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Russian Journal of General Chemistry

, Volume 86, Issue 12, pp 2887–2890 | Cite as

Highly efficient synthesis of quinoxaline derivatives catalized by iridium complex

  • D. LvEmail author
  • Z. Xie
  • B. Gu
  • H. Wu
  • H. Wan
Article

Abstract

A novel iridium complex was used to catalyze a mild reaction of phenylenediamine with propanediol that led to formation of quinoxaline derivatives with moderate to high yields. The reaction diemonstrated strong compatibility with substrates bearing various functional groups.

Keywords

phenylenediamine propanediol quinoxaline derivatives iridium complex 

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References

  1. 1.
    Seitz, L.E., Suling, W.J., and Reynolds, R.C., J. Med. Chem., 2002, vol. 45, p. 5604. doi 10.1021/jm020310nCrossRefGoogle Scholar
  2. 2.
    Loriga, M., Piras, S., Sanna, P., and Paglietti, G., Farmaco, 1997, vol. 52, p. 157.PubMedGoogle Scholar
  3. 3.
    He, W., Meyers, M.R., Hanney, B., Spada, A., Blider, G., Galzeinski, H., Amin, D., Needle, S., Page, K., Jayyosi, Z., and Perrone, H., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 3097. doi 10.1016/S0960-894X(03)00655-3CrossRefGoogle Scholar
  4. 4.
    Kim, Y.B., Kim, Y.H., Park, J.Y., and Kim, S.K., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 541. doi 10.1016/j.bmcl.2003.09.086CrossRefGoogle Scholar
  5. 5.
    Lindsley, C.W., Zhao, Z., Leister, W.H., Robinson, R.G., Barnett, S.F., Defeojones, D.J., Jones, E., Hartman, G.D., Huff, J.R., Huber, H.E., and Duggan, M.E., Bioorg. Med. Chem. Lett., 2005,vol. 15, p. 761. doi 10.1016/j.bmcl.2004.11.011CrossRefGoogle Scholar
  6. 6.
    Peter, P.C., Gang, Z., Grace, A.M., Carlos, H., and Linda, M.G., J. Org. Lett., 2004, vol. 6, p. 333. doi 10.1021/ol036045xCrossRefGoogle Scholar
  7. 7.
    Sonawane, N.D. and Rangnekar, D.W., J. Heterocycl. Chem., 2002, vol. 39, p. 303. doi 10.1002/jhet.5570390210CrossRefGoogle Scholar
  8. 8.
    Katoh, A., Yoshida, T., and Ohkanda, J., Heterocycles, 2000, vol. 52, p. 911. doi 10.3987/COM-99-S61CrossRefGoogle Scholar
  9. 9.
    Dailey, S., Feast, J.W., Peace, R.J., Sage, I.C., Till, S., and Wood, E.L., J. Mater. Chem., 2001, vol. 11, p. 2238. doi 10.1039/b104674hCrossRefGoogle Scholar
  10. 10.
    O’Brien, D., Weaver, M.S., Lidzey, D.G., and Bradley, D.D.C., Appl. Phys. Lett., 1996, vol. 69, p. 881. doi 10.1021/ja0273750CrossRefGoogle Scholar
  11. 11.
    Jonathan, L.S., Hiromitsu, M., Toshihisa, M., Vincent, M.L., and Hiroyuku, F., J. Am. Chem. Soc., 2002, vol. 124, p. 13474.CrossRefGoogle Scholar
  12. 12.
    Furniss, B.S., Hannafort, A.J., Smith, P.W.G., and Tatchell, A.R., Vogel’s Textbook of Practical Organic Chemistry, New York: Wiley, 5nd ed., 1978, p. 1190.Google Scholar
  13. 13.
    Bhosale, R.S., Sarda, S.R., Ardhapure, S.S., Jadhav, W.N., Bhusare, S.R., and Pawar, R.P., Tetrahedron Lett., 2005, vol. 46, p. 7183. doi 10.1016/j.tetlet.2005.08.080CrossRefGoogle Scholar
  14. 14.
    Huang, T.K., Wang, R., Shi, L., and Lu, X.X., Catal. Comm., 2008, vol. 9, p. 1143. doi 10.1016/j.catcom.2007.10.024CrossRefGoogle Scholar
  15. 15.
    Heravi, M.M., Bakhtiari, K.H., Bamoharram, F.F., and Tehrani, M.H., Montasch. Chem., 2007, vol. 138, p. 465. doi 10.1007/s00706-007-0594-5CrossRefGoogle Scholar
  16. 16.
    Robinson, R.S. and Taylor, R.J.K., Synlett., 2005, vol. 6, p. 1003. doi 10.1055/s-2005-864830Google Scholar
  17. 17.
    Raw, S.A., Wilfred, C.D., and Taylor, R.J.K., Org. Biomol. Chem., 2004, vol. 2, p. 788. doi 10.1039/b315689cCrossRefGoogle Scholar
  18. 18.
    Raw, S.A., Wilfred, C.D., and Taylor, R.J.K., Chem. Commun, 2003, vol. 10, p. 2286. doi 10.1039/b307177bCrossRefGoogle Scholar
  19. 19.
    Brewster, T.P., Miller, A.J.M., Heinekey, D.M., and Goldberg, K.I., J. Am. Chem. Soc., 2013, vol. 135, p. 16022. doi 10.1002/adsc.200600638CrossRefGoogle Scholar
  20. 20.
    Hamid, M.H.S.A., Slatford, P.A., and Williams, J.M.J., Adv. Synth. Catal., 2007, vol. 349, p. 1555. doi 10.1002/adsc.200600638CrossRefGoogle Scholar
  21. 21.
    Guillena, G., Ramón D.J., and Yus, M., Angew. Chem. Int. Ed., 2007, vol. 46, p. 2358. doi 10.1002/anie.200603794CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  1. 1.School of Chemical and Material EngineeringJiangnan UniversityWuxi, Jiangsu ProvinceChina
  2. 2.Huzhou Entry-Exit Inspection and Quarantine BureauHuzhouChina

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