Sintesis Senyawa Bis-pirazol Melalui Reaksi Multikomponen Satu Wadah Menggunakan Iodin Dalam Kondisi Bebas Pelarut

Fuadi, Raihana Putri Nariswari (2026) Sintesis Senyawa Bis-pirazol Melalui Reaksi Multikomponen Satu Wadah Menggunakan Iodin Dalam Kondisi Bebas Pelarut. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa bis-pirazol menunjukkan aktivitas antimikroba, antiinflamasi, antioksidan, dan mampu menghambat proliferasi sel kanker. Senyawa bis-pirazol juga diaplikasikan dalam kimia material, katalisis organik, dan sensor molekuler. Metode sintesis senyawa bis-pirazol dari reaksi siklokondensasi antara hidrazin atau turunannya dengan senyawa 1,3-diketon atau β-ketoester melalui siklisasi yang diikuti dengan substitusi oleh aldehida aromatik terus dikembangkan. Namun, berbagai metode yang dikembangkan masih menunjukkan kelemahan yang serius. Penelitian ini melaporkan sintesis senyawa bis-pirazol melalui reaksi multikomponen satu wadah menggunakan iodin dalam kondisi bebas pelarut. Sintesis senyawa bis-pirazol dilakukan antara benzaldehida 3a, vanillin 3b, dan 4-nitrobenzaldehida 3c dengan fenilhidrazin 1 dan etil asetoasetat 2 melalui pengadukan dan pemanasan pada suhu 70°C selama 30 menit. Senyawa 4,4′-(fenilmetilena)bis(3-metil-1-fenil-1H-pirazol-5-ol) (4a), 4,4′-((4-hidroksi-3-metoksifenil)metilena)bis(3-metil-1-fenil-1H-pirazol-5-ol) (4b), dan 4,4′-((4-nitrofenil)metilena)bis(3-metil-1-fenil-1H-pirazol-5-ol) (4c). Masing-masing telah diperoleh dengan yield 47, 51, dan 52%. Identifikasi struktur senyawa hasil sintesis 4a-c dilakukan dengan spektroskopi FTIR dan 1H-NMR serta analisis massa.
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Bis-pyrazole compounds exhibit antimicrobial, anti-inflammatory, and antioxidant activities and have been reported to inhibit cancer cell proliferation. Furthermore, these compounds have found applications in materials chemistry, organic catalysis, and molecular sensing. The synthesis of bis-pyrazole derivatives via cyclocondensation reactions between hydrazine or its derivatives and 1,3-diketones or β-ketoesters, followed by cyclization and subsequent substitution with aromatic aldehydes, has been extensively investigated. Nevertheless, many of the existing synthetic protocols still suffer from significant limitations. In the present study, the synthesis of bis-pyrazole compounds was carried out through a one-pot multicomponent reaction catalyzed by iodine under solvent-free conditions. Benzaldehyde (3a), vanillin (3b), and 4-nitrobenzaldehyde (3c) were reacted with phenylhydrazine (1) and ethyl acetoacetate (2) under continuous stirring and heating at 70 °C for 30 min. The target compounds, namely 4,4'-(phenylmethylene) bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) (4a), 4,4'-((4-hydroxy-3-methoxyphenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) (4b), and 4,4'-((4-nitrophenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) (4c), were obtained in yields of 47%, 51%, and 52%, respectively. The molecular structures of the synthesized compounds (4a–c) were elucidated using FTIR and 1H NMR spectroscopy as well as mass spectrometric analysis.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	bis-pirazol, iodin, reaksi multikomponen, bebas pelarut bis-pyrazole, iodine, multicomponent reaction, solvent-free conditions
Subjects:	Q Science Q Science > QD Chemistry Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Raihana Putri Nariswari Fuadi
Date Deposited:	04 Feb 2026 01:09
Last Modified:	04 Feb 2026 01:09
URI:	http://repository.its.ac.id/id/eprint/132062

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