Ionic liquid mediated one pot synthesis of substituted 2,4,6- triarylpyridines

International Journal of ChemTech Research

Volumn 2, Issue 1, 2010, Pages 289-294

  Ingole, Pravin G ^a   Jadhav, Sumit V ^a   Bajaj, Hari C ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Ethyl ammonium nitrate; Green chemistry; Ionic liquid; Triarylpyridine

Indexed keywords

2,4,6 TRIARYLPYRIDINE DERIVATIVE; 4 HYDROXYACETOPHENONE; ACETOPHENONE; ALDEHYDE; AMMONIUM ACETATE; ETHYL AMMONIUM NITRATE; IONIC LIQUID; NITRIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; VOLATILE ORGANIC COMPOUND;

ALDOL REACTION; ARTICLE; COST; MICHAEL ADDITION; ONE POT SYNTHESIS; RING CLOSING METATHESIS; SUBSTITUTION REACTION;

EID: 77953445880     PISSN: None     EISSN: 09744290     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Thompson C., The synthesis of 2,2′:6′,2″-terpyridine ligands - versatile building blocks for supramolecular chemistry, Coord. Chem. Rev., 1997, 160, 1-52.
2. Kim B.Y., Ahn J.B., Lee H.W., Kang S.K., Lee J.H., Shin J.S., Ahn S.K., Hong C.I. and Yoon S.S., Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione, Eur. J. Med. Chem., 2004, 3, 433-447.
3. Adib M., Tahermansouri H., Koloogani S.A., Mohammadi B. and Bijanzadeh H.R., Krohnke pyridines: an efficient solvent-free synthesis of 2,4,6-triarylpyridines, Tetrahedron Lett., 2006, 47, 5957-5960.
4. Kappe C.O., Biologically active dihydro pyrimidones of the Biginelli-type - a literature survey, Eur. J. Med. Chem., 2000, 35, 1043-1052.
5. Chen C., Tagami K. and Kishi Y., Ni(II)/Cr(II)-mediated coupling reaction: an asymmetric process, J. Org. Chem., 1995, 60, 5386-5387.
6. Heathcock C.H., Norman M.H. and Uchling D.E., Acyclic stereoselection. 29. Stereoselection in the Michael addition reaction. 1. The Mukaiyama-Michael reaction, J. Am. Chem. Soc., 1985, 107, 2797-2799.
7. Mukaiyama T., Kobayashi S. and Murakami M., An efficient method for the preparation of threo cross-aldols from silyl enol ethers and aldehydes using trityl perchlorate as a catalyst, Chem. Lett., 1985, 14, 447-450.
8. Chubb F., Hay A.S. and Sandin R.B., The Leuckart Reaction of Some 1,5-Diketones, J. Am. Chem. Soc., 1953, 75, 6042-6044.
9. Frank R.L. and Seven R.P., Pyridines. IV. A Study of the Chichibabin Synthesis, J. Am. Chem. Soc., 1949, 71, 2629-2635.
10. Lombard R. and Stephen J.P., Bull. Soc. Chim. Fr., 1958, 1458.
11. Krohnke F. and Zecher W., Syntheses Using the Michael Addition of Phridinium Salts, Angew. Chem. Int. Ed., 1962, 1, 626-632.
12. Potts K.T., Cipullo M.J., Ralli P. and Theodoridis G., Ketene dithio acetals as synthetic intermediates. Synthesis of unsaturated 1,5- diketones, J. Am. Chem. Soc., 1981, 103, 3584-3585.
13. Kobayashi T., Kakiuchi H. and Kato H., On the Reaction of N-(Diphenylphosphinyl)-1-phenylethanimine with Aromatic Aldehydes Giving 4-Aryl-2,6-diphenylpyridine Derivatives, Bull. Chem. Soc. Jpn., 1991, 64, 392-395.
14. Palacios F., Retana A.M.O. and Oyarzabal J., A "one pot" synthesis of polysubstituted pyridines from metallated alkylphosphonates, nitriles and α,β-unsaturated ketones, Tetrahedron Lett., 1996, 37, 4577-4580.
15. Anastas P.T. and Warner J.C., Green Chemistry, Theory and Practice. Oxford University Press, 1998.
16. Huang X.Q., Li H.X., Wang J.X. and Jia X.F., A Rapid and Efficient Synthesis of 2, 4, 6-Triarylpyridines under Microwave Irradiation, Chinese Chemical Lett., 2005, 16, 607-608.
17. Heravia M.M., Bakhtiaria K., Darooghehaa Z. and Bamoharram F.F., An efficient synthesis of 2,4,6-triarylpyridines catalyzed by heteropolyacid under solvent-free conditions, Catalysis Comm., 2007, 8, 1991-1994.
18. Wu H., Lu L., Shen Y., Wan Y. and Yu K., Sequential Aldol/Michael Addition Reaction in Ionic Liquid Catalyzed by Morpholine: A Convenient Synthesis of 1,3,5-Triaryl-1,5-pentanedione, Synthetic Comm., 2006, 36, 1193-1200.
19. Smith N.M., Raston C.L., Smith C.B. and Sobolev A.N., PEG mediated synthesis of amino-functionalised 2,4,6-triarylpyridines, Green Chem., 2007, 9, 1185-1190.
20. Rajagopal R. and Srinivasan K.V., Ultrasound promoted para-selective nitration of phenols in ionic liquid, Ultrasonics sonochemistry, 2003, 10, 41-43.