Organic chemistry

SYNTHESIS, CHARACTERIZATION, HIRSHFELD AND ADMET ESTIMATION STUDIES OF NOVEL 3-(2,4,6-TRIMETHYL-PHENYLAMINO)-BUT-2-ENOATE

Author(s):

Mohamed Loughzail, Koffi Senam Etsè, Zaragoza Verez Guillermo, Rachid Touzani, Anna Moliterni, Mohamed Anouar Harrad, Abdessamad Tounsi

Field: Organic chemistry
Type: Research paper
Issue: 2024 Volume 19, no.2
Pages: 83-92

Keywords: β-enaminoester; X-ray diffraction, monoclinic space, Hirshfeld surface, ADMET-Tox.
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https://doi.org/10.19261/cjm.2024.1220

Abstract (PDF)

Supplementary Material (PDF)

Graphycal Abstract: The compound 3-(2,4,6-timethyl-phenylamino)-but-2-enoate was obtained by the condensation reaction of ethyl acetoacetate and 2,4,6-trimethyl-phenylamine. X-ray structural analysis identified the structure of the synthesized β-enaminoester, NMR spectroscopy complemented it, and the structure stabilised by intramolecular interactions. The intermolecular contacts were further analysed by the mapping of contacts descriptors d_norm, d_e, d_i, the shape-by-shape index and surface property by electrostatic potential mapped on the Hirshfeld surface (HS). Global reactivity factors such as electronegativity, chemical hardness, potential, and softness were calculated using density functional theory. The effects of the molecular environment were accessed by analysing the electrostatic potentials surface mapped over the HS and the 3D-topology of energy frameworks. As a potential bioactive molecule, the physicochemical and ADME-Tox predictions were performed suggesting that title compound could be considered a promising drug candidate.

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ZNAL2O4@ZNO AN EFFECTIVE, HETEROGENEOUS CATALYST FOR THE SYNTHESIS OF BIS-(Β-ENAMINONES) AND BIS-(Β-ENAMINOESTERS)

Author(s):

Mohamed Anouar Harrad, Adnan Semane, Mohammed Badereddine, Abdessamad Tounsi

Field: Organic chemistry
Type: Research paper
Issue: 2024 Volume 19, no.2
Pages: 74-82

Keywords: bis-(β-enaminoester), bis-(β-enaminone), free solvent condition, condensation, catalyst heterogeneous.
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https://doi.org/10.19261/cjm.2024.1199

Abstract (PDF)

Graphycal Abstract: With ZnAl₂O₄@ZnO as a catalyst, an environmentally eco-friendly and highly effective method was developed for regio-and chemo-selective bis enamination of 1,3-dicarbonyl compounds and aromatic, aliphatic primary amines. A wide variety of bis-(β-enaminones) and bis-(β-enaminoesters) can be synthesized using this highly versatile method which offers good yields.

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GREEN AND EFFICIENT SYNTHESIS OF DIHYDROPYRIMIDINONE ANALOGUES VIA HPA-CLAY CATALYZED BIGINELLI REACTION

Author(s):

Nuzhat Rehman, Ayaz Mahmood Dar, Raja Feroz Ahmad Haji, Sharief-ud-din Khan, Deepak Pareek, Saleem Farooq, Bashir Ahmad Dar

Field: Organic chemistry
Type: Research paper
Issue: 2024 Volume 19, no.1
Pages: 76-83

Keywords: multicomponent reaction, heteropolyacid, green chemistry approach, recyclable catalyst.
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https://doi.org/10.19261/cjm.2024.1135

Abstract (PDF)
Supplementary Material (PDF)
Graphical Abstract: This study presents an eco-friendly method for synthesizing 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) through the Biginelli reaction. A novel Heteropolyacid-Clay (HPA-Clay) catalyst, formed by immobilizing H5PV2W10O40 on Montmorillonite KSF clay, displays enhanced stability and catalytic efficiency. Operating under solvent-free, one-pot conditions, the process delivers DHPMs with high yields and shortened reaction times. Catalyzed by 2 mol% HPA-Clay, it adheres to green chemistry principles, emphasizing cost-efficiency, environmental sustainability, and recyclability. The catalyst consistently performs over multiple cycles, showcasing promise for advancing Biginelli reactions.

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AROMATIC METHYL KETONES IN THE SYNTHESIS OF BIOLOGICALLY ACTIVE CHALCONES

Author(s):

Serghei Pogrebnoi

Field: Organic chemistry
Type: Review
Issue: 2024 Volume 19, no.1
Pages: 9-28

Keywords: acetophenone, vinyl-1,2,4-triazole, tetrazole-pyrazoline hybrid, Claisen-Schmidt condensation, chromenol.
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https://doi.org/10.19261/cjm.2024.1139

Abstract (PDF)
Graphical Abstract: The review is dedicated to the synthesis of 1,3-diaryl-2-propen-2-ones derived from aromatic methyl ketones. The article highlights advancements in the synthesis of chalcones and hybrid compounds based on chalcones containing 1,2,4-triazole, tetrazole-pyrazoline, and chromenol moieties. The biological activity of the synthesized compounds is comprehensively discussed.

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MILD ACIDIC CHARCOAL CATALYZED SYNTHESIS OF 3,4-DIHYDROPYRIMIDIN-2(1H)-ONE/-THIONE DERIVATIVES

Author(s):

Rajendra Patil, Jagdish Chavan, Shivnath Patel, Vaishali Shinde, Anil Beldar

Field: Organic chemistry
Type: Research paper
Issue: 2022 Volume 17, no.2
Pages: 101-108

Keywords: Biginelli reaction, acetic acid, acidic charcoal, microwave irradiation.
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https://doi.org/10.19261/cjm.2022.999

Abstract (PDF)
Supplementary Material (PDF)

Graphical Abstract: A green and efficient method for the multicomponent synthesis of 3,4-dihydropyrimidin-2(1H)-ones and -thiones using acetic acid supported on activated charcoal as a mild acid catalyst in ethanol under both conventional as well as microwave irradiation conditions has been developed. The catalyst system found more efficient under microwave irradiation conditions than conventional conditions with shorter reaction times and excellent yields.

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ONE-POT SYNTHESIS OF SUBSTITUTED BENZIMIDAZOLE DERIVATIVES UNDER ULTRASONIC IRRADIATION USING ZnFe2O4 REUSABLE CATALYST

Author(s):

Dhanraj Kamble, Anil Shankarwar, Yuvraj Sarnikar, Radhakrushna Tigote, Mubarak Shaikh, Pravin Chavan

Field: Organic chemistry
Type: Research paper
Issue: 2022 Volume 17, no.2
Pages: 94-100

Keywords: one pot reaction, substituted benzimidazole, ultrasound irradiation, ZnFe2O4 catalyst, biological activity.
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https://doi.org/10.19261/cjm.2022.892

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Supplementary Material (PDF)

Graphical Abstract: Herein, an efficient one-pot synthesis is described, of substituted benzimidazole derivatives (3a-j) from a condensation of various o-phenylenediamine (1a-j) aromatic aldehyde (2a-j) using ZnFe₂O₄ as a nano-catalyst under ultrasonic irradiation conditions. All forms of aldehydes with an electron releasing or electron –withdrawing substituent have a significant yield. The catalyst can easily be recovered after completion of the reaction and reused without affecting its activity. Prepared benzimidazole derivatives showed moderate to good anti-tuberculosis results.

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ONE-POT AND SOLVENT-FREE SYNTHESIS OF CARBODIIMIDE MODIFIED CHITOSAN; EXTRAORDINARY THERMALLY STABILITY

Author(s):

Silvadas Jesna Das, Mohan Sidharth, Chandroth Kalyad Simi

Field: Organic chemistry
Type: Research paper
Issue: 2022 Volume 17, no.1
Pages: 56-61

Keywords: chitosan, one-pot synthesis, carbodiimide, porous morphology, thermal stability.
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https://doi.org/10.19261/cjm.2022.895

Abstract (PDF)
Graphical Abstract: A facile, one-pot, and solvent-free synthesis was developed to obtain a thermally stable chitosan biopolymer. The bifunctional isocyanate by interaction with chitosan formed urea and urethane bonds between chitosan chains. Subsequently, the designed chemistry facilitated the formation of carbodiimide bonds between chitosan chains via dehydration of the urea bond. The modified chitosan was proved to be superior in thermal properties and could be used as a thermally stable bio-filler. This synthetic methodology is a facile route to achieve improved thermal stability in biopolymers.

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MICROWAVE-INDUCED CONVERSION OF ELECTROMAGNETIC ENERGY INTO HEAT ENERGY IN DIFFERENT SOLVENTS: SYNTHESIS OF β-LACTAMS

Author(s):

Aparna Das, Ram Naresh Yadav, Bimal Krishna Banik

Field: Organic chemistry
Type: Short communication
Issue: 2022 Volume 17, no.1
Pages: 62-66

Keywords: β-lactam, loss tangent, microwave, stereospecific, optically active.
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https://doi.org/10.19261/cjm.2021.864

Abstract (PDF)
Graphical Abstract: In this work, the stereospecific synthesis of optically active cis β-lactams under diverse microwave-induced conditions using diverse solvents was reported. The effects of low tanδ values of the solvents are found to be more crucial than solvents with high dipole moments and dielectric constants. The results indicated that for the synthesis of β-lactams solvents with low tanδ and high dipole moment and high dielectric constant are necessary. Best of the knowledge this is the first report that examined the importance of tanδ values of the solvents in β-lactams synthesis.

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FACILE AND EFFICIENT SYNTHESIS OF XANTHENE DERIVATIVES MEDIATED BY LANTHANUM(III) NITRATE HEXAHYDRATE UNDER SOLVENT FREE CONDITIONS

Author(s):

Kabeer Ahmed Shaikh and Uddhav Nivrutti Chaudhar

Field: Organic chemistry
Type: Research paper
Issue: 2020 Volume 15, no.2
Pages: 99-104

Keywords: lanthanum(III) nitrate, xanthene derivative, dimedone, β-naphthol, solvent free condition.
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DOI: https://doi.org/10.19261/cjm.2020.774

Abstract (PDF)
Graphical Abstract: The present paper shows that lanthanum(III) nitrate hexahydrate can be used as mild and environment friendly homogeneous catalyst for an efficient one-pot multi-component synthesis of biologically active 1,8-dioxo-octahydroxanthene and 14H-dibenzo[a,j]xanthene derivatives. The solvent free condensation reaction of aromatic aldehydes and dimedone or β-naphthol was carried out at 70-80ºC during 10-30 min. The advantages of this eco-friendly synthesis route are numerous, and include the use of an inexpensive catalyst, high to excellent yield, short reaction time and high catalytic activity that can make this method an interesting alternative to multi-step approaches.

Downloads: 118

COMPOUNDS REMOVED FROM THE CONDENSATION REACTION BETWEEN 2-ACETYLPYRIDINE AND 2-FORMYLPYRIDINE. SYNTHESIS, CRYSTAL STRUCTURE AND BIOLOGICAL EVALUATION

Author(s):

Roman Rusnac, Maria Botnaru, Nicanor Barba, Peter Petrenko, Yurii Chumakov, Aurelian Gulea

Field: Organic chemistry
Type: Research paper
Issue: 2020 Volume 15, no.2
Pages: 88-98

Keywords: 1,3-bis(pyridin-2-yl)prop-2-en-1-one, Claisen-Schmidt condensation, intramolecular aldol condensation, Michael addition, substituted cyclohexanol.
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DOI: https://doi.org/10.19261/cjm.2020.695

Abstract (PDF)

Graphical Abstract: The research is devoted to the study of unexpected products that formed as a result of the condensation reaction between 2-acetylpyridine and 2-formylpyridine under the Claisen-Schmidt reaction conditions. As a result, a sequence of reactions leading to the following compounds has been proposed: 1,3-bis (pyridin-2-yl) prop-2-en-1-one (3); 1,3,5-tri (pyridin-2-yl) pentane-1,5-dione (4); (2,4-dihydroxy-2,4,6-tri(pyridin-2-yl)cyclohexyl)(pyridin-2-yl)methanone (5) and (4-hydroxy-2,4,6-tri(pyridin-2-yl)cyclohexane-1,3-diyl)bis(pyridin-2-ylmethanone) (6) as well as 2-formylpyridine (1) and 2-acetylpyridine (2). The plausible mechanism of these chemical transformations has been proposed. All the obtained compounds demonstrate moderate antimicrobial, antifungal and antioxidant activity.

Downloads: 163