Synthesis of Some Substituted Pyrimidines Derived from 3-Acetyl Coumarin

Nabeel A.A. Al-Radha; Qassim A.H. Jaber

doi:10.14233/ajchem.2015.18925

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Issue Published : June 22, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Some Substituted Pyrimidines Derived from 3-Acetyl Coumarin

https://doi.org/10.14233/ajchem.2015.18925

Nabeel A.A. Al-Radha

Department of Chemistry, College of Education, Al-Qadisiyah University, Al Diwaniyah, Qadisiyyah Province, Iraq

Qassim A.H. Jaber

Department of Chemistry, College of Education, Al-Qadisiyah University, Al Diwaniyah, Qadisiyyah Province, Iraq

Corresponding Author(s) : Nabeel A.A. Al-Radha

nabeel1959@yahoo.com; kas888alshibany777@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 10 (2015): Vol 27 Issue 10
Article Published : June 22, 2015

Abstract

This study targets mainly the synthesis of a number of derivatives of coumarin containing ring pyrimidin-2-one substitutes different aromatic rings, taking advantage of the Biginelli reaction which includes the reaction of 3-acetyl coumarin with suitable aromatic aldehydes and urea in the presence of AlCl₃ and absolute ethanol as a solvent. It has been indicated that the biological activity is important and diverse to these kinds of compounds, which is the preparation of compound 3-acetyl coumarin (7) to be used as a compound base. The compounds having heterocyclic ring are expected to have various important biological and therapeutic applications. This proves structural formulae for each of new synthetic compounds on the basis of chemical reactions, analysis of the elements, the infrared spectra and nuclear magnetic resonance (¹H NMR and ¹³C NMR).

Keywords

Coumarin derivatives Substituted pyrimidines 4 4,3-Dihydro-(4-aryl-6-coumarin)pyrimidin-2-one

A.A. Al-Radha, N., & A.H. Jaber, Q. (2015). Synthesis of Some Substituted Pyrimidines Derived from 3-Acetyl Coumarin. Asian Journal of Chemistry, 27(10), 3687–3691. https://doi.org/10.14233/ajchem.2015.18925

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References

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C.O. Kappe, Tetrahedron, 49, 6937 (1993); doi:10.1016/S0040-4020(01)87971-0.
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B.H. Lee, J.H. Shin and M.K. Lim, Bull. Korean Chem. Soc., 18, 734 (1997).
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References

E.A. Gunnewegh, A.J. Hoefnagel, R.S. Downing and H. van Bekkum, Recl. Trav. Chim. Pays Bas, 115, 226 (1996); doi:10.1002/recl.19961150407.

W.-C. Sun, K.R. Gee and R.P. Haugland, Bioorg. Med. Chem. Lett., 8, 3107 (1998); doi:10.1016/S0960-894X(98)00578-2.

J. Oyamada, C. Jia, Y. Fujiwara and T. Kitamura, Med.Chem. Lett., 14, 380 (2002); doi:10.1246/cl.2002.380.

R.D.H. Murray, J. Medez and S.A. Brown, The Natural Coumarins: Occurrence, Chemistry and Biochemistry, Wiley, New York, p. 68 (1982).

F. Hueso-Ureña, N.A. Illán-Cabeza, M.N. Moreno-Carretero, J.M. Martínez-Martos and M.J. Ramírez-Expósito, J. Inorg. Biochem., 94, 326 (2003); doi:10.1016/S0162-0134(03)00025-4.

H.S. Basavaraja, K.V. Jayadevaiah and M.M. Hussain, J. Pharm. Sci. Res., 12, 5 (2010).

R. Patel, K. Desai and Chikhalia, J. Indian Chem. Soc., 80, 138 (2003).

K. Desai, R. Patel and Chikhalia, Indian J. Chem., 45B, 773 (2006).

A.E.-G.E. Amr, N.M. Sabry and M.M. Abdulla, Monatsh. Chem., 138, 699 (2007); doi:10.1007/s00706-007-0651-0.

N. Fujiwara, T. Nakajima, Y. Ueda, H. Fujita and H. Kawakami, Bioorg. Med. Chem., 16, 9804 (2008); doi:10.1016/j.bmc.2008.09.059.

L. Ballell, R.A. Field, G.A.C. Chung and R.J. Young, Bioorg. Med. Chem. Lett., 17, 1736 (2007); doi:10.1016/j.bmcl.2006.12.066.

E. Wagner, K. Al-Kadasi, M. Zimecki and W. Sawka-Dobrowolska, Eur. J. Med. Chem., 43, 2498 (2008); doi:10.1016/j.ejmech.2008.01.035.

K. Gorlitzer, S. Herbig and R.D. Walter, Pharmazie, 52, 670 (1997).

I.V. Ukrainets, I.A. Tugaibei, N.L. Bereznyakova, V.N. Kravchenko and A.V. Turov, Chem. Heterocycl. Comp., 44, 565 (2008); doi:10.1007/s10593-008-0076-7.

S.Q. Wang, L. Fang, X.J. Liu and K. Zhao, Chin. Chem. Lett., 15, 885 (2004).

C.O. Kappe, Tetrahedron, 49, 6937 (1993); doi:10.1016/S0040-4020(01)87971-0.

(a) H. Wamhoff, J. Dzenis and K. Hirota, Adv. Heterocycl. Chem., 55, 129 (1992); doi:10.1016/S0065-2725(08)60222-6; (b) Z. Seferoglu, ARKIVOC, 42 (2009); doi:10.3998/ark.5550190.0010.705.

P.G. Ellis, in ed.: E.C. Taylor, The Chemistry of Heterocyclic Dyes; Wiley Interscience: Chichester; vol. 47; pp. 1-20 (1987).

E. Coats, W.R. Glave and C. Hansch, J. Med. Chem., 13, 913 (1970); doi:10.1021/jm00299a027.

B.H. Lee, J.H. Shin and M.K. Lim, Bull. Korean Chem. Soc., 18, 734 (1997).

J.L. Bernier, J.P. Henichart, V. Warin, C. Trentesaux and J.C. Jardillier, J. Med. Chem., 28, 497 (1985); doi:10.1021/jm00382a020.

A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry, Pergamon Press: Oxford, edn 3, pp. 57 (1984).

S. Anil and K. Sanjay, Indian J. Chem., 46B, 1690 (2007).

H.K.A. Al-Chriti, M. Sc. Thesis, Al-Kufa University, Iraq (2013).

B.S. Jayashree, S. Arora and K.N. Venugopala, Asian J. Chem., 20, 1 (2008).

F. Sweet and J.D. Fissekis, J. Am. Chem. Soc., 95, 8741 (1973); doi:10.1021/ja00807a040.

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Synthesis of Some Substituted Pyrimidines Derived from 3-Acetyl Coumarin

Corresponding Author(s) : Nabeel A.A. Al-Radha

Abstract

Keywords

Full Article

Download Citation

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