Synthesis, Spectroscopic and Crystal Structure Studies on Ethyl 5,7-Dimethyl Coumarin-4-Acetate

Kiran K. Pujar, G. N. Anilkumar, Manohar V. Kulkarni

Department of Chemistry, Karnatak University, Dharwad, India.
M S Ramaiah Institute of Technology, Department of Physics, Bangalore, India.

DOI: 10.4236/csta.2013.22012                

Abstract

Ethyl ester of 5,7-dimethyl coumarin-4-acetic acid has been synthesized from 3,5-Xylenol in a two step sequence of reaction involving Pechmann cyclisation and acid catalyzed esterification. The title compound 2 crystallizes in Monoclinic form, space group P 1 21/c 1, with a = 8.6248(4) ?, b = 18.9103(8) , c = 8.4204(4)?, β = 101.241(2）?, V = 1347.00(11) ?, D cal = 1.283 Mg/cm3, Z = 4. The molecule is stabilized by intermolecular C-H … O bonds.

Keywords

Coumarin-4-Acetic acid Ethyl Ester; X-Ray Diffraction

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	M. V. Kulkarni, G. M. Kulkarni, C. H. Lin and C. M. Sun, “Coumarins and 1-Azacoumarins as Biodynamic Agents,” Current Medicinal Chemistry, Vol. 13, No. 23, 2006, pp. 2795-2818. doi:10.2174/092986706778521968
[2]	S. Roseman, C. F. Heubuer, R. Pankratz and K. P. Link, “Studies on 4-Hydroxy Coumarins. XVI. The Metabolism of 4-Hydroxy Coumarins in the Dog,” Journal of the American Chemical Society, Vol. 76, No. 6, 1954, pp. 16501652. doi:10.1021/ja01635a055
[3]	P. Laurin, D. Ferroud, L. Schiol, M. Klich, C. DupuisHamelin, P. Mauvais, P. Lassaigne, A. Bonnefoy and B. Musicki, “Structure-Activity Relationship in Two Series of Aminoalkyl Substituted Coumarin Inhibitors of Gyrase B,” Bioorganic and Medicinal Chemistry Letters, Vol. 9, No. 19, 1999, pp. 2875-2880.
[4]	M. V. Kulkarni and V. D. Patil, “Studies on Coumarins (Part 1),” Archiv der Pharmazie, Vol. 314, No. 8, 1981, pp. 708-711. doi:10.1002/ardp.19813140810
[5]	S. S. Hanmantgad, M. V. Kulkarni and V. D. Patil, “Synthesis and Biological Activity of Some 4-(SulphonamidoMethyl)-Coumarins,” Indian Journal of Chemistry, Vol. 24B, No. 4, 1985, pp. 459-461.
[6]	M. Ghate and M. V. Kulkarni, “Synthesis of Vanillin Ethers from 4-Bromomethyl Coumarins as Anti-Inflammatory Agents,” European Journal of Medicinal Chemistry, Vol. 38, No. 3, 2003, pp. 297-302. doi:10.1016/S0223-5234(03)00016-3
[7]	M. Basanagouda, V. B. Jadhav, M. V. Kulkarni and R. Nagendra Rao, “Computer Aided Prediction of Biological Activity Spectra: Study of Correlation between Predicted and Observed Activities for Coumarin-4-Acetic Acids,” Indian Journal of Pharmaceutical Sciences, Vol. 73, No. 1, 2011, pp. 88-92.
[8]	V. B. Jadhav, S. K. Nayak, T. N. Row and M. V. Kulkarni, “Synthesis, Structure and DNA Cleavage Studies of Coumarin Analogues of Tetrahydroisoquinoline and Protoberberine Alkaloids,” European Journal of Medicinal Chemistry, Vol. 45, No. 9, 2010, pp. 3575-3580.
[9]	K. Sivakumar, F. Jesurethinam, K. Subramanian and S. Natarajan, “7-Hydroxy-4-Coumarin Acetic Acid Monohydrate,” Acta Crystallographica Section C, Vol. 46, 1990, pp. 1663-1665. doi:10.1107/S0108270189011522
[10]	S. Naveen, S. M. Anandwalkar, et al., “7,8-Dimethyl Coumarin 4-Acetic Acid Ethyl Esters,” Analytical Sciences, Vol. 22, 2006, pp. X173-X174.
[11]	I. Fujii, Y. Mano and N. Hirayama, “Crystal of 4-Ethoxycoumarin” Analytical Science, Vol. 21, 2005, pp. x7-x8
[12]	N. M. Mahabaleshwaraiah, K. M. Kumar, O. Kotresh, W. F. A. Al-Eryani and H. C. Devarajgowda, “(6-Methoxy-2Oxo-2H-Chromen-4-yl)Methylpyrrolidine-1-Carbodithiate,” Acta Crystallographica, Vol. E68, No. 5, 2012, p. 1566.
[13]	P. Deslongchamps, U. O. Cheriyan, J. P. Pradere, P. Soucy and R. J. Taillefer, “Hydrolysis and Isomerization of syn Unsymmetrical N,N-Dialkylated Immidate Salts. Experimental Evidence for Conformational Changes and for Stereo Electronically Controlled Cleaves in Hemi-Orthoamide Tetrahedral Intermediates,” Nouveau Journal de Chimie, Vol. 3, No. 2, 1979, pp. 343-350.
[14]	S. C. Laskowski and R. O. Clinton, “Coumarins. II. Derivative of Coumarins-3and -4-Acetic Acids,” Journal of the American Chemical Society, Vol. 72, No. 9, 1950, pp. 3987-3991. doi:10.1021/ja01165a043