An Efficient Synthesis of Novel Type Chalcones Containing 8-hydroxyquinoline Under Green Conditions

Year 2018, , 321 - 327, 31.08.2018

Tayfun Arslan

https://doi.org/10.18185/erzifbed.422796

Cited By: 1

Abstract

In
this study, new type of chalcones containing
8-hydroxyquinoline as
an alternative to natural and synthetic chalcones have synthesized for the
first time using microwave irradiation with environmentally benign approach.
Firstly, (E)-1-(4-((8-hydroxyquinolin-5-yl)diazenyl)phenyl)ethanone (3) were synthesized by diazotization of
p-aminoacetophenone. Secondly, most important step of synthesis included the
Claisen-Schmidt condensation of chalcones using the microwave method. The
structures of all compounds were characterized by means of FT-IR, NMR and
elemental analysis.

Keywords

Azo coupling, Chalcone, Diazotization, 8-Hydroxyquinoline

An Efficient Synthesis of Novel Type Chalcones Containing 8-hydroxyquinoline Under Green Conditions

Abstract

Bu çalışmada, çevreci bir yaklaşımla mikrodalga ışıması kullanılarak
doğal ve sentetik kalkonlara alternatif olarak 8-hidroksikinolin içeren yeni
tip kalkonlar ilk kez sentezlendi. İlk olarak, (E)-1-(4-((8-hidroksikinolin-5-yl)diazenil)fenil)ethanon
(3) p-aminoasetofenonun
diazotizasyonu tarafından sentezlendi. İkincil olarak sentezin en önemli
adımını, mikrodalga yöntemi kullanılarak kalkonların Claisen-Schmidt kondenzasyonunu
içermektedir. Tüm bileşiklerin yapıları FT-IR, NMR ve elemental analiz
yöntemleriyle karakterize edildi.

Keywords

Azo kenetlenme, Diazotizasyon, Kalkon, 8-Hidroksikinolin

References

• Abdullah, M.A., Salman, A.K. 2011. Synthesis, characterization and optical properties of mono- and bis-chalcone. Material Letters, 65, 1749-1752.
• Arslan,T., Celik, G., Celik, S., Senturk, H., Yaylı, N., Ekinci, D. 2016. Synthesis and Biological Evaluation of Novel Bischalcone Derivatives as Carbonic Anhydrase Inhibitors. Archiv der Pharmazie, 349, 741-748.
• Furman, C., Lebeau, J., Fruchart, J.C., Bernier, J.L., Duriez, P., Cotelle, N., and Teissier, E. 2001. Di-tert-Butylhydroxylated Flavonoids Protect Endothelial Cells Against OxidizedLDL-Induced Cytotoxicity. Journal of Biochemical and Molecular Toxicology, 15, 270-278.
• Ginni, S., Karnawat, R., Sharma, I.K., Verma, P.S. 2011. Synthesıs, Characterısatıon and Antımıcrobıal Screenıng of Some Azo Compounds. International Journal of Applied Biology and Pharmaceutical Technology, 2, 332-338.
• Hsieh, C.T., Hsieh, T.J., El-Shazly, M., Chuang, D.W., Tsai, Y.H., Yen, C.T., Wu, S.F., Wu, Y.C., Chang, F.R. 2012. Synthesis of chalcone derivatives as potential anti-diabetic agents. Bioorganic and Medicinal Chemistry Letters, 22, 3912-3915.
• Hua, Y.Z., Han, X.W., Yang, X.C., Song, X., M. Wang, C., and Chang, J.B. 2014. Enantioselective Friedel−Crafts Alkylation of Pyrrole with Chalcones Catalyzed by a Dinuclear Zinc Catalyst. Journal of Organic Chemistry, 79, 11690-11699.
• Hunger, K. 2003. Industrial Dyes: Chemistry, Properties, Applications. Wiley-VCH, Weinheim, 1-653.
• Kazuhiro, S., Yoh-ichi, M., Kana, M., Chiaki, K., Takanao, M. 2011. Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei. Tetrahedron, 67, 5346-5359.
• Lopez, S.N., Castelli, M.V., Zacchino, S.A., Dominguez, J.N., Lobo, G., Jaime, C.C., Cortes, J.C.G., Ribas, J.C., Devia, C., Ana, M.R., Ricardo, D.E., 2001. In vitro antifungal evaluation and structure–activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall. Bioorganic and Medicinal Chemistry, 9, 1999-2013.
• Makhloufa, M.M., Radwancid, A.S., Aly, M.R.E. 2017. Synthesis, physicochemical and spectroscopic characterizations of azochalcone derivative thin films towards solar cells application. Journal of Photochemistry and Photobiology A: Chemistry, 332, 465-474.
• Mchugh, C.J., Docherty, F.T., Graham, D., Smith, W.E. 2004. Syntheses and evaluation of dyes for multiple labelling for SERRS. Analyst, 129, 69-72.
• Modzelewska, A., Pettit, C., Achanta, G., Davidson, N.E., Huang, P., and Khana, S.R. 2006. Anticancer activities of novel chalcone and bis-chalcone derivatives. Bioorganic and Medicinal Chemistry, 14, 3491-3495.
• Saylam, A., Seferoğlu, Z., Ertan, N. 2014. “Azo-8-hydroxyquinoline dyes: The synthesis, characterizations and determination of tautomeric properties of some new phenyl and heteroarylazo-8-hydroxyquinolines. Journal of Molecular Liquids, 195, 267-276.
• Song, Y.M., Ha, Y.M., Jin-Ah, K., Chung, K.W., Uehara, Y., Lee, K.J., Chun, P., Byun, Y., Chung, H.Y., Moona, H.R. 2012. Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors. Bioorganic and Medicinal Chemistry Letters, 22, 7451-7455.
• Szala, M., Nycz, J.E., Malecki, G.J., Sokolova, R, Ramesova, S., Switlicka-Olszewska, A., Strzelczyk, R., Podsiadly, R., Machura, B. 2017. Synthesis of 5-azo-8-hydroxy-2-methylquinoline dyes and relevant spectroscopic, electrochemical and computational studies. Dyes and Pigments, 142, 277-292.
• Tosun,G., Arslan, T., Iskefiyeli, Z., Küçük, M., Karaoğlu, Ş.A., Yaylı, N. 2015. Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents. Turkish Journal of Chemistry, 39, 850-866.
• Yaylı, N., Ucuncu, O., Yasar, A., Kucuk, M., Yaylı, N., Akyuz, E., and Karaoglu, S.A. 2006. Synthesis and Biological Activities of N-Alkyl Derivatives of o-, m-, and p-Nitro (E)-4-Azachalcones and Stereoselective Photochemistry in Solution, with Theoretical Calculations. Turkish Journal of Chemistry, 30, 505-514.
• Zhuang, C., Zhang W., Sheng, C., Zhang,W., Xing, C., Miao, Z. 2017. Chalcone: A Privileged Structure in Medicinal Chemistry. Chemical Reviews, 117, 7762-7810.
• Zhao, R., Tan, C., Xie, Y., Gao, C., Liu, H., Jiang, Y. 2011. One step synthesis of azo compounds from nitroaromatics and anilines. Tetrahedron Letters, 52, 3805-3809.