vol. 139, p. 7217.

    Article  CAS  PubMed  Google Scholar 

  15. Storrier, G.D. and Colbran, S.B., Inorg. Chim. Acta, 1999, vol. 284, p.76.

    Article  CAS  Google Scholar 

  16. Wang, S., Chu, W., Wang, Y., Liu, S., Zhang, J., Li, S., Wei, H., Zhou, G., and Qin, X., Appl. Organomet. Chem., 2013, vol. 27, p.373.

    Article  CAS  Google Scholar 

  17. Ashford, D.L., Song, W., Concepcion, J.J., Glasson, C.R.K., Brennaman, M.K., Norris, M.R., Fang, Z., Templeton, J.L., and Meyer, T.J., J. Am. Chem. Soc., 2012, vol. 134, p. 19189.

    Article  CAS  PubMed  Google Scholar 

  18. Winter, A., Egbe, D.A.M., and Schubert, U.S., Org. Lett., 2007, vol. 9, p. 2345.

    Article  CAS  PubMed  Google Scholar 

  19. Manzhelii, E.A., Cand. Sci. (Chem.) Dissertation, Moscow, 2014.

    Google Scholar 

  20. Harrison, D.P., Lapides, A.M., Binstead, R.A., Concepcion, J.J., Méndez, M.A., Torelli, D.A., Templeton, J.L., and Meyer, T.J., Inorg. Chem., 2013, vol. 52, p. 4747.

    Article  CAS  PubMed  Google Scholar 

  21. Wang, J.-L., Li, X., Shreiner, C.D., Lu, X., Moorefield, C.N., Tummalapalli, S.R., Medvetz, D.A., Panzner, M.J., Fronczek, F.R., Wesdemiotis, C., and Newkome, G.R., New J. Chem., 2012, vol. 36, p.484.

    Article  CAS  Google Scholar 

  22. Potts, K.T., Ralli, P., Theodoridis, G., and Winslow, P., Org. Synth., 1986, vol. 64, p.189.

    Article  CAS  Google Scholar 

  23. Potts, K.T., Ralli, P., Cipullo, M.J., and Theodoridis, G., J. Org. Chem., 1982, vol. 47, p. 3027.

    Article  CAS  Google Scholar 

  24. Potts, K.T., Usifer, D.A., Guadalupe, A., and Abruna, H.D., J. Am. Chem. Soc., 1987, vol. 109, p. 3961.

    Article  CAS  Google Scholar 

  25. Zhong, Y.-W., Yao, C.-J., and Nie, H.-J., Coord. Chem. Rev., 2013, vol. 257, p. 1357.

    Article  CAS  Google Scholar 

  26. Jameson, D.L. and Guise, L.E., Tetrahedron Lett., 1991, vol. 32, p. 1999.

    Article  CAS  Google Scholar 

  27. Park, H.-J. and Chung, Y.K., Dalton Trans., 2012, vol. 41, p. 5678.

    Article  CAS  PubMed  Google Scholar 

  28. Stefankiewicz, A.R., Walesa-Chorab, M., Harrowfield, J., Kubicki, M., Hnatejko, Z., Korabik, M., and Patroniak, V., Dalton Trans., 2013, vol. 42, p. 1743.

    Article  CAS  PubMed  Google Scholar 

  29. Santos, L.S., Rosso, G.B., Pilli, R.A., and Eberlin, M.N., J. Org. Chem., 2007, vol. 72, p. 5809.

    Article  CAS  PubMed  Google Scholar 

  30. https://www.sigmaaldrich.com/

  31. Becker, H.G.O., et al., Organikum. Organischchemisches Grundpraktikum, Weinheim: Wiley, 2004, 22nd edn. Translated under the title Organikum, Moscow: Mir, 2008, vol. 1, pp. 88, 92, 102,106.

    Google Scholar 

  32. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 443.

    Google Scholar 

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Authors and Affiliations

  1. Lomonosov Institute of Fine Chemical Technologies Moscow Technological University, pr. Vernadskogo 86, Moscow, 119571, Russia

    V. V. Zamalyutin, V. A. Bezdenezhnykh, A. I. Nichugovskiy & V. R. Flid

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  1. V. V. Zamalyutin
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  2. V. A. Bezdenezhnykh
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  3. A. I. Nichugovskiy
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  4. V. R. Flid
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Correspondence to V. V. Zamalyutin.

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Dedicated to Full Member of the Russian Academy of Sciences

I.P. Beletskaya on her jubilee

Original Russian Text © V.V. Zamalyutin, V.A. Bezdenezhnykh, A.I. Nichugovskiy, V.R. Flid, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 3, pp. 414–420.

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Zamalyutin, V.V., Bezdenezhnykh, V.A., Nichugovskiy, A.I. et al. New Approaches to the Synthesis of 2,2′: 6′,2″-Terpyridine and Some of Its Derivatives. Russ J Org Chem 54, 419–425 (2018). https://doi.org/10.1134/S1070428018030089

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  • DOI: https://doi.org/10.1134/S1070428018030089

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