Highly Efficient, One Pot Synthesis and Oxidation of Hantsch 1,4-Dihydropyridines Mediated by Iodobenzene Diacetate (III) Using Conventional Heating, Ultrasonic and Microwave Irradiation

Khalid Hussain, Deepak Wadhwa

Department of chemistry, Kurukshetra University, Kurukshetra, India.
Mewat Engineering College (WAKF), Nuh, India.

DOI: 10.4236/ijoc.2014.43019                

Abstract

A mild, general, convenient, and efficient one-pot synthesis of 4-arylpyridines (4) is described using conventional heating, ultrasound and microwave irradiation. Aryl aldehydes (2) were efficiently condensed with ethylacetoacetate (1) and ammonium acetate in acetonitrile to give dihydropyridine intermediates (4). The latter underwent a smooth Iodobenzene Diacetate (III) mediated aromatization reaction in the same pot to afford 4-arylpyridines (4) in good to excellent yields.

Keywords

Dihydropyridines, Iodobenzene Diacetate, Ultrasonic, Microwave, One-Pot, Formylpyrazoles

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Tietze, L.F. (1996) Domino Reactions in Organic Synthesis. Chemical Reviews, 96, 115-136. http://dx.doi.org/10.1021/cr950027e
[2]	Mason, T.J. and Meulenaer, E.C.D. (1998) Practical Considerations for Process Optimisation. Synthetic Organic Sono-chemistry. Plenum Press, New York and London.
[3]	Kappe, C.O. (2004) Controlled Microwave Heating in Modern Organic Synthesis. Angewandte Chemie International Edition, 43, 6250-6284. http://dx.doi.org/10.1002/anie.200400655
[4]	Tsuruo, T., Iida, H., Nojiri, M., Tsukagoshi, S. and Sakurai, Y. (1983) Circumvention of Vincristine and Adriamycin Resistance in Vitro and in Vivo by Calcium Influx Blockers. Cancer Research, 43, 2905-2910.
[5]	Chapman, R.W., Danko, G. and Siegels, M.I. (1984) Effect of Extra- and Intracellular Calcium Blockers on Histamine and Antigen-Induced Bronchospasms in Guinea Pigs and Rats. Pharmacology, 29, 282-291. http://dx.doi.org/10.1159/000138024
[6]	Malaise, W.J. and Mathias, P.C.F. (1985) Stimulation of Insulin Release by an Organic Calcium Agonist. Diabetologia, 28, 153-156.
[7]	Krauze, A., Germane, S., Eberlins, O., Sturms, I., Klusa, V. and Duburs, G. (1999) Derivatives of 3-Cyano-6-Phenyl- 4-(3’-Pyridyl)-Pyridine-2(1H)-Thione and Their Neurotropic Activity. European Journal of Medicinal Chemistry, 34, 301-310. http://dx.doi.org/10.1016/S0223-5234(99)80081-6
[8]	Peri, R., Padmanabhan, S., Singh, S., Rutledge, A. and Triggle, D.J. (2000) Permanently Charged Chiral 1,4-Dihydropyridines: Molecular Probes of L-Type Calcium Channels. Synthesis and Pharmacological Characterization of Methyl (ω-Trimethylalkylammonium) 1,4-Dihydro-2,6-Dimethyl-4-(3-Nitrophenyl)-3,5-Pyridinedicarboxylate Iodide. Calcium Channel Antagonists. Journal of Medicinal Chemistry, 43, 2906-2914. http://dx.doi.org/10.1021/jm000028l
[9]	Zhou, X., Zhang, L., Tseng, E., Scott-Ramsay, E., Schentag, J.J., Coburn, R.A. and Morris, M.E. (2005) New 4-Aryl- 1,4-Dihydropyridines and 4-Arylpyridines as p-Glycoprotein Inhibitors. Drug Metabolism and Disposition, 33, 321-328. http://dx.doi.org/10.1124/dmd.104.002089
[10]	Karade, N.N., Gampawar, S.V., Kondre, J.M. and Shinde, S.V. (2008) An Efficient Combination of Dess-Martin Periodinane with Molecular Iodine and KBr for the Facile Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines. Arkivoc, xii, 9-16. http://dx.doi.org/10.3998/ark.5550190.0009.c02
[11]	Cheng, D.P. and Chen, Z.C. (2002) Hypervalent Iodine in Synthesis. 76. An Efficient Oxidation of 1,4-Dihydropyridines to Pyridines Using Iodobenzene Diacetate. Synthetic Communications, 32, 793-798. http://dx.doi.org/10.1081/SCC-120002521
[12]	Kumar, P. (2009) Solid State Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines to Pyridines Using Iodobenzene Diacetate or Hydroxy(tosyloxy)iodobenzene. Chinese Journal of Chemistry, 27, 1487-1491. http://dx.doi.org/10.1002/cjoc.200990250
[13]	Kumar, P. (2010) A Novel, Facile, Simple and Convenient Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines to Pyridines Using Polymeric Iodosobenzene with KBr. Journal of Heterocyclic Chemistry, 47, 1429-1433.
[14]	Lee, K.H. and Ko, K.Y. (2002) Aromatization of Hantzsch 1,4-Dihydropyridines with [Hydroxy(tosyloxy)iodo] Benzene. Bulletin of the Korean Chemical Society, 23, 1505-1506.
[15]	Lee, J.W. and Ko, K.Y. (2004) Aromatization of Hantzsch 1,4-Dihydropyridines with a Polymer-Supported Hypervalent Iodine Reagent. Bulletin of the Korean Chemical Society, 25, 19-20.
[16]	Varma, R.S. and Kumar, D. (1999) Solid State Oxidation of 1,4-Dihydropyridines to Pyridines Using Phenyliodine(III)Bis(trifluoroacetate) or Elemental Sulfur. Journal of the Chemical Society, Perkin Transactions 1, 24, 1755-1757.
[17]	Varvoglis, A. (1997) Chemical Transformations Induced by Hypervalent Iodine Reagents. Tetrahedron, 53, 1179-1255. http://dx.doi.org/10.1016/S0040-4020(96)00970-2
[18]	Wirth, T., Chiai, M., Zhdankin, V.V., Koser, G.F., Tohma, H. and Kita, Y. (2003) Topics in Current Chemistry. Vol. 224, Springer, Berlin.
[19]	Zhdankin, V.V. and Stang, P.J. (2008) Chemistry of Polyvalent Iodine. Chemical Reviews, 108, 5299-5358. http://dx.doi.org/10.1021/cr800332c
[20]	Bocker, R.H. and Guengerich, F.P. (1986) Oxidation of 4-Aryl- and 4-Alkyl-Substituted 2,6-Dimethyl-3,5-bis(alkoxy- carbonyl)-1,4-dihydropyridines by Human Liver Microsomes and Immunochemical Evidence for the Involvement of a Form of Cytochrome P-450. Journal of Chemical Education, 29, 1596-1603. http://dx.doi.org/10.1021/jm00159a007
[21]	Rajput, A.P. and Rajput, S.S. (2011) A Novel Method for the Synthesis of Formyl Pyrazoles Using Vilsmeier-Haack Reaction. International Journal of Pharmacy and Pharmaceutical Sciences, 3, 346-351.
[22]	Kumar, P., Kumar, A. and Hussain, K. (2012) Iodobenzene Diacetate (IBD) Catalyzed an Quick Oxidative Aromatization of Hantzsch-1,4-dihydropyridines to Pyridines under Ultrasonic Irradiation. Ultrasonics Sonochemistry, 19, 729-735. http://dx.doi.org/10.1016/j.ultsonch.2011.12.021