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.
References
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
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
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
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
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
Landguist JK (1984) Comprehensive heterocyclic chemistry. Pergamon, Oxford, UK, p 155
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
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
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
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
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
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
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
Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99: 2071–2084. doi:10.1021/cr980032t
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
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
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
Madje BR, Shindalkar SS, Shingare MS (2004) One-pot Biginelli condensation reaction in an ionic liquid. Indian J Heterocycl Chem 14: 87–89
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
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
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
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
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-009-9132-1