Synthesis of bis(4-hydroxycoumarin)methanes using nano-CuO/CeO2 as recyclable catalyst

Baghernejad, Bita; Parhizgar, Saman

doi:10.26655/AJNANOMAT.2021.3.1

Document Type : Original Article

Authors

Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran

https://doi.org/10.26655/AJNANOMAT.2021.3.1

Abstract

Coumarin derivatives have been widely utilized as agrochemicals, cosmetics, and pigments, demonstrating broad spectrum biological and pharmacological activities. In this research study, we reported an efficient and environmentally benign one-pot multi–component reaction for the synthesis of bis(4-hydroxylcoumarin) methanes derivatives from the reaction of 4-hydroxycoumarin and aromatic aldehydes in the presence of a catalytic amount of nano- CuO/CeO₂. The advantages of this method are including, good yields (92-97%), short reaction times, simple work-up and reusable catalyst. The catalyst could be recycled and reused for five times without much loss in its activity. As is evident from this research study, the best efficiency for the synthesis of bis(4-hydroxylcoumarin) methanes is achieved with the nano-CuO/CeO₂ catalyst in the shortest time.

Graphical Abstract

Keywords

Main Subjects

Organic Chemistry

References

[1]. Lee B.H., Clothier M.F., Dutton F.E., Conder G.A., Johnson S.S. Bioorg. Med. Chem. Lett., 1998, 8:3317

[2]. Stahmann A., Ikawa M., Link K.P. U.S. ChemicalAbstract., 1948, 42:P603h

[3]. Hinman J.W., Hoeksema H., Caron E.L., Jackson W.G. J. Am. Chem. Soc., 1956, 78:1072

[4]. Singer L.A., Kong N.P. J. Am. Chem. Soc., 1966, 88:5213

[5]. Chand M. Archiv. Org. Inorg. Chem. Sci., 2018, 2:1

[6]. Karimi-Jaberi Z., Nazarifar M.R. Europ. Chem. Bull., 2014, 3:512

[7]. Nolan A.K., Doncaster R.J., Dunstan S.M., Scot A.K., Frenkel D., Siegel D., Ross D., Barnes J., Levy C., Leys D. J. Med. Chem., 2009, 57:7142

[8]. Mahajan D.H., Pannecouque C., De Clercq E., Chikhalia K.H. Archiv. Pharmazie., 2009, 342:281

[9]. Jurd L., Corse J., King A.D., Bayne H., Mihara K. Phytochem., 1971, 10:2965

[10]. Ojala T., Remes S., Haansuu P., Vuorela H., Hiltunen R., Haahtela K., Vuorela P. J. Ethnopharmacolo., 2000, 73:299

[11]. Chiang C.C., Hsu L.Y., Tsai H.J., Yao C.W., Chang T.C. J. Chiong. Chang. Inst. Tech., 2008, 37:15-22

[12]. Ćavar S., Kovač F., Maksimović M. Food. Chem., 2009, 117:135

[13]. Jung J.C., Park O.S. Molecules., 2009, 14:4790

[14]. Završnik D., Muratovic S., Makuc D., Plavec J., Cetina M., Nagl A., De Clercq E., Balzarini J., Mintas M. Molecul., 2011, 16:6023

[15]. O’Kennedy R., Thornes, R.D. Coumarins: Biology, applications and mode of action. John Wiley & Sons, New York. 1997

[16]. Panitsiri A., Tongkhan S., Radchatawedchakoon W., Sakee U. J. Mol. Struct., 2016, 1107:14

[17]. Xu X., Hu X., Wang J. Beilst. J. Org. Chem., 2013, 9:254

[18]. Fardood S.T., Ramazani A., Joo S.W. J. Appl. Chem. Res., 2017, 11:8

[19]. Khodaei R., Ahmady A., Omidfar K. Microchimica. Acta., 2019, 186:170

[20]. Al Banna L.S., Salem M.N., Jaleel G.A., Awwad A.M. Chem. Int., 2020, 6:137

[21]. Matin T., Gasemi N., Ghodrati K., Ramezani M. Eurasian. Chem. Commin., 2019, 1:494

[22]. Fardood S.T, Moradnia F., Moradi S., Forootan R., Yekke Zare F. Nanochem. Res., 2019, 4:140

[23]. Taghavi Farhood S., Moradnia F., Ramezani A. Micro. Nano. Lett., 2019, 14:986

[24]. Moradnia F., Mostafaei M., Afshari Z., Faramarzi V. Nanochem. Res., 2019, 4:86

[25]. Moradnia F., Fardood S.T., Ramazani A. Gupta V.K. J. Photochem. Photobiol. A: Chem., 2020, 392: 112433

[26]. Fardood S.T., Forootan R., Moradnia F., Ashrafi Z., Ramazani A. Material. Research. Exp., 2020, 7:015086

[27]. Fardood S.T., Ramazani A., Moradnia F., Ashrafi Z., Ganjkhanlu S., Yekke Zare F. Chem. Method., 2019, 3:696

[28]. Moradnia F., Ramazani A., Fardood S.T., Gouranlou F. Mat. Research. Exp., 2019, 6:075057

[29]. Perez-pastenes H., Ochoa-tapia A., Viveros T. J. Sol-Gel. Sci. Technology., 2006, 37:49

[30]. Khodaei M.M., Khosropour A.R., Moghani H. J. Org. Chem., 2006, 41:916

[31]. Harrison P.G., Ball I.K., Azelee W., Daniell W., Goldfarb D. Chem. Mater., 2000, 12:3715

[32]. Noorizadeh H., Abbasi Sh. Chem. Method., 2019, 3:583

[33]. Kargar-Dolatabadi A., Zare A. Iran. Chem. Commun., 2017, 5:252

[34]. Ramazani A., Moradnia F., Aghahosseini H. Curr. Org. Chem., 2017, 21:1612

[35]. Prasad R., Rattan G. Bull. Chem. React. Eng. Catal, 2010, 5:2010

[36]. Khadijah M., Zaydi A. Molecules, 2003, 8:54

Asian Journal of Nanoscience and Materials

Synthesis of bis(4-hydroxycoumarin)methanes using nano-CuO/CeO2 as recyclable catalyst

References

References

Volume 4, Issue 3
July 2021
Pages 178-187

Synthesis of bis(4-hydroxycoumarin)methanes using nano-CuO/CeO2 as recyclable catalyst

References

References

Volume 4, Issue 3July 2021Pages 178-187

Volume 4, Issue 3
July 2021
Pages 178-187