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Keywords = chalcone spacer

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13 pages, 2306 KiB  
Article
Exploring Regio- and Stereoselectivity in [3+2] Cycloaddition: Molecular Electron Density Theory Approach for Novel Spirooxindole-Based Benzimidazole with Pyridine Spacer
by Saeed Alshahrani, Abdullah Mohammed Al-Majid, Abdullah Saleh Alamary, Mar Ríos-Gutiérrez and Assem Barakat
Crystals 2023, 13(7), 1085; https://doi.org/10.3390/cryst13071085 - 11 Jul 2023
Cited by 1 | Viewed by 1559
Abstract
A new ethylene derivative was synthesized as a precursor for the [3+2] cycloaddition (32CA) reaction to access a novel spirooxindole embodied with benzimidazole with a pyridine spacer. The chalcone derivatives 3aj is obtained with condensation of the acetyl derivative with aryl [...] Read more.
A new ethylene derivative was synthesized as a precursor for the [3+2] cycloaddition (32CA) reaction to access a novel spirooxindole embodied with benzimidazole with a pyridine spacer. The chalcone derivatives 3aj is obtained with condensation of the acetyl derivative with aryl aldehydes. The one-pot multi-component reaction of the ethylene derivative, 5-Cl-isatin, and octahydroindole-2-carboxylic acid enables the construction of a highly functionalized quaternary center spirooxindole scaffold in a high chemical yield. A study using the Molecular Electron Density Theory (MEDT) explains the complete regio- and stereoselectivity of the reaction, resulting in the exclusive formation of the ortho/endo-cycloadduct under kinetic control. The low activation Gibbs free energy is the result of the supernucleophilic character of the in situ-generated azomethine ylide and the strong electrophilic character of the ethylene derivatives. Full article
(This article belongs to the Section Organic Crystalline Materials)
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13 pages, 8349 KiB  
Article
Synthesis and In Vitro Antimicrobial Evaluation of Photoactive Multi—Block Chalcone Conjugate Phthalimide and 1,8-Naphthalimide Novolacs
by Periyan Durairaju, Chinnasamy Umarani, Govindasami Periyasami, Perumberkandigai Adikesavan Vivekanand and Mostafizur Rahaman
Polymers 2021, 13(11), 1859; https://doi.org/10.3390/polym13111859 - 3 Jun 2021
Cited by 10 | Viewed by 2763
Abstract
Herein we report new multiblock chalcone conjugate phthalimide and naphthalimide functionalized copolymers with a topologically novel architecture synthesis using nucleophilic substitution and polycondensation methodology. The structures of the synthesized novolacs were elucidated on the basis of their spectroscopic analysis including FTIR, 1H [...] Read more.
Herein we report new multiblock chalcone conjugate phthalimide and naphthalimide functionalized copolymers with a topologically novel architecture synthesis using nucleophilic substitution and polycondensation methodology. The structures of the synthesized novolacs were elucidated on the basis of their spectroscopic analysis including FTIR, 1H NMR, and 13C NMR spectroscopy. Further, the number-average and weight-average molecular weights of the novolac polymers were determined by gel permeation chromatography (GPC). We examined the solubility of the synthesized polymers in various organic solvents including CHCl3, CH3CN, THF, H2O, CH3OH, DMSO, and DMF and found they are insoluble in both methanol and water. The novolac polymers were evaluated for their photophysical properties and microbial activities. The investigation of the antimicrobial activities of these polymers reveals significant antimicrobial activity against the pathogens E. coli, S. aureus, C. albicans, and A. niger. Full article
(This article belongs to the Section Polymer Chemistry)
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