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All Journal Jurnal Kimia Riset al Kimiya : Jurnal Ilmu Kimia dan Terapan
Ilfahmi, Yan Alamanda
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Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry

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DIFFERENT ROUTES FOR THE SYNTHESIS OF BENZALDEHYDE-BASED DIHYDROPYIMIDINONES VIA BIGINELLI REACTION Ilfahmi, Yan Alamanda; Fadlan, Arif
Jurnal Kimia Riset Vol. 8 No. 2 (2023): December
Publisher : Universitas Airlangga, Campus C Mulyorejo, Surabaya, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20473/jkr.v8i2.45209

Abstract

Multicomponent reactions involving three or more reactants are commonly used to prepare dihydropyrimidinone with various bioactivities. This study reports the different routes for the synthesis of benzaldehyde-based dihydropyrimidinone via the Biginelli reaction and investigates the yield of the obtained products. The synthesis was performed via routes A, B, C, D, and E based on the formation of iminium, enamine, and Knoevenagel intermediates between urea, benzaldehyde, and ethyl acetoacetate. Route A, through a one-pot reaction via iminium, produced dihydropyrimidinone with a yield of 58%. The product from route B via iminium was obtained in 62% yield. Route C and D occurred via enamine at room temperature, and reflux gave the product 31% and 40% yield, respectively. Route E involving Knoevenagel intermediate provided the product in a 38% yield. 1H NMR, FTIR, and MS spectroscopic techniques were used for structure elucidation.
Solvent-Free Synthesis of Dihydropyrimidinone by Using Molecular Iodine as Catalyst Fadlan, Arif; Pratama, Landaeta Yolga; Ilfahmi, Yan Alamanda
al Kimiya: Jurnal Ilmu Kimia dan Terapan Vol. 12 No. 1 (2025): June 2025
Publisher : Department of Chemistry, Faculty of Science and Technology, UIN Sunan Gunung Djati Bandung

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15575/ak.v12i1.42254

Abstract

Dihydropyrimidinone with diverse pharmacological activities can be obtained through the multicomponent of Biginelli reactions by heating aldehyde, ethyl acetoacetate and urea/thiourea in ethanol with the addition of hydrochloric acid. However, this reaction is toxic and shows several drawbacks. Further development for Biginelli reaction was conducted by using heterogeneous catalyst, green solvents, and sustainable heating such as microwave or ultrasound. But various obstacles are also found from these strategies. There are still chances to study the Biginelli reaction by using relatively simpler methods and the readily available and environmentally friendly chemicals. Iodine is a mild Lewis acid, easily available at an affordable price, non-toxic, and environmentally friendly. Iodine has been used in various reactions and organic transformations with high efficiency and selectivity. This report aims to study the solventless synthesis of ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate 4 by using molecular iodine. The reaction was studied by mixing benzaldehyde 1 as aromatic aldehyde, urea 2, and β-keto ester in the form of ethyl acetoacetate 3 with and without the addition of ethanol as solvent. The compound 4 (45% yield) was yielded from a solvent-free reaction whereas the use of ethanol gave the product 4 in 50%yield. The IR, NMR spectra, and HRMS analysis were used for the establishment of the structure of product 4. These finding give new perspective in the preparation of dihydropyrimidinone(s).
Co-Authors Fadlan, Arif Pratama, Landaeta Yolga