Synthesis of Benzylidene Bis(4-Hydroxycoumarin) Derivatives Using a Polymer Nanocomposite

Document Type : Research Article


Department of Chemistry, Lamerd Branch, Islamic Azad University, Lamerd, I.R. IRAN


In this study, polymer nanocomposites based on 2-aminophenol and Palm date have been introduced as an efficient and inexpensive catalyst and successfully used for the synthesis of benzylidene Bis(4-Hydroxycoumarin) derivatives. The polymer and nanocomposite were characterized by a Scanning Electron Microscope (SEM). Benzylidene Bis(4-Hydroxycoumarin) Derivatives have recently attracted much attention as an important class of heterocycles to their useful biological and pharmacological properties, herein we report a novel and efficient procedure for the synthesis of α,α′-benzylidenebis (4-hydroxycoumarin) derivatives based on the reaction of 4-hydroxycoumarin and aromatic aldehydes using polymer nanocomposites based on 2-aminophenol and Palm date as a solid heterogeneous catalyst in excellent yields (84-99%) and very short reaction time (2-5 min) in aqueous media (50%) have been described.


Main Subjects

[1] Astruc D., "Nanoparticles and Catalysis". WILEY-VCH, (2008).
[2] Prey V., Kerres B., Berbalk H., Zur Kenntnis der Thiolactone, Monatsh. Chem., 91(5): 774-793 (1960).
[3] Chilpa R.R., Muniz E.E., Avhla E., Abe V.F., Kinjo J., Ortega S.H., Trypanocidal Constituents in Plants. 7. Mammea-Type Coumarins, Mem. Inst. Oswaldo. Cruz., 103(5): 431-436 (2008).
[4] Rajitha B., Kumar V.N., Someshwar P., Madhav J.V., Reddy P.N., Reddy Y.T., Dipyridine Copper Chloride Catalyzed Coumarin Synthesis via Pechmann Condensation under Conventional Heating and Microwave Irradiation, ARKIVOC., 12: 23-27 (2006).
[5] Sharghi H., Jokar M., Al2O3/MeSO3H (AMA) as a Novel Heterogeneous System for Synthesis of Coumarins under Mild Conditions, Heterocycles., 71(12): 2721-2733 (2007).
[6] Stanchev S., Hadjimitova V., Traykov T., Boyanov T., Manolov I., Investigation of the Antioxidant Properties of Some New 4-Hydroxycoumarin Derivatives, Eur. J. Med. Chem., 44(7): 3077-3082 (2009).
[7] Palmisano G., Tibiletti F., Penoni A., Colombo F., Tollari S., Garella D., Tagliapietra S., Cravotto G., Ultrasound-enhanced One-Pot Synthesis of 3-(Het)arylmethyl-4-hydroxycoumarins in Water, Ultrasonics Sonochemistry., 18(2): 652-660 (2011).
[8] Manolov I., Maichle-Moessmer C., Danchev N., Synthesis, Structure, Toxicological And Pharmacological Investigations of 4-Hydroxycoumarin Derivatives, Eur. J. Med. Chem., 41(7): 882-890 (2006).
[9] Ammar H., Abid S., Fery-Forgues S., Synthesis And Spectroscopic Study of New Biscoumarin Dyes Based on 7-(4-Methylcoumarinyl) Diesters, Dyes and Pigments., 78(1): 1-7 (2008).
[11] Khan Kh. M., Iqbal S., Lodhi M.A., Maharvi Gh.M., Ullah Z., Choudhary M.I., Rahman A.U., Perveen Sh., Biscoumarin: New Class of Urease Inhibitors; Economical Synthesis and Activity Bioorg, Med. Chem, 12(8): 1963-1968 (2004).
[12] Tabatabaeian Kh., Heidari H., Khorshidi A.R., Mamaghani M., Mahmoodi N.O., Synthesis of Biscoumarin Derivatives by the Reaction of Aldehydes and 4-Hydroxycoumarin Using Ruthenium(III) Chloride Hydrate as a Versatile Homogeneous Catalyst, J. Serb. Chem. Soc., 77(4): 407-413 (2012).
[19] Karimi-Jaberi Z., Nazarifar M.R., Efficient Catalysts for the Rapid Synthesis of Benzylidene Bis(4-Hydroxycoumarin) Derivatives in Aqueous Media, Eur. Chem. Bull., 3(6): 512-514 (2014).