Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis

Zheng, Xunan; Ma, Zhengning; Zhang, Dawei

doi:10.3390/ph13030037

Cited by 99 publications

(48 citation statements)

References 58 publications

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“…Based on our previous research, we have published two reviews about the van Leusen reaction for the preparation of pyrrole-and imidazole-based molecules [41,42]. Therefore, this review, which covers the literature from 1972, will summarize the recent advances of the synthesis of oxazole-based molecules utilizing the van Leusen oxazole synthesis as an important part of van Leusen reaction, which is the [3+2] cycloaddition reaction based on TosMICs.…”

Section: Scheme 1 General Van Leusen Synthesis Base On Tosylmethylismentioning

confidence: 99%

Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

2020

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Oxazole compounds, including one nitrogen atom and one oxygen atom in a five-membered heterocyclic ring, are present in various biological activities. Due to binding with a widespread spectrum of receptors and enzymes easily in biological systems through various non-covalent interactions, oxazole-based molecules are becoming a kind of significant heterocyclic nucleus, which have received attention from researchers globally, leading them to synthesize diverse oxazole derivatives. The van Leusen reaction, based on tosylmethylisocyanides (TosMICs), is one of the most appropriate strategies to prepare oxazole-based medicinal compounds. In this review, we summarize the recent advances of the synthesis of oxazole-containing molecules utilizing the van Leusen oxazole synthesis from 1972, aiming to look for potential oxazole-based medicinal compounds, which are valuable information for drug discovery and synthesis.

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Section: Scheme 1 General Van Leusen Synthesis Base On Tosylmethylismentioning

confidence: 99%

Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

2020

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“…The simplicity of the synthesis has made this method very popular as convenient protocol for the preparation of imidazole‐based molecules. Current advances of its application are described in recent review, [ 46 ] so we exclude these methods from our work.…”

Section: [3+2]‐cycloaddition Of Activated Methylene Isocyanidesmentioning

confidence: 99%

Recent Advances in the Chemistry of Isocyanides with Activated Methylene Group

et al. 2020

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“…metronidazole, nimorazole, ciproxifan). 9,10 Additionally, imidazoles have also been utilized in various separation processes due to their ability to bind CO 2 in the bicarbonate (i.e. HCO 3…”

Section: Introductionmentioning

confidence: 99%

Scalable, safer and greener syntheses of vinylimidazoles via reactive distillation of hydroxyethylimidazole intermediates

Alshaikh

O’Harra

Liu

et al. 2021

Polymer International

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1-Vinylimidazole has been extensively utilized by the polymer science community, due to its high reactivity for free radical polymerization and the variety of uses for both neutral polyvinylimidazole and cationic polyvinylimidazolium forms. While much rarer, 4-vinylimidazoles and 2-vinylimidazoles are less synthetically accessible. In comparison to conventional methods for the synthesis of vinylimidazole derivatives from energy-intensive reaction conditions utilizing hazardous, gaseous precursors, herein we demonstrate a simple and versatile two-step method applied to the synthesis of seven 1-vinylimidazoles with different substituents as well as an initial demonstration of a facile method to synthesize the rare compound 1-methyl-2-vinylimidazole. The process relies upon the synthesis of N-hydroxyethylimidazole precursors via a ring-opening reaction from substituted imidazoles with ethylene carbonate, a 'green' substance formed from CO 2 and ethylene oxide. For the synthesis of 1-methyl-2-vinylimidazole, the hydroxyethylimidazole intermediate is conveniently formed from 1,2-dimethylimidazole and paraformaldehyde. These hydroxyethylimidazoles are subsequently dehydrated to the corresponding 1-or 2-vinylimidazole forms using a base-catalyzed reactive distillation. The optimization of process conditions is discussed, and properties of the vinylimidazole derivatives were computationally studied using density functional theory calculations. This work reveals scalable synthetic methods for previously inaccessible vinylimidazole compounds which can enable the design of new polymers.

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Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis

Cited by 99 publications

References 58 publications

Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

Recent Advances in the Chemistry of Isocyanides with Activated Methylene Group

Scalable, safer and greener syntheses of vinylimidazoles via reactive distillation of hydroxyethylimidazole intermediates

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