Sübstitüe 4-Metilkumarinlerin Sentezi ve Karakterizasyonu

Yıl 2015, Cilt: 4 Sayı: 1, 21 - 25, 19.02.2015

Kamiran Saraç Kamiran Saraç

https://doi.org/10.17798/beufen.03741

Cited By: 1

Öz

Bu çalışmada sübstitüe 4-metilkumarin türevleri   bileşik sentezlendi. Sübstitüe 4-metilkumarin sentezi için sübstitüe fenol ve etil asetoasetat maddelerinden çıkarak iyi bir verimle kumarin eldesini mümkün kılan pechmann yöntemi seçildi. Katalizör olarak sülfürik asit kullanıldı. Elde edilen bileşikler kristallendirme yöntemi ile saflaştırılıp yapıları IR, ¹H-NMR ve ¹³C-NMR gibi spektroskopik yöntemlerle aydınlatıldı.

 

Anahtar Kelimeler

Kumarin, Pechmann, Aroil klorür, Fenol

Kaynakça

• Kaynaklar
• Nachiket Dighe, Shashikant Pattan, Santosh Dengale, Deepak Musmade, Madhuri Shelar, Vishal Tambe1 and Mangesh B Hole. 2010. Synthetic and pharmacological profiles of coumarins, Scholars Research Library Archives of Applied Science Research, 2 , 65-71.
• Sethna M., Shah M.1945. The Chemstry of Coumarin., Chemical Reviews 36, 1-62.
• Coffey S., Rood S.1977. Chemistry of Carbon Compounds, Tetrahedron letters 21, 1197-1200
• Masoud M., Faranak NPolyvinylpolypyrrolidone-bound boron trifluoride (PVPP-BF3).2012 a mild and efficient catalyst for synthesis of 4-metyl coumarins via the Pechmann reaction, Comptes Rendus Chimie 15, 530-532.
• Bailey G.C., Boettner, F.1921. Production of coumarins from maleic and malic acids. Journal of Industrial and Engineering Chemistry. 13, 905-906.
• Perkin, W.H.1868. On the artificial production of coumarin and formation of its homologues. Journal of the Chemical Society, Transactions. 21, 53-63.
• E.Giles., M.P.Poulou., M.Karanis., A.Varagianis.2003. Analtica Chimica Acta.
• Topkaya taşkıran D., Alp S.2010. Kumarin türevlerinin sentezleri,karakterizasyonları ve sensör uygulamaları. Doktora Tezi, Dokuz Eylül Üniversitesi Fen Bilimleri Enstitüsü.
• Maria E., Riveiro albertina M., Ramiro V., Natalia G., Graciela F., Lidia P., Emilio Rubin C, Carina S., Carlos D.2008. Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells. Bioorganic & Medicinal Chemistry 16, 2665–2675.
• Inoue Y., Kondo H., Taguchi M., Jinbo Y., Sakamoto F., Tsukamoto G.J.1994. Synthesis and antibacterial activity of thiazolopyrazine-incorporated tetracyclic quinolone antibacterials. J. Med. Chem. 37, 586-592.
• Ivezic Z., Trkovnik M.2000. Synthesis of some new coumarin-quinolone carboxylic acid journal of heterocylıc chemıstry. 37, 137-141.
• Kempen I., Papapostolou D., Thierry N., Pochet L., Counerotte S., Masereel B., Foidart J.-M., Reboud-Ravaux M., Noel A., Pirotte B.2003. 3-Bromophenyl 6- acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo. British Journal of Cancer. 88, 1111-1118.
• Manolov I.D 2003. Synthesis and pharmacological investigations of some 4- hydroxycoumarin derivatives. Arch. Pharm. 336, 83p.
• Hoult J.R.S., Paya M.1996. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. General Pharmacology. 27, 713-722.
• Daryoush Z., Mahshad SerehnehD.2014.Recyclable CMK-5 supported sulfonic acid as an environmentallybenign catalyst for solvent-free one-pot construction of coumarinthrough Pechmann condensation, Journal of Molecular Catalysis A: Chemical 391 , 88–91.
• Meuly, W.C., Kirk-Othmer .1979. Encyclopedia of Chemical Technology, Wiley Interscience Publishers 7,1157-1160.
• Abdel-Mottaleb M.S.A., Antonious M.S., Abo-Aly M.M., Ismaiel L.F.M., El- Sayed, B.A., Sherief, A.M.K..1989. Photophysics and dynamics of rigidized coumarin laser dyes. Journal of Photochemistry and Photobiology, A: Chemistry. 50, 259-273.
• Mora A.,Paya,M., J.L., Alcaraz, M.J.1990.Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of nonenzymic lipid peroxidation. Biochemical Pharmacology. 40, 793-797.