TY - JOUR T1 - Synthesis of novel 8-formyl-7-hydroxy-4-methylcoumarin derivatives AU - Çelik Onar, Hülya AU - Erdoğan, Didem PY - 2020 DA - February Y2 - 2019 DO - 10.16984/saufenbilder.503046 JF - Sakarya University Journal of Science JO - SAUJS PB - Sakarya University WT - DergiPark SN - 2147-835X SP - 134 EP - 139 VL - 24 IS - 1 LA - en AB - This study was initiated by7-hydroxy-4-methylcoumarin 1synthesis according to the Peckmann reaction with resorcinol andethylacetoacetate. This compound wasconverted into 8-formyl-7-hydroxy -4-methylcoumarin 2 compound by the Duffreaction. This aldehyde obtained wasreacted with 6-amino-1,4-benzodioxane and 2-amino benzamide, which have theirspecific biological activities, to synthesize the original two novel compounds.While 3 (7-Hydroxy-4-methyl-8-[(2,3-dihidro-1,4-benzodioxin-6-yl)iminomethyl]-2H-1-benzopiran-2-on)is obtained as a coumarin schiff base, ring closure was observed at 4 (2-(2’-Hydoxy-5-methylcoumarin-1-yl)-2,3-dihidro quinazoline-4(1H)-on). Ourcompounds are thought to exhibit biological activity. Their structures wereidentified by IR, 1H NMR, 13CNMR , MS analysis. KW - Schiff base KW - coumarin KW - Pechmann reaction KW - Duff reaction KW - 6-amino-1 KW - 4-benzodioxane CR - [1] H. Yale, M. Kalkstein, J. Med. Chem., vol.10, pp. 334, 1967. DOI: 10.1021/jm00315a010 CR - [2] K. Waisser, J. Gregor, H. Dostal, J. Kunes, L. Kubicova, V. Klimesova, J. Farmaco, vol.56, pp.803, 2001. DOI:10.1016/S0014-827X(01)01134-X CR - [3] D.J. Connolly, D. Cusack, T.P. Sullivan, P.J.Guiry, Tetrahedron, vol. 61, pp. 10153, 2005. DOI:10.1016/j.tet.2005.07.010 CR - [4] R.Sahu, D.S.Thakur, P.Kashyap, Int. J. Pharm. Sci. Nanotech., vol. 5(3), pp. 1757, 2012. CR - [5] K.S.S.Lamani, O.Kotresh, M.S.A.Phaniband, J.C.Kadakol, E.J.Chem., vol. 6, pp. 239, 2009. DOI: 10.1155/2009/787150 CR - [6] S. Ershad, L.A. Sagathforoush, G. Karim- nezhad, S. Kangari, Int. J. Electrochem. Sci., vol. 4, pp. 846, 2009. CR - [7] Z.H. Chohan, M. Praveen, S.K.A. Sherazi, Metal-Based Drugs, vol.5/5, pp. 267, 1998. DOI: 10.1155/MBD.1998.267 CR - [8] A.A. Jarrahpour, M. Motamedifar, K. Pakshir, N. Hadi, M. Zarei, Molecules, vol. 9(10), pp. 815, 2004. DOI: 10.3390/91000815 CR - [9] R. Drozdnak, B. Allaert, N. Ledoux, I. Dragutan, V. Dragutan, F. Verpoort, Coordination Chemistry Reviews, vol.249, pp. 3055, 2005. DOI:10.1016/j.ccr.2005.05.003 CR - [10] M. Shakir, M. Azam, S. Parveen, A.U. Khan, F. Firdaus, Spectrochim. Acta Part A: Mol.Biomol. Spectros., vol. 71/5, pp. 1851, 2009. DOI:10.1016/j.saa.2008.07.002 CR - [11] N. Raman, Y.P. Raja, A. Kulandaisamy, Proc. Indian Acad. Sci. (Chem. Sci.), vol. 113/3, pp. 183,2001. CR - [12] H. Çakmak, “1,2-Bis(P-Aminofenoksi) Etan Türevi Schiff Bazları ve Metal Komplekslerinin Antioksidan Özelliklerinin İncelenmesi”, PhD Thesis, Fırat Üniversitesi, pp. 8, 2007. CR - [13] Z.H. Chohan,, H. Perrvez, S. Kausar, C.T.Supuran, Synth React Inorg Met-Org Chem., vol. 32 (3), pp. 529, 2002. DOI: 10.1081/SIM-120003793 CR - [14] N.H. Al-Sha, Molecules, vol. 12 (5), pp. 1080, 2007. DOI: 10.3390/12051080 CR - [15] Z.L. You,. L. Zhu H, W.S. Liu, Z. Anorg. Allg. Chem., vol. 630, pp. 1617, 2004. DOI: 10.1002/ZAAC.200400125 CR - [16] B.G. Jeong, C.P. Rim, H.N. Chae, K.H. Chio, K.C. Nam, Y.K. Cho, Bull. Korean. Chem. Soc., vol. 17 (8), pp. 688, 1996. UR - https://doi.org/10.16984/saufenbilder.503046 L1 - https://dergipark.org.tr/en/download/article-file/967507 ER -