Penggunaan Iodin dalam Sintesis Dihidropirimidinon Melalui Reaksi Biginelli

Ilfahmi, Yan Alamanda (2023) Penggunaan Iodin dalam Sintesis Dihidropirimidinon Melalui Reaksi Biginelli. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa-senyawa berkerangka dihidropirimidinon diketahui berperan penting dalam pengembangan bidang kimia organik dan medisinal karena menunjukkan serangkaian aktivitas biologis yang luas seperti antikanker, antitumor, antidiabetes, antiinflamator, antibakteri, dan antimalaria. Dihidropirimidinon dapat disiapkan melalui reaksi reaksi Biginelli yang melibatkan kondensasi antara aldehida, urea/tiourea, dan β-keto ester dengan katalis asam Lewis. Dalam penelitian ini senyawa 1,2,3,4-tetrahidropirimidina 4a-4j telah diperoleh melalui reaksi antara aldehida aromatik tersubstitusi 1a-1e, urea 2a atau tiourea 2b, dan etil aseoasetat 3 dengan tiga metode. Metode A melibatkan penggunaan katalis HCl dan refluks dalam pelarut etanol. Metode B dilakukan dengan katalis iodin dan refluks dalam pelarut etanol dan metode C dijalankan dengan katalis iodin tetapi dengan penggerusan dan tanpa pelarut. Metode A, B, C yang telah dilakukan menghasilkan senyawa 4a-aj dengan persen yield bervariasi dimana metode A memberikan produk 4a-aj dengan persen yield lebih tinggi dari metode B dan metode C. Identifikasi struktur senyawa hasil sintesis yang dilakukan dengan spektrometer NMR (1H dan 13C), spektrometer FTIR, dan spektrometer massa menyatakan bahwa senyawa 4a-aj telah berhasil diperoleh.
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Dihydropyrimidinone compounds are known to play an important role in the development of organic and medicinal chemistry because they exhibit a wide range of biological activities such as anticancer, antitumor, antidiabetic, anti-inflammatory, antibacterial and antimalarial. Dihydropyrimidinone can be prepared by the Biginelli reaction which involves condensation between aldehydes, urea/thiourea, and β-keto esters with a Lewis acid catalyst. In this study, the compounds 1,2,3,4-tetrahydropyrimidine 4a-4j were obtained by the reaction between substituted aromatic aldehydes 1a-1e, urea 2a or thiourea 2b, and ethyl aceeoacetate 3 using three methods. Method A involves using HCl catalyst and refluxing in ethanol solvent. Method B was carried out with iodine catalyst and refluxed in ethanol solvent and method C was carried out with iodine catalyst but with grinding and without solvent. Methods A, B, C that have been carried out produce 4a-aj compounds with varying yield percents where method A gives 4a-4j products with higher yield percents than methods B and method C. Identification of the structure of the synthesized compound was carried out using NMR spectrometers (1H and 13C), FTIR spectrometer, and mass spectrometer stated that the 4a-aj compound had been successfully obtained.

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	dihydropyrimidinone, Biginelli reaction, iodine, dihidropirimidinon, reaksi Biginelli, Iodin
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Yan Alamanda Ilfahmi
Date Deposited:	11 Sep 2023 01:40
Last Modified:	11 Sep 2023 01:40
URI:	http://repository.its.ac.id/id/eprint/103931

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