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Three-component synthesis of some 2-amino-5-hydroxy-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles and 2-(cyanoamino)-4-hydroxypyrimidine-5-carbonitriles

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Abstract

Nine new 2-amino-5-hydroxy-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles and eight 2-(cyanoamino)-4-hydroxypyrimidine-5-carbonitriles have been synthesized in a simple and convenient method by three-component condensation of aromatic aldehydes, ethyl cyanoacetate, and 3,5-diamino-1,2,4-triazole or cyanoguanidine hydrochloride in alkaline ethanol. All new synthesized compounds were characterized by nuclear magnetic resonance (NMR), infrared (IR), ultraviolet (UV), mass spectrometry (MS), and elemental analyses.

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References

  1. Vu CB, Shields P, Peng B, Kumaravel G, Jin XW, Phadke D, Wang J, Engber T, Ayyub E, Petter RC (2004) Bioorg Med Chem Lett 14:4835

    Article  CAS  Google Scholar 

  2. Jackson R, Ghosh D, Paterson G (2000) Pest Manage Sci 56:1065

    Article  CAS  Google Scholar 

  3. Deng JZ, McMasters DR, Rabbat PMA, Williams PD, Coburn CA, Yan Y, Kuo LC, Lewis SD, Lucas BJ, Krueger JA, Strulovici B, Vacca JP, Lylea TA, Burgey CS (2005) Bioorg Med Chem Lett 15:4411

    Article  CAS  Google Scholar 

  4. Rusinov VL, Petrov AY, Pilicheva TL (1986) Khim Farm Zh 20:178

    CAS  Google Scholar 

  5. Rusinov VL, Myasnikov AV, Pilicheva TL (1990) Khim Farm Zh 24:39

    CAS  Google Scholar 

  6. Okamura T, Kurogi Y, Hashimoto K, Nishikawa K, Nagao Y (2004) Bioorg Med Chem Lett 14:2443

    Article  CAS  Google Scholar 

  7. Novinson T, Springer RH, O’Brien DE, Scholten MB, Miller JP, Robins RK (1982) J Med Chem 25:420

    Article  CAS  Google Scholar 

  8. Kleschick WA, Costales MJ, Dunbar JE, Meikle RW, Monte WT, Pearson NR, Snider SW, Vinogradoff AP (1990) Pestic Sci 29:341

    Article  CAS  Google Scholar 

  9. Chen Q, Zhu X-L, Jiang L-L, Liu Z-M, Yang G-F (2008) Eur J Med Chem 43:595

    Article  CAS  Google Scholar 

  10. Amr AE, Hegab MI, Ibrahim AA, Abdalah MM (2003) Monatsh Chem 134:1395

    CAS  Google Scholar 

  11. Amr AE, Abdulla MM (2002) Indian J Heterocycl Chem 12:129

    CAS  Google Scholar 

  12. Nehad AA, Amr AE, Alhusien AI (2007) Monatsh Chem 138:559

    Article  Google Scholar 

  13. Shaban MAE, Morgaan AEA (1999) Adv Heterocycl Chem 75:243

    Article  CAS  Google Scholar 

  14. Rashad AE, Heikal OA, El-Nezhawy AOH, Abdel-Megeid FME (2005) Heteroat Chem 16:226

    Article  CAS  Google Scholar 

  15. Wang Y, Sarris K, Sauer DR, Djuric SW (2007) Tetrahedron Lett 48:2237

    Article  CAS  Google Scholar 

  16. Chen H, Shang Z, Chang J (2006) Synth Commun 36:445

    Article  CAS  Google Scholar 

  17. Guetzoyan LJ, Spooner RA, Lord JM, Roberts LM, Clarkson GJ (2010) Eur J Med Chem 45:275

    Article  CAS  Google Scholar 

  18. Nagamatsu T, Yamasaki H, Akiyama T, Hara S, Mori K, Kusakabe H (1999) Synthesis 4:655

    Article  Google Scholar 

  19. Khattab AF, El-Essawy FA (2005) J Chem Res 11:736

    Article  Google Scholar 

  20. Kumar R, Nair RR, Dhiman SS, Sharma J, Prakash O (2009) Eur J Med Chem 44:2260

    Article  CAS  Google Scholar 

  21. Desenko SM, Kolos NN, Tueni M, Orlov VD (1990) Khim Geterotsikl Soedin 7:938

    Google Scholar 

  22. Desenko SM, Orlov VD, Lipson VV (1990) Khim Geterotsikl Soedin 1638

  23. Deshmukh MB, Salunkhe SM, Patil DR, Anbhule PV (2009) Eur J Med Chem 44:265

    Article  Google Scholar 

  24. Shaaban MR (2008) J Fluorine Chem 129:1156

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Support of this investigation by Vali-E-Asr University is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Vali-e-Asr University, 77176, Rafsanjan, Islamic Republic of Iran

    Reza Ranjbar-Karimi, Khalil Beiki-Shoraki & Asghar Amiri

Authors
  1. Reza Ranjbar-Karimi
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  2. Khalil Beiki-Shoraki
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  3. Asghar Amiri
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Correspondence to Reza Ranjbar-Karimi.

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Ranjbar-Karimi, R., Beiki-Shoraki, K. & Amiri, A. Three-component synthesis of some 2-amino-5-hydroxy-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles and 2-(cyanoamino)-4-hydroxypyrimidine-5-carbonitriles. Monatsh Chem 141, 1101–1106 (2010). https://doi.org/10.1007/s00706-010-0371-8

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  • DOI: https://doi.org/10.1007/s00706-010-0371-8

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