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Copyright (c) 2014 A. Arrahman1, H. Suryadi2, A. Yanuar1
This work is licensed under a Creative Commons Attribution 4.0 International License.
Microwave Assisted Synthesis of Pyridin-1-ium Salt of 6-Nitroquinazolin-4-one and its 6-Amino Analog under Ultrasonic Irradiation
Corresponding Author(s) : A. Arrahman1
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
The new compounds of quinazolin-4-one derivative i.e., 2-methyl-6-nitroquinazolin-4-one substituted pyridin-1-ium salt at methyl group and its 6-amino analog have been synthesized. Microwave irradiation of solution of 2-bromomethyl-6-nitroquinazolin-4-one and pyridine in acetonitrile for 3 min afforded 1-[(6-nitroquinazolin-4-one-2-yl)methyl]pyridin-1-ium bromide; and nitro reduction of the product with iron in ethanol/acetic acid/water under ultrasonic irradiation afforded 1-[(6-aminoquinazolin-4-one-2-yl)methyl]pyridin-1-ium bromide. The structure of the synthesized compounds were confirmed on the basis of FT-IR, 1H NMR and 13C NMR data.
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- D.J. Connolly, D. Cusack, T.P. O'Sullivan and P.J. Guiry, Tetrahedron, 61, 10153 (2005).
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- Y. Ju and R.S. Varma, Green Chem., 6, 219 (2004).
- C.O. Kappe and D. Dallinger, Drug Discovery, 5, 51 (2006).
- A.B. Gamble, J. Garner, C.P. Gordon, S.M.J. O'Conner and P.A. Keller, Synth. Commun., 37, 2777 (2007).
- S.S. Kotgire, S.K. Mahajan, S.V. Amrutkar and U.D. Bhagat, J. Pharm. Sci. Res., 2, 518 (2010).
- M.S. Ranawat, S.V. Amrutkar and P. Phargharmol, Int. J. Drug Design Discovery, 2, 452 (2011).
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References
D.J. Connolly, D. Cusack, T.P. O'Sullivan and P.J. Guiry, Tetrahedron, 61, 10153 (2005).
S.R. Pattan, Indian J. Chem., 45B, 1778 (2006).
M. Srivastav, MD. Salahuddin and S.M. Shantakumar, E-J. Chem., 6, 1055 (2009).
S. Hameed, M. Saeed, A. Khan, M. Ahmed, S.S. Nizami and M.H. Kazmi, J. Islamic Ac. Sci., 7, 26 (1994).
R.N. Jayatissa, R.P. Perera, C.M. Hettiarachchi and P.M. Weerawarna, Indian J. Microbiol., 52, 83 (2012).
V. Alptüzün, S. Parlar, H. Tasli and E. Erciyas, Molecules, 14, 5203 (2009).
Y. Ju and R.S. Varma, Green Chem., 6, 219 (2004).
C.O. Kappe and D. Dallinger, Drug Discovery, 5, 51 (2006).
A.B. Gamble, J. Garner, C.P. Gordon, S.M.J. O'Conner and P.A. Keller, Synth. Commun., 37, 2777 (2007).
S.S. Kotgire, S.K. Mahajan, S.V. Amrutkar and U.D. Bhagat, J. Pharm. Sci. Res., 2, 518 (2010).
M.S. Ranawat, S.V. Amrutkar and P. Phargharmol, Int. J. Drug Design Discovery, 2, 452 (2011).
C.M. Gupta, A.P. Bhaduri and N.M. Khanna, J. Med. Chem., 11, 392 (1968).
Y. Kabri, P. Verhaeghe, A. Gellis and P. Vanelle, Molecules, 15, 2949 (2010).
S. Sastradi, B.P, Maggadani and Hayun, Synthesis of Nitro Derivatives of 3-(4-Chlorophenyl)-2-methyl-4(3H)-quinazolinon, Proceeding ICICS-2013, Yogyakarta, Oct. 22-23 (2013).
R.M. Silverstein, G.C. Basseler and T.C. Morrill, Spectrometric Identi-fication of Organic Compound, JohnWiley & Sons, Inc., New York: edn. 5 (1991).