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Iron(III) phosphate as a green and reusable catalyst for the synthesis of 4,6-disubstituted 2-aminopyridine-3-carbonitriles

Abstract

Condensation reaction of aryl aldehydes, methyl ketones, malononitrile, and ammonium acetate in the presence of the green and recyclable catalyst FePO4 affords the corresponding 4,6-disubstituted 2-aminopyridine-3-carbonitriles. Some new derivatives of these compounds are synthesized. The catalyst can be also recycled and reused several times.

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References

  1. Orru RVA, Ruijter E (2010) Synthesis of Heterocycles via Multicomponent Reactions II. Topics in Heterocyclic Chemistry, vol 25. Springer, Berlin, Heidelberg

    Google Scholar 

  2. Behbahani FK, Yektanezhad T, Khorrami AR (2010) Heterocycles 81:2313

    Article  CAS  Google Scholar 

  3. Behbahani FK, Ziaei P (2012) Chem Heterocycl Compd 48:1011

    Article  CAS  Google Scholar 

  4. Behbahani FK, Ziaei P (2012) Chin J Chem 30:65

    Article  CAS  Google Scholar 

  5. Behbahani FK, Homafar M (2011) Syn React Inorg Met 42:291

    Article  Google Scholar 

  6. Kanjariya HM, Radhakrishnan TV, Ramchandran KR, Hansa P (2004) Indian J Chem Sect B 43:1569

    Google Scholar 

  7. Popat KH, Kachhadia VV, Nimavat KS, Joshi HS (2004) J Indian Chem Soc 81:157

    CAS  Google Scholar 

  8. Stoltefuss J, Goldmann S, Straub A, Boeshagen H, Bechem M, Gross R, Hebisch S, Huetter J, Rounding HP (1995) Preparation of aryl(alkoxycarbonyldihydropyridyl)quinolines as cardiotonics. US Patent 5432282, 11 Jul 1995

  9. Murata T, Shimada M, Kadono H, Sakakibara S, Yoshino T, Masuda T, Shimazaki M, Shintani T, Fuchikami K, Bacon KB, Lowinger TBZ (2004) Bioorg Med Chem Lett 14:4013

    Article  CAS  Google Scholar 

  10. Shi F, Tu V, Fang F, Li T (2005) Arkivoc i:137

    Google Scholar 

  11. Tu SJ, Jiang H, Zhuang QY, Miao CB, Shi DQ, Wang XS, Gao YC (2003) Chin J Org Chem 23:488

    CAS  Google Scholar 

  12. Zhou WJ, Ji SJ, Shen ZL (2006) J Organomet Chem 691:1356

    Article  CAS  Google Scholar 

  13. Jin TS, Wang AQ, Shi F, Han LS, Liu LB, Li TS (2006) Arkivoc xiv:78

    Google Scholar 

  14. Shestopalov AM, Naumov OA (2003) Russ Chem Bull 52:1380

    Article  CAS  Google Scholar 

  15. Vasiliev AN, Kayukov YS, Nasakin OE, Lyshchikov AN, Nesterov VN, Kayukova OV, Poulkherovskaya OV (2001) Chem Heterocycl Compd 37:309

    Article  CAS  Google Scholar 

  16. Sheik Mansoor S, Aswin K, Logaiya K, Sudhan SPN (2012) J Saudi Chem Soc. doi:10.1016/j.jscs.2012.07.011

  17. Banothu J, Bavantula R, Crooks PA (2013) Iran J Catal 3:41

    CAS  Google Scholar 

  18. Sarda SR, Kale JD, Wasmatkar SK, Kadam VS, Ingole PG, Jadhav WN, Pawar RP (2009) Mol Divers 13:545

    Article  CAS  Google Scholar 

  19. Osman H, Arshad A, Lam CK, Bagley MC (2012) Chem Cent J 6:32

    Article  CAS  Google Scholar 

Download references

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Correspondence to Farahnaz K. Behbahani.

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Zadpour, M., Behbahani, F.K. Iron(III) phosphate as a green and reusable catalyst for the synthesis of 4,6-disubstituted 2-aminopyridine-3-carbonitriles. Monatsh Chem 146, 1865–1869 (2015). https://doi.org/10.1007/s00706-015-1456-1

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  • DOI: https://doi.org/10.1007/s00706-015-1456-1

Keywords

  • Condensation reaction
  • FePO4
  • Disubstituted pyridine
  • Arylnicotinonitrile