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

Molecular Diversity

Volumn 13, Issue 4, 2009, Pages 545-549

  Sarda, Swapnil R ^a   Kale, Jagpal D ^a   Wasmatkar, Sunil K ^b   Kadam, Vijay S ^b   Ingole, Pravin G ^b   Jadhav, Wamanrao N ^b   Pawar, Rajendra P ^b,c  

^a JES College   (India)

^b DNYANOPASAK COLLEGE   (India)

^c DEOGIRI COLLEGE   (India)

Author keywords

2 amino 3 cyanopyridine; 2 amino 4,6 diphenylpyridine 3 carbonitrile; Chalcone; Ionic liquid; Malononitrile

Indexed keywords

2 AMINO 4 (4 CHLOROPHENYL) 6 (4 METHOXYPHENYL) PYRIDINE 3 CARBONITRILE; 2 AMINO 4 (4 METHOXYPHENYL) 6 PHENYLPYRIDINE 3 CARBONITRILE; 2 AMINO 4,6 DIPHENYLPYRIDINE 3 CARBONITRILE; AMMONIUM NITRATE; CYANIDE; IONIC LIQUID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; QUANTUM YIELD; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

CATALYSIS; IONIC LIQUIDS; NITRILES; PYRIDINES; QUATERNARY AMMONIUM COMPOUNDS; SOLVENTS;

EID: 70349916233     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9132-1     Document Type: Article

References (22)

1. ZN Siddiqui M Asad, et al. 2008 Synthesis and biological activity of heterocycles from chalcone Med Chem Res 17 318 325 10.1007/s00044-007-9067-y 10.1007/s00044-007-9067-y 1:CAS:528:DC%2BD1cXovF2gtb8%3D
2. HM Kanjariya TV Radhakrishnan KR Ramchandran P Hansa 2004 Studies on biological evaluation of cyanopyrans and pyrazolines using microwave assisted synthesis Indian J Chem Sect B 43 1569 1573
3. KH Popat VV Kachhadia KS Nimavat HS Joshi 2004 Synthesis of some new cyanopyrans and cyanopyridines and their biological activites J Indian Chem Soc 81 157 159 1:CAS:528:DC%2BD2cXjs1ylsrY%3D
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. T Murata M Shimada H Kadono S Sakakibara T Yoshino T Masuda M Shimazaki T Shintani K Fuchikami KB Bacon KB Ziegelbauer TB Lowinger 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 10.1016/j.bmcl.2004.05.040 15225717 10.1016/j.bmcl.2004.05.040 1:CAS:528:DC%2BD2cXlt1egsrw%3D (Pubitemid 38844415)
6. Landguist JK (1984) Comprehensive heterocyclic chemistry. Pergamon, Oxford, UK, p 155
7. F Shi S Tu F Fang T Li 2005 One-pot synthesis of 2-amino-3-cyanopyridine derivatives under microwave irradiation without solvent Arkivoc i 137 142 (Pubitemid 40390029)
8. SJ Tu H Jiang QY Zhuang CB Miao DQ Shi XS Wang YC Gao 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 1:CAS:528:DC%2BD3sXksVymur8%3D
9. WJ Zhou SJ Ji ZL Shen 2006 An efficient synthesis of ferrocenyl substituted 3-cyanopyridine derivatives under ultrasound irradiation J Organomet Chem 691 1356 1360 10.1016/j.jorganchem.2005.09.046 10.1016/j.jorganchem.2005. 09.046 1:CAS:528:DC%2BD28XitVOhsL4%3D (Pubitemid 43312865)
10. TS Jin AQ Wang F Shi LS Han LB Liu TS Li 2006 Hexadecyl-dimethyl benzyl ammonium bromide: an efficient catalyst for a clean one-pot synthesis of tetrahydrobenzopyran derivatives in water Arkivoc xiv 78 86
11. EV Tret'yakova OB Flekhter FZ Galin LV Spirikhin GA Tolstikov 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 10.1023/B:RUJO.0000019737.78635.bd 10.1023/B:RUJO.0000019737.78635.bd (Pubitemid 39012407)
12. AM Shestopalov OA Naumov 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 10.1023/A:1024835412937 10.1023/A:1024835412937 1:CAS:528:DC%2BD3sXlslSiu7c%3D
13. AN Vasiliev YS Kayukov OE Nasakin AN Lyshchikov VN Nesterov OV Kayukova OV Poulkherovskaya 2001 Synthesis of alkyl 5,6-dialkyl-2-amino-3-cyanopyridine- 4-carboxylates Chem Heterocycl Compd 37 309 314 10.1023/A:1017503015471 10.1023/A:1017503015471 1:CAS:528:DC%2BD3MXmtleqt7c%3D
14. T Welton 1999 Room-temperature ionic liquids. Solvents for synthesis and catalysis Chem Rev 99 2071 2084 10.1021/cr980032t 11849019 10.1021/cr980032t 1:CAS:528:DyaK1MXkt1artrw%3D
15. SP Panchgalle UR Kalkote PS Niphadkar PN Joshi SP Chavan G Chaphekar 2004 Sn-β molecular sieve catalysed Baeyer-Villiger oxidation in ionic liquid at room temperature Green Chem 6 308 309 10.1039/b406077f 10.1039/b406077f 1:CAS:528:DC%2BD2cXmtVWgt7o%3D (Pubitemid 39163784)
16. NE Leadbeater HM Torenius H Tye 2003 Microwave-assisted mannich-type three-component reactions Mol Divers 7 135 144 10.1023/B:MODI.0000006822.51884. e6 14870842 10.1023/B:MODI.0000006822.51884.e6 1:CAS:528:DC%2BD3sXpsFOgurw%3D (Pubitemid 38095148)
17. R Lavilla I Carranco JL Díaz MC Bernabeu G de la Rosa 2003 Dihydropyridines in MCRs. Tandem processes leading to modular tetrahydroquinoline systems with up to diversity elements Mol Divers 6 171 175 15068078 10.1023/B:MODI.0000006756.83821.80 1:CAS:528:DC%2BD3sXpsFOgt74%3D (Pubitemid 38089853)
18. BR Madje SS Shindalkar MS Shingare 2004 One-pot Biginelli condensation reaction in an ionic liquid Indian J Heterocycl Chem 14 87 89 1:CAS:528:DC%2BD2cXovVelt7s%3D
19. Y Hu J Chen Z Le Q Zheng 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 10.1081/SCC-200050380 10.1081/SCC-200050380 1:CAS:528:DC%2BD2MXivFGjt7o%3D (Pubitemid 40389515)
20. R Rajagopal KV Srinivasan 2003 Ultrasound promoted para-selective nitration of phenols in ionic liquid Ultrason Sonochem 10 41 43 10.1016/S1350-4177(02)00099-8 12457950 10.1016/S1350-4177(02)00099-8 1:CAS:528:DC%2BD38XovFCjsbs%3D (Pubitemid 35375914)
21. SR Sarda MY Pathan VV Paike PR Pachmase WN Jadhav RP Pawar 2006 A facile synthesis of flavones using recyclable ionic liquid under microwave irradiation Arkivoc xvi 43 48
22. RS Bhosale PA Suryawanshi SA Ingle MN Lokhande SP More SB Mane SV Bhosale RP Pawar 2006 Ionic liquid promoted synthesis of β-enamino ketones at room temperature Synlett 6 933 935