Sains Malaysiana 50(4)(2021): 1007-1016

http://doi.org/10.17576/jsm-2021-5004-11

 

Kaedah Gelombang Mikro; Alternatif Sintesis Sebatian Heterosiklik Konvensional

(Microwave Technique; Alternative for Synthesis Conventional Heterocyclic Compounds)

 

AZWAN MAT LAZIM1*, ATISYA ROHADI1, SITI AISHAH HASBULLAH1, MAZLAN MOHAMAD2 & A.L. ZUL ARIFF2

 

1Jabatan Kimia, Fakulti Sains dan Teknologi, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

 

2Universiti Malaysia Kelantan, 17600 UMK Jeli, Kelantan Darul Naim, Malaysia

 

Received: 12 February 2020/Accepted: 29 September 2020

 

ABSTRAK

Gelombang mikro ialah gelombang elektromagnetik yang mempunyai kemampuan untuk proses pemanasan dalam menjalankan tindak balas kimia khususnya dalam sintesis sebatian heterosiklik. Penggunaan kaedah gelombang ini adalah salah satu alternatif untuk memperbaiki atau meningkatkan tahap kecekapan suatu tindak balas dengan mengurangkan masa tindak balas malah meningkatkan peratusan hasil yang diperoleh.

 

Kata kunci: Gelang; gelombang; heterosiklik; mikro; sintesis

 

ABSTRACT

Microwave is an electromagnetic wave that has heating process ability to carry out chemical reactions especially in synthesizing heterocyclic compounds. This technique was used as an alternative to improve or increased a reaction efficiency by reducing reaction time and also raised the yields.

 

Keywords: Heterocyclic; micro; ring; synthesis; wave

 

REFERENCES

Achelle, S., Baudequin, C. & Plé, N. 2013. Luminescent materials incorporating pyrazine or quinoxaline moieties. Dyes and Pigments 98(3): 575-600.

Ajani, O.O., Obafemi, C.A., Ikpo, C.O., Ajanaku, K.O., Ogunniran, K.O. & James, O.O. 2009. Comparative study of microwave assisted and conventional synthesis of novel quinoxalinone-3-hydrazone derivatives and its spectroscopic properties. International Journal of Physical Sciences 4(4): 156-164.

Amin, K.M., Taha, A.M., George, R.F., Mohamed, N.M. & Elsenduny, F.F. 2018. Synthesis, antitumor activity evaluation and DNA-binding study of coumarin-based agents. Archiv Der Pharmazie 351(1): 1700199.

Barachevsky, V.A., Strokach, Y.P., Puankov, Y.A., Kobeleva, O.I., Valova, T.M., Levchenko, K.S. & Yaroshenko, V.N. 2009. Light-sensitive heterocyclic compounds for information nanotechnologies. ARKIVOC 5: 70-95.

Besson, T. &Thiéry, V. 2006. Microwave-assisted aynthesis of sulfur and nitrogen-containing heterocycles. Topics in Heterocyclic Chemistry 1: 59-78.

Chaubey, A. & Pandeya, S.N. 2011. Pyridine" a versatile nucleuse in pharmaceutical field. Asian Journal of Pharmaceutical and Clinical Research 4(4): 5-8.

Chauhan, M. & Kumar, R. 2015. A comprehensive review on bioactive fused heterocycles as purine-utilizing enzymes inhibitors. Medicinal Chemistry Research 24(6): 2259-2282.

Chhajed, S.S., Upasani, C.D., Bastikar, V.A. & Mahajan, N.P. 2010. Synthesis, physicochemical properties and biological evaluation of some novel 5-[2-methyl/(un) substituted phenylethylidene amino] quinolin-8-ols. Journal of Pharmacy Research 3(6): 1-3.

Cho, Y.J., Lee, S.H., Bae, J.W., Pyun, H. & Yoon, C.M. 2000. Fisher’s base as a protecting group: Protection and deprotection of 2-hydroxybenzaldehydes. Tetrahedron Letters 41(20): 3915-3917.

Danks, T.N. 1999. Microwave assisted synthesis of pyrroles. Tetrahedron Letter 40(20): 3957-3960.

De la Hoz, A. & Loupy, A. 2012. Microwaves in Organic Synthesis. 3rd ed. Weinheim, Germany: Wiley-VCH.

Dragutan, I., Dragutan, V., Delaude, L. & Demonceau, A. 2005. N-Heterocyclic carbenes as highly efficient ancillary ligands in homogeneous and immobilized metathesis ruthenium catalytic systems. ARKIVOC 10: 206-253.

Elizalde, L.E., de los Santos, G., García, A.E., Medellı´n, D.I. & Acosta, R. 2005. Synthesis of novel photochromic 6-benzyloxo-spirobenzopyran compounds. Synthetic Communications 35(24): 3087-3097.

Fadda, A.A., Abdel-Latif, E. & El-Mekawy, R.E. 2012. Synthesis of some new arylazothiophene and arylazopyrazole derivatives as antitumor agents. Pharmacology & Pharmacy 3(2): 148-157.

Fu, P.P., Xia, Q., Lin, G. & Chou, M.W. 2004. Pyrrolizidine alkaloids-genotoxicity, metabolism enzymes, metabolic activation, and mechanisms. Drug Metabolism Reviews 36(1): 1-55.

Gilchrist, T.L. 1992. Heterocyclic Chemistry. 3rd ed. Addison Wesley Longman, London: Longman. pp. 1-372.

Glowacki, E.D., Voss, G., Leonat, L., Irimia-Vladu, M., Bauer, S. & Sariciftci, N.S. 2012. Indigo and tyrian purple - from ancient natural dyes to modern organic semiconductors. Israel Journal of Chemistry 52(6): 540-551.

Haddach, A.A., Kellemanb, A. & Deaton-Rewolinski, M.V. 2002. An efficient method for the N-debenzylation of aromatic heterocycles. Tetrahedron Letters 43(3): 399-402.

Hameda, O.A., Mehdawia, N., Tahac, A.A., Hamedb, E.M., Al-Nuria, M.A. & Hussein, A.S. 2013. Synthesis and antibacterial activity of novel curcumin derivatives containing heterocyclic moiety. Iranian Journal of Pharmaceutical Research 12(1): 47-56.

Hayes, B.L. 2004. Recent advances in microwaveassisted synthesis. Aldrichimica ACTA 37(2): 66-76.

Hitchings, G.H. 1978. Uric acid: Chemistry and synthesis. In Uric Acid edited by Hitchings, G.H. Berlin, Heidelberg: Springer. pp. 1-20.

Hu, X.L., Gao, C., Xu, Z., Liu, M.L., Feng, L.S. & Zhang, G.D. 2018. Recent development of coumarin derivaties as potential antiplasmodial and antimalarial agents. Current Topics in Medicinal Chemistry 18(2): 114-123.

Jones, R.A. 1990. Pyrroles: The Synthesis and the Physical and Chemical Aspects of the Pyrrole Ring. New York: John Wiley & Sons, Inc. pp. 1-742.

Kamil, A., Akhtar, S., Farrukh, M., Hassan, S. & Jahan, S. 2013. Antibacterial and antifungal profile of 2-(2´-pyridyl) benzimidazole derivatives. European Academic Research 1(8): 2051-2058.

Katritzky, A.R. & Singh, S.K. 2003. Microwave-assisted heterocyclic synthesis. ARKIVOC 13: 68-86.

Kappe, C.O. 2004. Controlled microwave heating in modern organic synthesis. Angewandte Chemie International Edition 43(46): 6250-6284.

Khan, N.R. & Rathod, V.K. 2018. Microwave assisted enzymatic synthesis of speciality esters: A mini-review. Process Biochemistry 75: 89-98.

Landertshamer, S. & Schwarzinger, C. 2011. On the oxidation of allylmelamines. Journal of Unsolved Questions 2(1): 5-8.

Lenzen, S., Tiedge, M., Jörns, A. & Munday, R.1996. Alloxan derivatives as a tool for the elucidation of the mechanism of the diabetogenic action of alloxan. In Lessons from Animal Diabetes, edited by Lenzen, S., Tiedge, M., Jörns, A. & Munday, R. Boston: Birkhäuser. pp. 113-122.

Lidstrӧm, P., Tierney, J., Wathey, B. & Westman, J. 2001. Microwave assisted organic synthesis - A review. Tetrahedron 57(2001): 9225-9283.

Mahajan, K., Swami, M. & Singh, R.V. 2009. Microwave synthesis, spectral studies, antimicrobial approach, and coordination behavior of antimony (III) and bismuth (III) compounds with benzothiazoline. Russian Journal of Coordination Chemistry 35(3): 179-185.

Mahmood, K. & Hadi, A.H.A. 1998. Kimia Heterosiklik. Kuala Lumpur: Dewan Bahasa dan Pustaka.

Mohanan, K., Kumari, B.S. & Rijulal, G. 2008. Microwave assisted synthesis, spectroscopic, thermal, and antifungal studies of some lanthanide (III) complexes with a heterocyclic bishydrazone. Journal of Rare Earths 26(1): 16-21.

Preigh, M.J., Stauffer, M.T., Lin, F. & Weber, S.G. 1996. Anodic oxidation mechanism of a spiropyran. Journal of the Chemical Society, Faraday Transactions 92(20): 3991-3996.

Quin, L.D. & Tyrell, J.A. 2010. Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals. New York: John Wiley & Sons, Inc.

Ravichandran, S. & Karthikeyan, E. 2011. Microwave synthesis - A potential tool for green chemistry. International Journal of ChemTech Research 3(1): 466-470.

Ren, J. & Tian, H. 2007. Thermally stable merocyanine form of photochromic spiropyran with aluminum ion as a reversible photo-driven sensor in aqueous solution. Sensors 7(12): 3166-3178.

Shaker, R.M., Mahmoud, A.F. & Abdel-Latif, F.F. 2005. Facile one pot microwave assisted solvent-free synthesis of novel spiro-fused pyran derivatives via the three-component condensation of ninhydrin with malononitrile and active methylene compounds. Journal of the Chinese Chemical Society 52(3): 563-567.

Sharma, K., Singh, R., Fahmi, N. & Singh, R.V. 2010. Microwave assisted synthesis, characterization and biological evaluation of palladium and platinum complexes with azomethines. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75(1): 422-427.

Silvia, T.R., Ana, V.S.L. & González, E.A.S. 1995. Novel syntheses of spiropyran photochromatic compounds using ultrasound. Synthetic Communications 25(1): 105-110.

Surati, M.A., Jauhari, S. & Desai, K.R. 2012. A brief review: Microwave assisted organic reaction. Archives of Applied Science Research 4(1): 645-661.

Tandon, R., Singh, I., Luxami, V., Tandon, N. & Paul, K. 2019. Recent advances and developments of in vitro evaluation of heterocyclic moieties on cancer cell lines. The Chemical Record 19(2-3): 362-393.

Vačková, M. & Petro, M. 1986. Some heterocyclic azo-compounds as analytical reagents. 24. 2-(2-hydroxynaphthylazo)-7-oxo-5, 5-dimethyl-4, 5, 6, 7-tetrahydrobenzothiazole as a chelate-forming extraction reagent for copper (II), zinc (II), nickel (II), and cadmium (II). Chemical Papers 40(2): 247-255.

Van der Eycken, E., De Borggraeve, W., Dallinger, D., Dehaen, W. & Kappe, C.O. 2002. High-speed microwave-promoted hetero-diels-alder reactions of 2(1H)-pyrazinones in ionic liquid doped solvents. The Journal of Organic Chemistry 67(22): 7904-7907.

Widelski, J., Luca, S.V., Skiba, A., Chinou, I., Marcourt, L., Wolfender, J.L. & Skalicka-Wozniak, K. 2018. Isolation and antimicrobial activity of coumarin derivatives from fruits of Peucedanum luxurians Tamamsch. Molecules 23(5): 1222.

Yagi, S., Maeda, K. & Nakazumi, H. 1999. Photochromic properties of cationic merocyanine dyes. Thermal stability of the spiropyran form produced by irradiation with visible light. Journal of Materials Chemistry 9(12): 2991-2997.

Yu, Z. & Zhang, H. 2004. Ethanol fermentation of acid-hydrolyzed cellulosic pyrolysate with Saccharomyces cerevisiae. Bioresource Technology 93(2): 199-204.

Zakhs, É.R., Martynova, V.M. & Éfros, L.S. 1979. Synthesis and properties of spiropyrans that are capable of reversible opening of the pyran ring. Chemistry of Heterocyclic Compounds 15(4): 351-372.

 

*Corresponding order; email: azwanlazim@ukm.edu.my

 

   

previous