Abstract
In this manuscript, a new series of 1,2,4-triazole-3-ones containing imin function was synthesized from 5-(4-bromobenzyl)-4-amino-2H-1,2,4-triazol-3(4H)-one and aromatic aldehyde by using microwave irradiation technique via schiff base reaction. Firstly, ethyl imido-p-bromophenylacetate hydrochloride (2) was synthesized according to the pinner method in the literature. Then, compound 2 was reacted with ethyl carbazate to synthesized ethyl p-bromophenylacetate etoxycarbonylhydrazone (3) compound. Then, 5-(4-bromobenzyl)-4- amino-2H-1,2,4-triazol-3(4H)-one (4) was synthesized from the reaction of ethyl p-bromophenylacetate etoxycarbonylhydrazone (3) with hydrazine monohydrate. Then, it was converted to their corresponding triazole containing Schiff bases (5a-e) with the reaction of corresponding aromatic aldehydes in ethanol by using the microwave irradiation method. This microwave technique has some advantages, including rapid and uniform heating, higher product yield and purity, mild reaction conditions, low energy requirement and shorter reaction time. The chemical structures of newly synthesized triazole containing schiff bases were identified using IR, 1HNMR, and mass spectroscopy data.
References
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- Sun, N. B., Fu, J. Q., Weng, J. Q., Jin, J. Z., Tan, C. X., Liu, X. H. (2013). Microwave assisted synthesis, antifungal activity and DFT theoretical study of some novel,1,2,4-triazole derivatives containing the 1,2,3-thiadiazole moiety. Molecules, 18(1012725–12739).
Abstract
Bu çalışmada, imin grubu içeren yeni bir seri 1,2,4-triazol-3-on türevleri mikrodalga destekli sentezlenmiştir. 5- ( 4 -Bromobenzil) - 4 - amino- 2H - 1,2,4 - triazol - 3(4H) - on bileşiği ester etoksikarbonil hidrazonun hidrazin hidrat ile reaksiyonundan elde edilmiş ve daha sonra bu bileşik çeşitli aldehitler kullanılarak Schiff bazlarına dönüştürülmüştür. Yeni sentezlenen bileşiklerin yapı aydınlatılmasında IR, 1H-NMR ve kütle spektroskopisi kullanıldı.
Bu çalışmada, imin grubu içeren yeni bir seri 1,2,4-triazol-3-on türevleri mikrodalga destekli sentezlenmiştir. 5- ( 4 -Bromobenzil) - 4 - amino- 2H - 1,2,4 - triazol - 3(4H) - on bileşiği ester etoksikarbonil hidrazonun hidrazin hidrat ile reaksiyonundan elde edilmiş ve daha sonra bu bileşik çeşitli aldehitler kullanılarak Schiff bazlarına dönüştürülmüştür. Yeni sentezlenen bileşiklerin yapı aydınlatılmasında IR, 1H-NMR ve kütle spektroskopisi kullanıldı.
Keywords
References
- Bekircan, O., Baltaş, N., Menteşe, E., & Gultekin, E. (2016). Synthesis of new fluorine-containing 1,2,4-triazole-5-on derivatives with their anti-urease, anti-xanthine oxidase and antioxidant activities. Revue Roumaine de Chimie, 61, 733–746.
- El-Sayed, H. A., Moustafa, A. H., Haikal, A. E.-F. Z. (2013). Synthesis, Antiviral, and Antimicrobial Activity of 1,2,4-Triazole Thioglycoside Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 188(5), 649–662.
- Flefel, E. M., Tantawy, W. A., El-Sayed, W. A., Sayed, H. H., Fathy, N. M. (2013). Synthesis and Anticancer Activity of New Substituted Pyrazoles and Their Derived 1,2,4-Triazoles and Sugar Derivatives. Journal of Heterocyclic Chemistry, 50(2), 344–350.
- Gokce, H., Bahceli, S., Akyildirim, O., Kol, H. Y., Kol, O. G. (2013). The Syntheses, Molecular Structures, Spectroscopic Properties (IR, Micro– Raman, NMR and UV–vis) and DFT Calculations of Antioxidant 3– alkyl–4–[3–methoxy–4–(4–methylbenzoxy)benzylidenamino]–4,5–dihydro– 1H–1,2,4–triazol–5–one Molecules. In Letters in Organic Chemistry (Vol. 10, Issue 6, pp. 395–441).
- Gürsoy-Kol, Ö., Ayazoğlu, E. (2017). Antioxidant activities and acidic properties of some novel 4-[3,4-di-(4-nitrobenzoxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Arabian Journal of Chemistry, 10, S2881–S2889.
- Kahveci, B., Menteşe, E., Akkaya, E., Yilmaz, F., Doǧan, I. S., Özel, A. (2014). Synthesis of some novel 1,2,4-triazol-3-one derivatives bearing the salicyl moiety and their anticonvulsant activities. Archiv Der Pharmazie, 347(6),449-455.
- Kahveci, B., Yilmaz, F., Menteşe, E., Beriş, F. Ş. (2012). Effect of microwave irradiation on the synthesis of 1,2,4-triazol-3-one derivatives and their antimicrobial activities. Journal of Chemical Research, 36(8), 484-488.
- Kahveci, Bahittin. (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.
- Menteşe, E., Karaali, N., Yılmaz, F., Ülker, S., Kahveci, B. (2013). Microwave-Assisted Synthesis and Biological Evaluation of Some Benzimidazole Derivatives Containing a 1,2,4-Triazol Ring. Archiv Der Pharmazie, 346(7), 556–561.
- Menteşe, E., Yilmaz, F., Baltaş, N., Bekircan, O., & Kahveci, B. (2015). Synthesis and antioxidant activities of some new triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings. Journal of Enzyme Inhibition and Medicinal Chemistry, 30(3), 435–441.
- Milcent, R., Redeuilh, C. (1980). Recherche en série du triazole‐1,2,4. II‐Réactivité des amino‐4 aryl‐3 triazol‐1,2,4 ones‐5. Journal of Heterocyclic Chemistry, 17, 1691–1696.
- Özil, M., Menteşe, E., Yilmaz, F., Islamoǧlu, F., Kahveci, B. (2011). Synthesis of novel triazol compounds containing isatin as potential antibacterial and antifungal agents by microwave and conventional methods. Journal of Chemical Research, 35(5),268-271.
- Sun, N. B., Fu, J. Q., Weng, J. Q., Jin, J. Z., Tan, C. X., Liu, X. H. (2013). Microwave assisted synthesis, antifungal activity and DFT theoretical study of some novel,1,2,4-triazole derivatives containing the 1,2,3-thiadiazole moiety. Molecules, 18(1012725–12739).
Details
| Primary Language | English |
|---|---|
| Journal Section | Research Articles |
| Authors | |
| Publication Date | June 29, 2021 |
| Published in Issue | Year 2021 Volume: 2 Issue: 1 |
