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An efficient protocol for the synthesis of 2-amino-4,6-diphenylpyridine-3-carbonitrile using ionic liquid ethylammonium nitrate

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Abstract

Chalcones on condensation with malononitrile and ammonium acetate in the presence of ionic liquid ethylammonium nitrate affords the corresponding 2-amino-4, 6-diphenylpyridine-3-carbonitrile in excellent yield. The ionic liquid is recycled and reused several times.

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References

  1. Siddiqui ZN, Asad M et al (2008) Synthesis and biological activity of heterocycles from chalcone. Med Chem Res 17: 318–325. doi:10.1007/s00044-007-9067-y

    Article  CAS  Google Scholar 

  2. Kanjariya HM, Radhakrishnan TV, Ramchandran KR, Hansa P (2004) Studies on biological evaluation of cyanopyrans and pyrazolines using microwave assisted synthesis. Indian J Chem Sect B 43: 1569–1573

    Google Scholar 

  3. Popat KH, Kachhadia VV, Nimavat KS, Joshi HS (2004) Synthesis of some new cyanopyrans and cyanopyridines and their biological activites. J Indian Chem Soc 81: 157–159

    CAS  Google Scholar 

  4. Jurgen S, Siegfried G, Alexander S, Horst B, Martin B, Rainer G, Siegbert H, Joachim H, Howard-Paul R (1995) Process for preparing 1,4-dihydro-2-amino-3-carboxy-5-cyano-pyridine derivatives. US Patent 5432282

  5. Murata T, Shimada M, Kadono H, Sakakibara S, Yoshino T, Masuda T, Shimazaki M, Shintani T, Fuchikami K, Bacon KB, Ziegelbauer KB, Lowinger TB (2004) Synthesis and structure-activity relationships of novel IKK-β inhibitors. Part 2: improvement of in vitro activity. Bioorg Med Chem Lett 14: 4013–4017. doi:10.1016/j.bmcl.2004.05.040

    Article  PubMed  CAS  Google Scholar 

  6. Landguist JK (1984) Comprehensive heterocyclic chemistry. Pergamon, Oxford, UK, p 155

    Google Scholar 

  7. Shi F, Tu S, Fang F, Li T (2005) One-pot synthesis of 2-amino-3-cyanopyridine derivatives under microwave irradiation without solvent. Arkivoc i: 137–142

    Google Scholar 

  8. Tu SJ, Jiang H, Zhuang QY, Miao CB, Shi DQ, Wang XS, Gao YC (2003) One-pot synthesis of 2-amino-3-cyano-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]-pyran under ultrasonic irradiation without catalyst. Chin J Org Chem 23: 488–490

    CAS  Google Scholar 

  9. Zhou WJ, Ji SJ, Shen ZL (2006) An efficient synthesis of ferrocenyl substituted 3-cyanopyridine derivatives under ultrasound irradiation. J Organomet Chem 691: 1356–1360. doi:10.1016/j.jorganchem.2005.09.046

    Article  CAS  Google Scholar 

  10. Jin TS, Wang AQ, Shi F, Han LS, Liu LB, Li TS (2006) Hexadecyl-dimethyl benzyl ammonium bromide: an efficient catalyst for a clean one-pot synthesis of tetrahydrobenzopyran derivatives in water. Arkivoc xiv: 78–86

    Google Scholar 

  11. Tret’yakova EV, Flekhter OB, Galin FZ, Spirikhin LV, Tolstikov GA (2003) Synthesis of 2-amino-4-aryl-3-cyano-4H-pyrano and 2-amino-3-cyanothieno derivatives of cyclopentanonopimaric acid. Russ J Org Chem 39(12): 1738–1740. doi:10.1023/B:RUJO.0000019737.78635.bd

    Article  Google Scholar 

  12. Shestopalov AM, Naumov OA (2003) Synthesis of substituted 2-amino-3-cyano-7,9-dimethyl-4H- pyrano[2′′, 3′′: 4,5]-thieno-[2,3-b]pyridines. Russ Chem Bull 52(6): 1380–1385. doi:10.1023/A:1024835412937

    Article  CAS  Google Scholar 

  13. Vasiliev AN, Kayukov YS, Nasakin OE, Lyshchikov AN, Nesterov VN, Kayukova OV, Poulkherovskaya OV (2001) Synthesis of alkyl 5,6-dialkyl-2-amino-3-cyanopyridine-4-carboxylates. Chem Heterocycl Compd 37: 309–314. doi:10.1023/A:1017503015471

    Article  CAS  Google Scholar 

  14. Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99: 2071–2084. doi:10.1021/cr980032t

    Article  PubMed  CAS  Google Scholar 

  15. Panchgalle SP, Kalkote UR, Niphadkar PS, Joshi PN, Chavan SP, Chaphekar G (2004) Sn-β molecular sieve catalysed Baeyer–Villiger oxidation in ionic liquid at room temperature. Green Chem 6: 308–309. doi:10.1039/b406077f

    Article  CAS  Google Scholar 

  16. Leadbeater NE, Torenius HM, Tye H (2003) Microwave-assisted mannich-type three-component reactions. Mol Divers 7: 135–144. doi:10.1023/B:MODI.0000006822.51884.e6

    Article  PubMed  CAS  Google Scholar 

  17. Lavilla R, Carranco I, Díaz JL, Bernabeu MC, de la Rosa G (2003) Dihydropyridines in MCRs. Tandem processes leading to modular tetrahydroquinoline systems with up to diversity elements. Mol Divers 6: 171–175

    Article  PubMed  CAS  Google Scholar 

  18. Madje BR, Shindalkar SS, Shingare MS (2004) One-pot Biginelli condensation reaction in an ionic liquid. Indian J Heterocycl Chem 14: 87–89

    CAS  Google Scholar 

  19. Hu Y, Chen J, Le Z, Zheng Q (2005) Organic reactions in ionic liquids: ionic liquids ethylammonium nitrate promoted knoevenagel condensation of aromatic aldehydes with active methylene compounds. Synth Commun 35: 739–744. doi:10.1081/SCC-200050380

    Article  CAS  Google Scholar 

  20. Rajagopal R, Srinivasan KV (2003) Ultrasound promoted para-selective nitration of phenols in ionic liquid. Ultrason Sonochem 10: 41–43. doi:10.1016/S1350-4177(02)00099-8

    Article  PubMed  CAS  Google Scholar 

  21. Sarda SR, Pathan MY, Paike VV, Pachmase PR, Jadhav WN, Pawar RP (2006) A facile synthesis of flavones using recyclable ionic liquid under microwave irradiation. Arkivoc xvi: 43–48

    Google Scholar 

  22. Bhosale RS, Suryawanshi PA, Ingle SA, Lokhande MN, More SP, Mane SB, Bhosale SV, Pawar RP (2006) Ionic liquid promoted synthesis of β-enamino ketones at room temperature. Synlett 6: 933–935

    Google Scholar 

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Correspondence to Rajendra P. Pawar.

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Sarda, S.R., Kale, J.D., Wasmatkar, S.K. et al. An efficient protocol for the synthesis of 2-amino-4,6-diphenylpyridine-3-carbonitrile using ionic liquid ethylammonium nitrate. Mol Divers 13, 545–549 (2009). https://doi.org/10.1007/s11030-009-9132-1

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  • DOI: https://doi.org/10.1007/s11030-009-9132-1

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