Research on Chemical Intermediates

, Volume 39, Issue 4, pp 1907–1916 | Cite as

An efficient and convenient one-pot multicomponent synthesis of novel pyrimidine derivatives: N-(4-aryl-6-(pyridin-2-yl)pyrimidin-2-yl)cyanamides

  • Liangce Rong
  • Xianyong Wei
  • Shimin Tao
  • Yao Lu
  • Ruilun Xie
  • Jun Zhou
  • Zhimin Zong


An efficient and facile synthesis of novel pyrimidine derivatives, N-(4-aryl-6-(pyridin-2-yl)pyrimidin-2-yl)cyanamides, via one-pot multicomponent reaction of different aromatic aldehydes, 2-acetylpyridine, and cyanoguanidine in the presence of NaOH in anhydrous EtOH is reported. Pyrimidine derivatives are extremely important six membered aromatic heterocyclic rings containing two nitrogen atoms which have a wide variety of important biologically activity. This method has the advantages of easy work-up, convenient purification, short reaction times, and high yields.


Multicomponent reaction N-((Pyridin-2-yl)pyrimidin-2-yl)cyanamide 2-Acetylpyridine Cyanoguanidine Synthesis 



This work was supported by National Natural Science Foundation of China (NSFC) (21172188), Foundation of Xuzhou Normal University (10XLS02) and Priority Academic Program Development of Jiangsu Higher Education Institutions.


  1. 1.
    R.V.A. Orru, M. de Greef, Synthesis 2003, 1471 (2003)CrossRefGoogle Scholar
  2. 2.
    S. Brase, C. Gil, K. Knepper, Bioorg. Med. Chem. 10, 2415 (2002)CrossRefGoogle Scholar
  3. 3.
    A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)CrossRefGoogle Scholar
  4. 4.
    D. Strubing, H. Neumann, S. Klaus, S. Hubner, M. Beller, Tetrahedron 61, 11333 (2005)CrossRefGoogle Scholar
  5. 5.
    V. Nair, A.U. Vinod, C. Rajesh, J. Org. Chem. 66, 4427 (2001)CrossRefGoogle Scholar
  6. 6.
    J.F. Cheng, M. Chen, T. Arrhenius, A. Nadzen, Tetrahedron Lett. 43, 6293 (2002)CrossRefGoogle Scholar
  7. 7.
    M. Egli, P.S. Pallan, C.R. Allerson, T.P. Prakash, A. Berdeja, J.H. Yu, S. Lee, A. Watt, H. Gaus, B. Bhat, E.E. Swayze, P.P. Seth, J. Am. Chem. Soc. 133, 16642 (2011)CrossRefGoogle Scholar
  8. 8.
    M.M. Gonzalez, M. Vignoni, M. Pellon-Maison, M.A. Ales-Gandolfo, M.R. Gonzalez-Baro, R. Erra-Balsells, B. Epe, F.M. Cabrerizo, Org. Biomol. Chem. 10, 1807 (2012)CrossRefGoogle Scholar
  9. 9.
    P. Jansa, O. Hradil, O. Baszczyňski, M. Dračínský, B. Klepetářová, A. Holý, J. Balzarini, Z. Janeba, Tetrahedron 68, 865 (2012)CrossRefGoogle Scholar
  10. 10.
    J. Romanowska, M. Sobkowski, A. Szymanska-Michalak, K. Kolodziej, A. Dabrowska, A. Lipniacki, A. Piasek, Z.M. Pietrusiewicz, M. Figlerowicz, A. Guranowski, J. Boryski, J. Stawinski, A. Kraszewski, J. Med. Chem. 54, 6482 (2011)CrossRefGoogle Scholar
  11. 11.
    B. Crescenzi, O. Kinzel, E. Muraglia, F. Orvieto, G. Pescatore, M. Rowley, V. Summa, WO 2004058757, 2004. Chem. Abstr. 141,123648 (2004)Google Scholar
  12. 12.
    R. Ramajayam, N.B. Mahera, N. Neamati, M.R. Yadav, R. Giridhar, Archiv der Pharmazie, vol. 342 (Weinheim, Germany, 2009), p. 710Google Scholar
  13. 13.
    J.R. Bertino, J. Clin. Oncol. 11, 5 (1993)Google Scholar
  14. 14.
    V.A. Chebanov, Y.I. Sakhno, S.M. Desenko, Ultrason. Sonochem. 19, 707 (2012)CrossRefGoogle Scholar
  15. 15.
    Y. Kawakita, H. Banno, T. Ohashi, T. Tamura, T. Yusa, A. Nakayama, H. Miki, H. Iwata, H. Kamiguchi, T. Tanaka, N. Habuka, S. Sogabe, Y. Ohta, T. Ishikawa, J. Med. Chem. 55, 3975 (2012)CrossRefGoogle Scholar
  16. 16.
    E.I. Klimova, J.J. Sanchez García, T. Klimova, T.R. Apan, E.A. Vázquez López, M. Flores-Alamo, M.M. García, J. Organomet. Chem. 708, 37 (2012)CrossRefGoogle Scholar
  17. 17.
    O.R. Wauchope, C. Johnson, P. Krishnamoorthy, G. Andrei, R. Snoeck, J. Balzarini, K.L. Seley-Radtke, Bioorg. Med. Chem. 20, 3009 (2012)CrossRefGoogle Scholar
  18. 18.
    M. Viktoras, P. Grazina, T. Sigitas, Synthesis 2012, 1329 (2012)Google Scholar
  19. 19.
    L.J. Gao, H.L. Ji, L.C. Rong, D. Tang, Y.Y. Zha, Y.H. Shi, S.J. Tu, J. Heterocycl. Chem. 48, 957 (2011)CrossRefGoogle Scholar
  20. 20.
    Y.S. Dai, M.X. Cao, M.J. Zhuang, S. Xia, S.J. Tu, L.C. Rong, Synth. Commun. 41, 3039 (2011)CrossRefGoogle Scholar
  21. 21.
    L.C. Rong, X.Y. Li, H.Y. Wang, D.Q. Shi, S.J. Tu, Chem. Lett. 35, 1314 (2006)CrossRefGoogle Scholar
  22. 22.
    S.M. Tao, S. Xia, L.C. Rong, C.S. Cao, S.J. Tu, Res. Chem. Intermed. (2012). doi: 10.1007/s11164-012-0526-9

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Liangce Rong
    • 1
    • 2
  • Xianyong Wei
    • 1
  • Shimin Tao
    • 2
  • Yao Lu
    • 1
  • Ruilun Xie
    • 1
  • Jun Zhou
    • 1
  • Zhimin Zong
    • 1
  1. 1.School of Chemical Engineering and TechnologyChina University of Mining and TechnologyXuzhouPeople’s Republic of China
  2. 2.College of Chemistry and Chemical EngineeringJiangsu Normal UniversityXuzhouPeople’s Republic of China

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