Document Type : Original Paper
Authors
1 Tehran North Branch, Islamic Azad University
2 Tehran University of Medical Sciences
Abstract
In this paper, the synthesis of various enaminones from the reaction of 3-aminocoumarin and ethyl-2,4-dioxo-4-arylbutanoate in the presence of p-toluene sulfonic acid is reported. The reaction was examined under different solvents and catalytic systems, which clearly proved the importance of acidic catalyst in this organic transformation. This work was also accompanied by density functional theory (DFT) studies to justify the formation of final products.
Keywords
Main Subjects
- Jain P.K. and Joshi H. Coumarin: chemical and pharmacological profile. Appl. Pharm. Sci. 2: 236-240 (2012).
- Murray R.D.H. In Progress in the Chemistry of Organic Natural Products. Springer: Wien-New York. 72: 1-119 (1997).
- Charitos C., Kokotos G. and Tzougraki C. Bifunctional coumarin derivatives in solution and solid phase synthesis of fluorogenic enzyme substrates. Heterocycl. Chem. 38: 153-158 (2001).
- Borges F., Roleira F., Milhazes N., Santana L. and Uriarte E. Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity. Med. Chem. 12: 887-916 (2005).
- Gurumurthy Ch., Fatima N., Reddy G.N., Ganesh Kumar C., Sabitha G. and Ramakrishna, K.V.S. A diastereoselective synthesis of tetrahydro- and dihydro-pyrido[2,3-c]coumarin derivatives via a one-pot three-component Povarov reaction catalyzed by bismuth(III) chloride. Med. Chem. Lett. 26: 5119-5125 (2016).
- Chen Z., Hua L. and Peng F. Efficient Synthesis of Functionalized Pyrido[2,3-c]coumarin Derivatives by a One-Pot Three-Component Reaction. Synlett, 27: 1888-1892 (2016).
- Khan A.T. and Das D.K. Michael Initiated Ring Closure (MIRC) reaction on in situ generated benzylidenecyclohexane-1,3-diones for the construction of chromeno[3,4-b]quinoline derivatives. Tetrahedron Lett. 53: 2345-2351 (2012).
- Madhura V., Kulkarni M.V., Shah A. and Alagawadi K.R. Mannich Reaction as a New Route for the Synthesis of Tetrahydro Pyrimido Benzimidazolyl Coumarins. Heterocycl. Chem. 51: 1705-1711 (2014).
- Yu T., Peng Z., Yuling Z., Hui Z., Jing M. and Duowang F. Synthesis, characterization and high-efficiency blue electroluminescence based on coumarin derivatives of 7-diethylaminocoumarin-3-carboxamide. Electron. 10: 653-660 (2009).
- Asish R., Arunima M. and Raghunath S. Synthesis of biologically potent new 3-(heteroaryl) aminocoumarin derivatives via Buchwald–Hartwig C–N coupling. Tetrahedron Lett. 51: 1099-1102 (2010).
- Amit A., Jamie K., Chad C., Natasha D. and Graham J. Hydrolysis-free synthesis of 3-aminocoumarins. Tetrahedron Lett. 48: 5077-5080 (2007).
- Viña D., Matos M.J., Yáñez M., Santana L. and Uriarte E. 3-Substituted coumarins as dual inhibitors of AChE and MAO for the treatment of Alzheimer's disease. Chem. Comm. 3: 213-218 (2010).
- Kadhum A.A., Mohamad A.B., Al-Amiery A.A. and Takriff M.S. Antimicrobial and antioxidant activities of new metal complexes derived from 3-aminocoumarin. Molecules, 16: 6969-6984 (2011).
- Hamama W.S., Ibrahim M.E., Metwalli A.E. and Zoorob H.H. Recent synthetic aspects on the chemistry of aminocoumarins. Chem. Intermediat. 43: 5943-5983 (2017).
- Meng T., Zou Y., Khorev O., Jin Y., Zhou H., Zhang Y., Hu D., Ma L., Wang X. and Shen J. Simple and Efficient Copper (I)-Catalyzed Access to Three Versatile Aminocoumari-Based Scaffolds using Isocyanoacetate. Synth. Catal. 353: 918-924 (2011).
- Linch F.W. Chem. Soc. Trans. 101: 1759-1765 (1912).
- Messaoudi S., Brion J.D. and Alami M. An Expeditious Copper-Catalyzed Access to 3-Aminoquinolinones, 3-Aminocoumarins and Anilines using Sodium Azide. Synth. Catal. 352: 1677-1687 (2010).
- Wan X. and Joullie M.M. Enantioselective total syntheses of trichodermamides A and B. Am. Chem. Soc. 130: 17236-17237 (2008).
|
|
- Abdshahzadeh H., Golshani M., Nadri H., Saberi Kia I., Abdolahi Z., Forootanfar H., Ameri A., Tüylü Küçükkılınç T., Ayazgok B., Jalili-Baleh L., Sadat Ebrahimi S.E., Moghimi S., Haririan I., Khoobi M. and Foroumadi A. 3-Aryl Coumarin Derivatives Bearing Aminoalkoxy Moiety as Multi-Target-Directed Ligands against Alzheimer's Disease. Biodivers. 16: e1800436 (2019).
- Khan M.A. and Gemal A.L. Synthesis of 5H[1]benzopyrano[3,4-b]pyridine-5-one and its derivatives. Heterocycl. Chem. 14: 1009-1012 (1977)
- Firoozpour L., Yahyavi H., Ejtemaei R., Moghimi S. and Foroumadi A. A one-pot, three-component, solvent-free synthesis of novel 6h-chromeno[3’,4’:5,6]pyrido[2,3-d]pyrimidine-triones under microwave irradiation. Chem. Res. 42: 604-607 (2018).
- Nikookar H., Moghimi S., Sayahi M.H., Mahdavi M., Ranjbar P.R. Firoozpour L. and Foroumadi A. A Convenient Method for the Synthesis of Chromeno[4,3-b]pyridines Via Three-component Reaction. Chem. High Throughput Screen. 21: 344-348 (2018).
- Firoozpour L., Nikookar H., Moghimi S., Mahdavi M., Asadipour A. and Ranjbar P.R. An efficient approach to the synthesis of coumarin-fused dihydropyridinones. Commun. 23: 305-308 (2017).
- Yahya-Meymandi A., Nikookar H., Moghimi S., Mahdavi M., Firoozpour, L., Asadipour A., Ranjbar P.R. and Foroumadi A. An efficient four-component reaction for the synthesis of chromeno[4,3-b]quinolone. Iran. Chem. Soc. 14: 771-775 (2016).
- Akbarzadeh T., Rafinejad A., Fallah-Tafti A., Tiwari R., Nasrolahi Shirazi A., Mandal D., Parang K. and Foroumadi A. Synthesis and Evaluation of Ethyl 2, 4-dioxo-4-arylbutanoate Derivatives as Src Kinase Inhibitors. Sci. I. R. Iran. 26: 321-325 (2015).
- Das D.K., Sarkar S., Khan M., Belal M. and Khan A.T. A mild and efficient method for large scale synthesis of 3-aminocoumarins and its further application for the preparation of 4-bromo-3-aminocoumarins. Tetrahedron Lett. 55: 4869-4874 (2014).
)