IJOC  Vol.3 No.1 , March 2013
Synthesis of 3-Aryl Coumarin Derivatives Using Ultrasound

Coumarins occupy an important place in the realm of natural products and synthetic organic chemistry. A fast and highly efficient green method for synthesizing 3-aryl coumarin derivatives from salicylaldehyde and phenyl acetyl chloride in the presence of tetrahydrofuran and K2CO3 using ultrasound irradiation is reported. Ultrasound assisted reactions have resulted in better yields and faster reaction time of the desired products than when prepared under conventional conditions. The resulting coumarin derivatives were characterized by IR spectrum.

Cite this paper
S. Sripathi and K. Logeeswari, "Synthesis of 3-Aryl Coumarin Derivatives Using Ultrasound," International Journal of Organic Chemistry, Vol. 3 No. 1, 2013, pp. 42-47. doi: 10.4236/ijoc.2013.31004.
[1]   A. J. Fry and D. Herr, “Reduction of α, α’-Dibromo Ketones by Ultrasonically Dispersed Mercury in Protic Solvents,” Tehrahedron Letters, Vol. 19, No. 20, 1979, pp. 1721-1724. doi:10.1016/0040-4039(78)80026-4

[2]   J.-L. Luche, C. Petrier, J.-P. Lansard and A. E. Greene, “Ultrasound in Organic Synthesis: A Simplified Preparation of Diarylzinc Reagents and Their Conjugate Addition to Alpha-Enones,” Journal of Organic Chemistry, Vol. 48, No. 21, 1983, pp. 3837-3839. doi:10.1021/jo00169a055

[3]   J. Li, L. J. Li, T. S. Li and J. Z. Wang, “Ultrasound-Promoted Synthesis of 5-Substituted and 5, 5-Disubstituted Hydantoins,” Indian Journal of Chemistry, Vol. 37, No. 3, 1998, pp. 298-300.

[4]   M. Kidwai, “Green Chemistry in India,” Pure and Applied Chemistry, Vol. 73, No. 8, 2001, pp. 1261-1263. doi:10.1351/pac200173081261

[5]   K. Wei, H.-T. Gao and W.-D. Z. Li, “Facile Synthesis of Oxabicyclic Alkenes by Ultra Sonication-Promoted Diels Alder Cycloaddition of Furano Dienes,” The Journal of Organic Chemistry, Vol. 69, No. 17, 2004, pp. 5763-5765. doi:10.1021/jo049210a

[6]   S. Moon, L. Duchin and J. V. Cooney, “Application of Ultrasound to Organic Reactions: Ultrasonic Catalysis on Hydrolysis of Carboxylic acid Esters,” Tetrahedron Letters, Vol. 20, No. 41, 1979, pp. 3917-3920. doi:10.1016/S0040-4039(01)86464-9

[7]   T. J. Mason, “Ultrasound in Synthetic Organic Chemistry,” Chemical Society Reviews, Vol. 26, 1997, pp. 443- 451. doi:10.1039/cs9972600443

[8]   W. Oppolzer and P. Schneider, “Practical Preparation and Metallo-Ene Reactions of (2-Alkenylallyl)-magnesium Chlorides: Comparative Study of Magnesium Activation,” Tetrahedron Letters, Vol. 25, No. 31, 1984, pp. 3305-3308. doi:10.1016/S0040-4039(01)81370-8

[9]   B. H. Han and P. Boudjouk, “Organic Sonochemistry. Ultrasound-Promoted Coupling of Organic Halides in the Presence of Lithium Wire,” Tetrahedron Letters, Vol. 22, No. 29, 1981, pp. 2757-2758. doi:10.1016/S0040-4039(01)90544-1

[10]   B. H. Han and P. Boudjouk, “Organic Sonochemistry Ultrasound-Promoted Reaction of Zinc with α,α’-dibromo-o-xylene. Evidence for Facile Generation of o-Xylene,” The Journal of Organic Chemistry, Vol. 47, No. 4, 1982, pp. 751-752. doi:10.1021/jo00343a035

[11]   D. I. Brahmbhatt, C. N. Patel, V. P. Pandya and M. A. Patel, “Synthesis of Some 3-Phenyl-4-methyl-6-(6-aryl- pyridin-2-yl) and 3-Phenyl-4-methyl-6-(4,6-diarylpyridin- 2-yl) Coumarins,” The Journal of Organic Chemistry, Vol. 43, 2004, pp. 2228-2230.

[12]   V. K. Ahluwalia and S. Mehta, “Removal of 4-Hydroxy Group in 4-Hydroxy-3-phenylcoumarins: Formation of 3-Phenylcoumarins,” The Journal of Organic Chemistry, Vol. 16, 1978, pp. 977-979.

[13]   D. Bogdal, “Coumarins: Fast Synthesis by Knoevenagal Condensation under Microwave Irradiation,” Journal of Chemical Research, Synopses, Vol. 8, 1998, pp. 468-469. doi:10.1039/a801724g

[14]   V. Singh, J. Singh, K. P. Kaur and G. L. Kad, “Acceleration of the Pechmann Reaction by Microwave Irradiation: Application to the Preparation of Coumarins,” Journal of Chemical Research, Vol. 2, 1997, pp. 58-59. doi:10.1039/a605672e

[15]   G. Tocco, M. Begala, G. Delogu, G. Meli, C. Picciau and G. Podda, “Soluble Polymer-Supported Synthesis of 4-Methyl Coumarin on Modified Poly(ethylene glycol)s,” Synlett, Vol. 8, 2005, pp. 1296-1300. doi:10.1055/s-2005-865231

[16]   I. P. Beletskaya, O. G. Ganina, A. V. Tsvetkov, A. Yu. Fedoror and J.-P. Finet, “Synthesis of 4-Heteroaryl-substituted Coumarins by Suzuki Cross-Coupling Reactions,” Synlett, Vol. 15, 2004, pp. 2797-2799.

[17]   K. B. L. Mathur and K. N. Sawhney, “Studies on Some Structural Aspects of 4-Hydroxy Coumarin: Further Extension of Meerwein’s Diazo Reaction and a Substitution Reaction Involving 2-Chloro-2-methylbutyne,” Indian Journal of Chemistry, Vol. 14, 1976, pp. 518-521.

[18]   M. Kotani, K. Yamamoto, J. Oymada, Y. Fujiwara and T. Kitamura, “A Convenient Synthesis of Coumarins by Palladi-um(II)-Catalyzed Reaction of Phenols with Pro- piolic Acids,” Synthesis, Vol. 9, 2004, pp. 1466-1470. doi:10.1055/s-2004-822360

[19]   M. J. Matos, S. Vazquez-Rodriguez, F. Borges and E. Uriarte, “Alternative Methodologies for the Synthesis of Substituted 3-Arylcoumarins: Perkin Reactions and Palladium-Catalyzed Synthesis,” 14th International Electronic Conference on Synthetic Organic Chemistry (ECSOC-14), 1-30 November 2010.

[20]   L. A. Shastri, M. Ghate, and M. V. Kulkarni, “Dual Fluorescence and Biological Evaluation of Paracetamol Ethers from 4-Bromomethyl Coumarins,” Indian Journal of Chemistry, Vol. 43, No. 11, 2004, pp. 2416-2422.

[21]   D. Olmedo, R. Sancho, L. M. Bedoya, J. L. Lopez-Perez, E. del Olmo, E. Munoz, J. Alcami, M. P. Gupta and A. San Feliciano, “3-Phenylcoumarins as Inhibitors of HIV-1 Replication,” Molecules, Vol. 17, No. 8, 2012, pp. 9245-9257. doi:10.3390/molecules17089245

[22]   J. Yang, G.-Y. Liu, F. Dai, X.-Y. Cao, Y.-F. Kang, L.-M. Hu, J.-J. Tang, X.-Z. Li, Y. Li, X.-L. Jin and B. Zhou, “Synthesis and Biological Evaluation of Hydroxylated 3-Phenylcoumarins as Antioxidants and Anti-Proliferative Agents,” Bioorganic & Medicinal Chemistry Letters, Vol. 21, No. 21, 2011, pp. 6420-6425. doi:10.1016/j.bmcl.2011.08.090

[23]   K. V. Sashidhara, A. Kumar, M. Chatterjee, K. B. Rao, S. Singh, A. K. Verma and G. Palit, “Discovery and Synthesis of Novel 3-Phenylcoumarin Derivatives as Antidepressant Agents,” Bioorganic & Medicinal Chemistry Letters, Vol. 21, No. 7, 2011, pp. 1937-1941. doi:10.1016/j.bmcl.2011.02.040

[24]   B. S. Joshi, N. Viswanathan, C. L. Kaul and R. S. Grewal, “Evaluation of Some Naturally Occurring & Synthetic Coumarins for Hypotensive Activity,” Indian Journal of Chemistry, Vol. 19, 1980, pp. 495-499.

[25]   A. Arnoldi, G. Farina, R. Galli, L. Merlini and M. G. Parrino, “Analogs of Phytoalexins. Synthesis of Some 3-Phenylcoumarins and Their Fungicidal Activity,” Journal of Agricultural and Food Chemistry, Vol. 34, No. 2, 1986, pp. 185-188. doi:10.1021/jf00068a007

[26]   M. J. Matos, D. Vina, C. Picciau, F. Orallo, L. Santana and E .Uriarte, “Synthesis and Evaluation of 6-Methyl-3- phenylcoumarins as Potent and Selective MAO-B Inhibitors,” Bioorganic & Medicinal Chemistry Letters, Vol. 19, No. 17, 2009, pp. 5053-5055. doi:10.1016/j.bmcl.2009.07.039