EFFECT OF MICROWAVE IRADIATION ON THE SYNTHESIS OF SOME 1,3-BENZOXAZOL-2(3H)-ON HYBRID COMPOUNDS

Yıl 2024, Cilt: 23 Sayı: 45, 133 - 143, 26.06.2024

Fatih Yılmaz

https://doi.org/10.55071/ticaretfbd.1434905

Öz

In this work, the effects of microwave irradiation on synthesis of benzoxazole hybrid compounds containing coumarin and isatin, which are found in the structure of many natural compounds, were examined. The synthesis of 9 hybrid compounds obtained in the study was previously carried out by our research group using the traditional method. In this study, these 9 compounds were compared in terms of time, efficiency, purity, energy and solvent usage using both a home type and a monomode microwave device. As a result of these evaluations, it has been found that microwave synthesis requires significantly less solvent and energy and provides advantages in terms of efficiency and purity.

Anahtar Kelimeler

Microwave, Green chemistry, Coumarin, Benzoxazole, Isatin

MİKRODALGA IŞIMANIN BAZI 1,3-BENZOKSAZOL-2(3H)-ON HİBRİT BİLEŞİKLERİN SENTEZİ ÜZERİNE ETKİSİ

Öz

Bu çalışmada, birçok doğal bileşiğin yapısında bulunan kumarin ile isatin içeren benzoksazol hibrit bileşiklerin sentezi üzerine mikrodalga ışımanın etkileri incelenmiştir. Çalışmada elde edilen 9 hibrit bileşiğin sentezi daha önce çalışma grubumuz tarafından geleneksel yöntem kullanılarak gerçekleştirilmiştir. Bu çalışmada farklı olarak bu 9 bileşik, hem ev tipi hem de monomod mikrodalga cihazı kullanılarak zaman, verim, saflık derecesi, enerji ve çözücü kullanımı yönlerinden karşılaştırmalar yapılmıştır. Yapılan değerlendirmeler sonucunda, mikrodalga ışıma ile gerçekleştirilen sentezin önemli ölçüde daha az çözücü ve enerji gereksinimine ihtiyaç duyduğu, verim ve saflık derecesi yönünden de avantajlar sağladığı görülmüştür.

Anahtar Kelimeler

Mikrodalga, Yeşil kimya, Kumarin, Benzoksazol, İsatin

Kaynakça

• Baraldi, P. G., Bovero, A., Fruttarolo, F., Preti, D., Tabrizi, M. A., Pavani, M. G., & Romagnoli, R. (2004). DNA minor groove binders as potential antitumor and antimicrobial agents. In Medicinal Research Reviews, 24(4), 475–528.
• Creaven, B. S., Egan, D. A., Kavanagh, K., McCann, M., Noble, A., Thati, B., & Walsh, M. (2006). Synthesis, characterization and antimicrobial activity of a series of substituted coumarin-3-carboxylatosilver(I) complexes. Inorganica Chimica Acta, 359(12), 3976–3984.
• Danko, M., Szabo, E., & Hrdlovic, P. (2011). Synthesis and spectral characteristics of fluorescent dyes based on coumarin fluorophore and hindered amine stabilizer in solution and polymer matrices. Dyes and Pigments, 90(2), 129–138.
• Elsaman, T., Mohamed, M. S., Eltayib, E. M., Abdel-aziz, H. A., Abdalla, A. E., Munir, M. U., & Mohamed, M. A. (2022). Isatin derivatives as broad-spectrum antiviral agents: the current landscape. Medicinal Chemistry Research, 31(2), 244–273.
• Gencer, N., Sonmez, F., Demir, D., Arslan, O., & Kucukislamoglu, M. (2014). Synthesis, Structure-Activity Relationships and Biological Activity of New Isatin Derivatives as Tyrosinase Inhibitors. Current Topics in Medicinal Chemistry, 14 (12), 1450-1462.
• Güner, A., Bektaş, H. &Menteşe, E. (2022). Novel Coumarin Derivatives Containing a Triazole Moiety: A Study on Synthesis, Cytotoxicity, Membrane Dysfunction, Apoptosis, Cell Cycle, and Antiangiogenic Effects. Anti-cancer agents in Medicinal Chemistry, 13, 2429-2438.
• Kahveci, B. (2005). Synthesis of 4-Amino-4,5-dihydro-1H-1,2,4-triazole-5-ones and their Isatin-3-imine Derivatives. Molecules, 10(2), 376–382.
• Kahveci, B., Karaali, N., Yilmaz, F., & Menteşe, E. (2014). An efficient synthesis of some new bisbenzimidazoles via microwave technique. Turkish Journal of Chemistry, 38(3), 423–429.
• Kahveci, B., Yilmaz, F., Menteşe, E., & Ülker, S. (2015). Microwave-assisted synthesis of some new coumarin derivatives including 1,2,4-triazol-3-one and investigation of their biological activities. Chemistry of Heterocyclic Compounds, 51(5), 447–456.
• Kahveci, B., Yılmaz, F., Menteşe, E., & Ülker, S. (2017). Design, Synthesis, and Biological Evaluation of Coumarin–Triazole Hybrid Molecules as Potential Antitumor and Pancreatic Lipase Agents. Archiv Der Pharmazie, 350(8), 1–9.
• Kakkar, S., Kumar, S., Narasimhan, B., Lim, S. M., Ramasamy, K., Mani, V., & Shah, S. A. A. (2018). Design, synthesis and biological potential of heterocyclic benzoxazole scaffolds as promising antimicrobial and anticancer agents. Chemistry Central Journal, 12(1), 1–12.
• Kappe, C. O. (2004). Controlled Microwave Heating in Modern Organic Synthesis. Angewandte Chemie International Edition, 43(46), 6250–6284.
• Kaur, A., Pathak, D. P., Sharma, V., & Wakode, S. (2018). Synthesis, biological evaluation and docking study of a new series of di-substituted benzoxazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents. Bioorganic & Medicinal Chemistry, 26(4), 891–902.
• Menteşe, E., Çalışkan, N., Bilgin Sökmen, B., & Akyüz, G. (2024). Synthesis and Biological Evaluation of Coumarin-Amino Acid-Benzotriazole Conjugates. Russian Journal of Bioorganic Chemistry, 50, 191-200.
• Nath, R., Pathania, S., Grover, G., & Akhtar, M. J. (2020). Isatin containing heterocycles for different biological activities: Analysis of structure activity relationship. Journal of Molecular Structure, 1222, 1-58.
• Prusty, J. S., & Kumar, A. (2020). Coumarins: antifungal effectiveness and future therapeutic scope. Molecular Diversity, 24(4), 1367–1383.
• Raju, R., Chidambaram, K., Chandrasekaran, B., Bayan, M. F., Kumar Maity, T., Alkahtani, A. M., & Chandramoorthy, H. C. (2023). Synthesis, pharmacological evaluation, and molecular modeling studies of novel isatin hybrids as potential anticancer agents. Journal of Saudi Chemical Society, 27(2), 101598.
• Safakish, M., Hajimahdi, Z., Zabihollahi, R., Aghasadeghi, M. R., Vahabpour, R., & Zarghi, A. (2017). Design, synthesis, and docking studies of new 2-benzoxazolinone derivatives as anti-HIV-1 agents. Medicinal Chemistry Research, 26(11), 2718–2726.
• Shults, E. E., Bondarenko, S. P., Shakirov, M. M., Bagryanskaya, I. Y., & Tolstikov, G. A. (2010). Synthesis of 7-(furan-2-yl)-7,8,10,10a-tetrahydro-6H-benzo[c]-chromen-6,9(6aH)-diones. Russian Journal of Organic Chemistry, 46(11), 1709–1718.
• Yilmaz, F. & Faiz, Ö. (2018). Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. Turkish Journal of Chemical Society Sectian A., 5(2),551-568.
• Yilmaz, F., Menteşe, E., & Sökmen, B. B. (2020). Synthesis and biological evaluation of some 1,3-benzoxazol-2(3H)-one hybrid molecules as potential antioxidant and urease inhibitors. Journal of Heterocyclic Chemistry, 58(1), 260–269.
• Yılmaz, F., Menteşe, E., & Baltaş, N. (2019). Synthesis and Biological Evaluation of Some Succinimide Hybrid Molecules. Russian Journal of Bioorganic Chemistry, 45(6), 575–584.