Synlett 2016; 27(11): 1689-1692
DOI: 10.1055/s-0035-1561381
letter
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Polyfunctionalized Pyrimidine Derivatives

Mohammad Mahdavi
a   Drug Design and Development Research Center, Tehran University of Medical Sciences, Theran, Iran
,
Hossein Kianfard
b   School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
,
Mina Saeedi
c   Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
d   Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
,
Parviz Rashidi Ranjbar
b   School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
,
Abbas Shafiee*
e   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 16 October 2015

Accepted after revision: 20 January 2016

Publication Date:
17 March 2016 (online)


Abstract

A simple and direct procedure was developed for the synthesis of a novel series of polyfunctionalized pyrimidines. They were prepared via reaction of N-(substituted carbamothioyl)benzimidamides (prepared from the reaction of benzimidamide hydrochloride and isothiocyanates) and malononitrile in the presence of CuBr/Et3N in DMF at 80 °C.

Supporting Information

 
  • References

  • 1 Gore RP, Rajput AP. Drug Invent. Today 2013; 5: 148
  • 2 Price D, May EL, Pickel FD. J. Am. Chem. Soc. 1940; 62: 2818
  • 3 Selvam TP, James CR, Dniandev PV, Valzita SK. Res. Pharm. 2012; 2: 1
  • 4 Wyatt GR. Biochem. J. 1951; 48: 584
    • 5a Gülcan M, Sönmez M, Berber I. Turk. J. Chem. 2012; 36: 189
    • 5b Sönmez M, Çelebi M, Levent A, Berber İ, Şentürk Z. J. Coord. Chem. 2010; 63: 848
  • 6 Brown DJ, Evans RF, Cowden WB, Fenn MD. The Pyrimidines. John Wiley and Sons; New York: 1994: 149-239
  • 7 Zhuang Q, Han H, Wang S, Tu S, Rong L. Synth. Commun. 2009; 39: 516
    • 8a Xia S, Yin S, Tao S, Shi Y, Rong L, Wei X, Zong Z. Res. Chem. Intermed. 2012; 38: 2435
    • 8b Ryabukhin SV, Plaskon AS, Boron SY, Volochnyuk DM, Tolmachev AA. Mol. Diversity 2011; 15: 189
  • 9 Ahmad OK, Hill MD, Movassaghi M. J. Org. Chem. 2009; 74: 8460
  • 10 Karpov AS, Müller TJ. J. Synthesis 2003; 2815
  • 11 Estrada AA, Lyssikatos JP, St-Jean F, Bergeron P. Synlett 2011; 2387
  • 12 Mukerjee AK, Ashare R. Chem. Rev. 1991; 91: 1
  • 13 Douglass IB, Dains FB. J. Am. Chem. Soc. 1934; 56: 719
  • 14 Gama Y, Shibuya I, Shimizu M. Synth. Commun. 1999; 29: 1493
  • 15 Kim KS, Qian L. Tetrahedron Lett. 1993; 34: 7677
  • 16 Levallet C, Lerpiniere J, Ko YS. Tetrahedron 1997; 53: 5291
  • 17 Yella R, Khatun N, Rout SK, Patel BK. Org. Biomol. Chem. 2011; 9: 3235
  • 18 Ghosh H, Yella R, Nath J, Patel BK. Eur. J. Org. Chem. 2008; 6189
  • 19 Ghosh H, Yella R, Ali AR, Sahoo SK, Patel BK. Tetrahedron Lett. 2009; 50: 2407
  • 20 Nath J, Patel BK. Jamir L, Sinha UB, Satyanarayana KV. V. V. Green Chem. 2009; 11: 1503
  • 21 Ali AR, Ghosh H, Patel BK. Tetrahedron Lett. 2010; 51: 1019
  • 22 Singh CB, Ghosh H, Murru S, Patel BK. J. Org. Chem. 2008; 73: 2924
  • 23 Nath J, Ghosh H, Yella R, Patel BK. Eur. J. Org. Chem. 2009; 1849
  • 24 Omar A.-MM. E, Habib NS, Aboulwafa OM. Synthesis 1977; 864
  • 25 Wang X, Zhang L, Zu Y, Krishnamurthy D, Senanayake CH. Tetrahedron Lett. 2004; 45: 7167
  • 26 Murru S, Mondal P, Yella R, Patel BK. Eur. J. Org. Chem. 2009; 5406
    • 27a Saeedi M, Mahdavi M, Foroumadi A, Shafiee A. Tetrahedron 2013; 69: 3506
    • 27b Mahdavi M, Asadi M, Saeedi M, Ebrahimi M, Rasouli MA, Ranjbar PR, Foroumadi A, Shafiee A. Synthesis 2012; 44: 3649
    • 27c Rasouli MA, Mahdavi M, Ranjbar PR, Saeedi M, Shafiee A, Foroumadi A. Tetrahedron Lett. 2012; 53: 7088
    • 27d Mahdavi M, Foroughi N, Saeedi M, Karimi M, Alinezhad H, Foroumadi A, Shafiee A, Akbarzadeh T. Synlett 2014; 25: 385
    • 27e Nahavandian S, Allameh S, Saeedi M, Ansari S, Mahdavi M, Foroumadi A, Shafiee A. Helv. Chim. Acta 2015; 98: 1028
    • 27f Alizadeh BH, Saeedi M, Dehghan G, Foroumadi A, Shafiee A. J. Iran Chem. Soc. 2015; 12: 605
    • 27g Mohammadi-Khanaposhtani M, Saeedi M, Zafarghandi NS, Mahdavi M, Sabourian R, Razkenari EK, Alinezhad H, Khanavi M, Shafiee A, Foroumadi A, Akbarzadeh T. Eur. J. Med. Chem. 2015; 92: 79
    • 28a Masquelin T, Obrecht D. Tetrahedron 2001; 57: 153
    • 28b Kim H.-Y, Kwak SH, Lee G.-H, Gong Y.-D. Tetrahedron 2014; 70: 87373