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This work is licensed under a Creative Commons Attribution 4.0 International License.
Modified Biginelli Reaction: Synthesis of Pyrimidoquinoline Derivatives
Corresponding Author(s) : S. Thamarai Selvi
Asian Journal of Chemistry,
Vol. 31 No. 6 (2019): Vol 31 Issue 6
Abstract
Compounds having quinolone and pyrimidine skeleton plays an important role in the medicinal chemistry. The objective of the present work was to modify the Biginelli reaction by using heterocylic ketones under microwave condition. We have demonstrated new synthetic route of quinolone fused 1,4-dipyrimidines by the reaction of 6-methyl-4-hyrdoxyquinolin-2(1H)-one (1), substituted aromatic aldehydes (2a-g) with phenyl urea (3). The structure of these newly synthesized compounds was characterized IR, NMR, Mass spectral and elemental analysis.
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- S. Caddick, Tetrahedron, 51, 10403 (1995); https://doi.org/10.1016/0040-4020(95)00662-R.
- M.B. Gawande, S.N. Shelke, R. Zboril and R.S. Varma, Acc. Chem. Res., 47, 1338 (2014); https://doi.org/10.1021/ar400309b.
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- V. Nadaraj and S.T. Selvi, Indian J. Chem., 46B, 1203 (2007).
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- S.T. Selvi, V. Nadaraj, S. Mohan, R. Sasi and M. Hema, Bioorg. Med. Chem., 30, 3896 (2006); https://doi.org/10.1016/j.bmc.2006.01.048.
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- S.A.F. Rostom and A.A. Bekhit, Eur. J. Med. Chem., 92, 712 (2015); https://doi.org/10.1016/j.ejmech.2015.01.023.
- E. Aydemir and S. Kaban, Asian J. Chem., 30, 1460 (2018); https://doi.org/10.14233/ajchem.2018.21180.
- S. Kantevari, T. Yempala, G. Surineni, B. Sridhar, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 46, 4827 (2011); https://doi.org/10.1016/j.ejmech.2011.06.014.
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- E. Rajanarendar, M.N. Reddy, K.R. Murthy, K.G. Reddy and S. Raju, Bioorg. Med. Chem., 20, 6052 (2010); https://doi.org/10.1016/j.bmcl.2010.08.060.
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- S. Chitra, D. Devanathan and K. Pandiarajan, Eur. J. Med. Chem., 45, 367 (2010); https://doi.org/10.1016/j.ejmech.2009.09.018.
- C.O. Kappe, Eur. J. Chem., 35, 1043 (2000); https://doi.org/10.1016/S0223-5234(00)01189-2.
- M.B. Nawrozkij, D. Rotili, D. Tarantino, G. Botta, A.S. Eremiychuk, I. Musmuca, R. Ragno, A. Samuele, S. Zanoli, M. Armand-Ugón, I. Clotet-Codina, I.A. Novakov, B.S. Orlinson, G. Maga, J.A. Esté, M. Artico and A. Mai, J. Med. Chem., 51, 4641 (2008); https://doi.org/10.1021/jm800340w.
- K. Rana, A. Arora, S. Bansal and R. Chawla, Indian J. Pharm. Sci., 76, 339 (2014); https://doi.org/10.4103/0250-474X.139929.
- S.M. Sondhi, M. Johar, S. Rajvanshi, S.G. Dastidar, R. Shukla, R. Raghubir and J.W. Lown, Aust. J. Chem., 54, 69 (2001); https://doi.org/10.1071/CH00141.
- V. Nadaraj, S.T. Selvi, S. Mohan and T.D. Thangadurai, Med. Chem. Res., 21, 2911 (2012); https://doi.org/10.1007/s00044-011-9811-1.
- V. Nadaraj, S.T. Selvi and T.D. Thangadurai, J. Pharm. Res., 4, 541 (2011).
- V. Nadaraj, S.T. Selvi, M. Abriami and T.D. Thangadurai, Res. J. Recent Sci., 3, 370 (2014).
- V. Nadaraj, S.T. Selvi, M. Abriami and T.D. Thangadurai, Res. J. Pharm. Biol. Chem. Sci., 6, 901 (2015).
- P. Shanmugam, C. Sebastein and P.T. Perumal, Indian J. Chem., 43B, 135 (2004).
- Z. Hassani, M.R. Islami and M. Kalantari, Bioorg. Med. Chem. Lett., 16, 4479 (2006); https://doi.org/10.1016/j.bmcl.2006.06.038.
References
S. Caddick, Tetrahedron, 51, 10403 (1995); https://doi.org/10.1016/0040-4020(95)00662-R.
M.B. Gawande, S.N. Shelke, R. Zboril and R.S. Varma, Acc. Chem. Res., 47, 1338 (2014); https://doi.org/10.1021/ar400309b.
C.O. Kappe and D. Dallinger, Nat. Drug. Disc. Rev., 5, 51 (2006); https://doi.org/10.1038/nrd1926.
P. Acosta, B. Insuasty, A. Ortiz, R. Abonia, M. Sortino, S.A. Zacchino and J. Quiroga, Arab. J. Chem., 9, 481 (2016); https://doi.org/10.1016/j.arabjc.2015.03.002.
V. Nadaraj, S.T. Selvi and S. Mohan, Eur. J. Med. Chem., 44, 976 (2009); https://doi.org/10.1016/j.ejmech.2008.07.004.
V. Nadaraj and S.T. Selvi, Indian J. Chem., 46B, 1203 (2007).
V. Nadaraj and S.T. Selvi, Res. J. Chem. Environ., 17, 46 (2013).
S.T. Selvi, V. Nadaraj, S. Mohan, R. Sasi and M. Hema, Bioorg. Med. Chem., 30, 3896 (2006); https://doi.org/10.1016/j.bmc.2006.01.048.
V. Nadaraj, S.T. Selvi, H.P. Bai, S. Mohan and T.D. Thangadurai, Med. Chem. Res., 21, 2902 (2012); https://doi.org/10.1007/s00044-011-9810-2.
V. Nadaraj, S.T. Selvi and R. Sasi, ARKIVOC, 2006, 82 (2006); https://doi.org/10.3998/ark.5550190.0007.a11.
V. Nadaraj and S.T. Selvi, Orient. J. Chem., 25, 549 (2009).
V. Nadaraj and S.T. Selvi, Int. J. ChemTech Res., 2, 1 (2011).
D.S. Ermolat’ev, V.L. Alifanov, V.B. Rybakov, E.V. Babaev and E.V. Van der Eycken, Synthesis, 2008, 2083 (2008); https://doi.org/10.1055/s-2008-1078444.
N.C. Desai and A.M. Dodiya, Arab. J. Chem., 7, 906 (2014); https://doi.org/10.1016/j.arabjc.2011.08.007.
S.A.F. Rostom and A.A. Bekhit, Eur. J. Med. Chem., 92, 712 (2015); https://doi.org/10.1016/j.ejmech.2015.01.023.
E. Aydemir and S. Kaban, Asian J. Chem., 30, 1460 (2018); https://doi.org/10.14233/ajchem.2018.21180.
S. Kantevari, T. Yempala, G. Surineni, B. Sridhar, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 46, 4827 (2011); https://doi.org/10.1016/j.ejmech.2011.06.014.
S. Asghari, S. Ramezani and M. Mohseni, Chin. Chem. Lett., 25, 431 (2014); https://doi.org/10.1016/j.cclet.2013.12.010.
E. Rajanarendar, M.N. Reddy, K.R. Murthy, K.G. Reddy and S. Raju, Bioorg. Med. Chem., 20, 6052 (2010); https://doi.org/10.1016/j.bmcl.2010.08.060.
A.A. Joshi, S.S. Narkhede and C.L. Viswanathan, Bioorg. Med. Chem. Lett., 15, 73 (2005); https://doi.org/10.1016/j.bmcl.2004.10.037.
A. Chilin, G. Marzaro, C. Marzano, L.D. Via, M.G. Ferlin, G. Pastorini and A. Guiotto, Bioorg. Med. Chem., 17, 523 (2009); https://doi.org/10.1016/j.bmc.2008.11.072.
E. Rajanarendar, M. Nagi Reddy, S. Rama Krishna, K. Rama Murthy, Y.N. Reddy and M.V. Rajam, Eur. J. Med. Chem., 55, 273 (2012); https://doi.org/10.1016/j.ejmech.2012.07.029.
S. Chitra, D. Devanathan and K. Pandiarajan, Eur. J. Med. Chem., 45, 367 (2010); https://doi.org/10.1016/j.ejmech.2009.09.018.
C.O. Kappe, Eur. J. Chem., 35, 1043 (2000); https://doi.org/10.1016/S0223-5234(00)01189-2.
M.B. Nawrozkij, D. Rotili, D. Tarantino, G. Botta, A.S. Eremiychuk, I. Musmuca, R. Ragno, A. Samuele, S. Zanoli, M. Armand-Ugón, I. Clotet-Codina, I.A. Novakov, B.S. Orlinson, G. Maga, J.A. Esté, M. Artico and A. Mai, J. Med. Chem., 51, 4641 (2008); https://doi.org/10.1021/jm800340w.
K. Rana, A. Arora, S. Bansal and R. Chawla, Indian J. Pharm. Sci., 76, 339 (2014); https://doi.org/10.4103/0250-474X.139929.
S.M. Sondhi, M. Johar, S. Rajvanshi, S.G. Dastidar, R. Shukla, R. Raghubir and J.W. Lown, Aust. J. Chem., 54, 69 (2001); https://doi.org/10.1071/CH00141.
V. Nadaraj, S.T. Selvi, S. Mohan and T.D. Thangadurai, Med. Chem. Res., 21, 2911 (2012); https://doi.org/10.1007/s00044-011-9811-1.
V. Nadaraj, S.T. Selvi and T.D. Thangadurai, J. Pharm. Res., 4, 541 (2011).
V. Nadaraj, S.T. Selvi, M. Abriami and T.D. Thangadurai, Res. J. Recent Sci., 3, 370 (2014).
V. Nadaraj, S.T. Selvi, M. Abriami and T.D. Thangadurai, Res. J. Pharm. Biol. Chem. Sci., 6, 901 (2015).
P. Shanmugam, C. Sebastein and P.T. Perumal, Indian J. Chem., 43B, 135 (2004).
Z. Hassani, M.R. Islami and M. Kalantari, Bioorg. Med. Chem. Lett., 16, 4479 (2006); https://doi.org/10.1016/j.bmcl.2006.06.038.