Electro-Organic Synthesis: An Efficient Method for the Preparation of Nanosized Particles of Phthalazine Derivatives via One-Pot Multicomponent Reactions

Document Type: Research Paper

Authors

1 Department of chemistry, Karaj branch, Islamic Azad University, Karaj, Iran.

2 Department of Chemistry, Faculty of Sciences, Shahid Beheshti University, G. c., P. o. Box: 19396-4716, Evin, Tehran, I. R. Iran

3 chemistry and Chemical Engineering Research Center of Iran (CCERCI), PO Box 14335-186, Tehran, I.R. Iran

Abstract

Aza heterocyclic compounds are major interest for organic chemists because of their mainly pharmacological activities and clinical applications such as antianxiety, antitumor, anticonvulsant, cardiotonic and vasorelaxant. This contribution describes an electrochemical approach for the preparation of nanosized particles of phthalazine in high yields and very short reaction time. The method is based on theone-pot multicomponent reaction (MCRs) of phthalhydrazide, malononitrile and aldehydes in propanol employing undivided cell in the presence of NaBr as an electrolyte. The product was characterized, after purification, using IR, 1H NMR, 13C NMR, MS and SEM. This procedure provides a method by which nanoparticles are synthesized directly from phthalhydrazide, malononitrile and aldehydes insides of a routine protocol for the synthesis of nano particles of organic compounds in which the synthesized organic compound is transformed into nanosized particles using modern high technology, for example ultrahighpressure rapid expansion of supercritical solution, and supercritical antisolvent with enhanced mass transfer. Size reduction is a fundamental unit operation having important applications in pharmacy. It helps to improve solubility and bioavailability, reduce toxicity, enhance release, and provide better formulation opportunities for drugs.

Keywords


[1] Y. Imamura, A. Noda, T. Imamura, Y. Ono,T. Okawara, H. Noda, Life Sci. 74 (2003) 29.
[2] J. Sung Kim, H. J. Lee, M. E. Suh, H. Y. P. Choo, S. K. Lee, H. J. Park, C. Kim, S. W. Park, C. O. Lee, Biorg. Med. Chem. 12 (2004) 3683.
[3] S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappala, G. Puja, M. Baraldi, C. De Micheli, J. Med. Chem. 43(2000) 2851.
[4] Y. Nomoto, H. Obase, H. Takai, M. Teranishi, J. Nakamura, K. Kubo, Chem. Pharm. Bull. (Tokyo) 38(1990) 2179.
[5] N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama, H. Adachi, J. Med. Chem. 41(1998) 3367. [6] J. Y. Hwang, H. S. Choi, Y. D. Gong, Tetrahedron Lett. 46 (2005) 3107.
[7] H. R. Shaterian, M. Mohammadnia, Journal of Molecular Liquids 173 (2012) 55.
[8] M. R. Nabid, S. J. Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrason Sonochem. 17(2010) 159.
[9] G. M. Ziarani, N. H. Mohtasham, A. Badieib, N. Lashgarib, J. Chin. Chem. Soc. 61 (2014) 990.
[10] L. Nagarapu, R. Bantu, H. B. Mereyala,. J. Heterocyclic Chem. 46(2009) 728.
[11] H. R. Shaterian, F. Khorami, A. Amirzadeh, R. Doostmohammadi, M. Ghashang, J. Iran. Chem. Res. 2 (2009) 57.
[12] M. Sayyafi, M. Seyyedhamzeh, H. R. Khavasi, A. Bazgir, Tetrahedron 64 (2008): 2375.
[13] J. M. Khurana, D. Magoo, Tetrahedron Lett. 50 (2009) 7300.
[14] H. R. Shaterian, A. Hosseinian, M. Ghashang, Arkivoc ii (2009), 59.
[15] B. H. Rotstein, S. Zaretsky, V. Rai, A. K. Yudin, Chem. Rev. 114 (2014) 8323.
[16] R. Chmekh, I. Tapsoba, H. Medini, E. Maisonhaute, M. L. Benkhoud, K. Boujlel, Electroanal. Chem. 599 (2007) 85.
[17] A. Maleki, D. Nematollahi, Electrochem. Commun. 11 (2009) 2261.
[18] J. Azizian, A. R. Karimi, Z. Kazemizadeh, A. A. Mohammadi, M. R. Mohammadizadeh, Tetrahedron Lett. 46 (2005) 6155.
[19] J. Azizian, A. R. Karimi, E. Soleimani, A. A. Mohammadi, M. R. Mohammadizadeh, Heteroat. Chem. 17 (2008) 277.
[20] A. A. Mohammadi, J. Azizian, A. Hadadzahmatkesh, M. R. Asghariganjeh, Heterocycles 75 (2008) 947.
[21] S. Makarem, A. R. Fakhari, A. A. Mohammadi, Monatsh. Chem. 143 (2012) 1157.
[22] S. Makarem, A. R. Fakhari, A. A. Mohammadi, Ind. Eng. Chem. Res. 51 (2012) 2200.
[23] J. M. Mercero, J. M. Matxain, X. Lopez, J. E. Fowler, J. M. Ugalde, Int. J. Quantum Chem. 90 (2002) 859.
[24] E. M. Merisko-Liversidge, G. G. Liversidge, Toxicologic Pathology 36 (2008) 43.
[25] M. N. Elinson, A. S. Dorofeev, S. K. Feducovich, S. V. Gorbunov, R. F. Nasybullin, N. O. Stepanov, G. I. Nikishin, Tetrahedron Lett. 47 (2006) 7629.
[26] M. N. Elinson, A. S. Dorofeev, F. M. Miloserdov, A. I. Ilovaisky, S. K. Feducovich, P. A. Belyakov, G. I. Nikishin, Adv. Synth. Catal. 350(2008) 591.
[27] M. N. Elinson, A. I. Ilovaisky, V. M. Merkulova, D. V. Demchuk, P. A. Belyakov, Y. N. Ogibin, G. I. Nikishin, Electrochim. Acta 53 (2008) 8346.
[28] M. Elinson, V. Merkulova, A. Ilovaisky, D. Demchuk, P. Belyakov, G. Nikishin, Molecular Diversity 14 (2010) 833.