Syntheses of polyalkylated imidazoles

Evjen, Sigvart; Fiksdahl, Anne

doi:10.1080/00397911.2017.1330416

Cited by 23 publications

(34 citation statements)

References 13 publications

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“…KOH pellets were carefully ground to a fine powder using a mortar and pestle. 4,5‐Dimethylimidazole and 2,4,5‐trimethylimidazole were synthesized via the Debus–Radziszewski reaction, according to an established literature procedure 28 …”

Section: Methodsmentioning

confidence: 99%

“…4,5-Dimethylimidazole and 2,4,5-trimethylimidazole were synthesized via the Debus-Radziszewski reaction, according to an established literature procedure. 28 Synthetic methods A series of 1-vinylimidazoles with various substituents (Table 1) were synthesized in a two-step procedure. First, a series of 1-(2-hydroxyethyl)imidazole compounds (1a-g) were synthesized via reaction with EC, while 1-methyl-2-ethanolimidazole (1h) was synthesized via the reaction of 1,2-dimethylimidazole with paraformaldehyde.…”

Section: Experimental Materialsmentioning

confidence: 99%

“…Despite the accessibility and scalability of synthetic routes in the literature for the production of polyalkylated imidazole derivatives (primarily via Debus-Radziszewski imidazole synthesis), very few substituted 1-vinylimidazoles are available commercially at a reasonable cost. [28][29][30][31] Substituted 1-vinylimidazoles could be utilized to tune the properties of the polyvinylimidazole forms through controlling sterics, electronics and stability of the pendant imidazole moiety.…”

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confidence: 99%

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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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Section: Methodsmentioning

confidence: 99%

Section: Experimental Materialsmentioning

confidence: 99%

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confidence: 99%

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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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“…After assembling various enediol diacetates, these reaction modules were used to construct imidazoles with a simple nitrogen source, (NH 4 ) 2 CO 3 . [23][24][25][26][27] The effects of reaction temperature on the formation of imidazole derivatives were investigated by using 1-(4-methoxyphenyl)ethene-1,2-diyl diacetate (2b) with (NH 4 ) 2 CO 3 as the nitrogen source and methanol as the solvent ( Table 2). The results showed that a reaction temperature 64 °C gave the highest yield.…”

Section: Paper Syn Thesismentioning

confidence: 99%

Preparation of Imidazole Derivatives via Bisfunctionalization of Alkynes Catalyzed by Ruthenium Carbonyl

Ruan

Chen

et al. 2019

Synthesis

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A one-step, oxidative bisfunctionalization of alkynes to generate cis-enediol diacetates catalyzed by ruthenium carbonyl (triruthenium dodecacarbonyl) is presented. The reaction was performed using the alkyne, (diacetoxyiodo)benzene, Ru3(CO)12 as the catalyst, and toluene as the solvent at 100 °C to give the cis-enediol diacetates in up to 82% yields. This method overcomes the shortcomings of existing methods, such as tedious reaction steps, substrate limitations, and the use of toxic reagents. Furthermore, the reaction of module cis-enediol diacetates with ammonium carbonate [(NH4)2CO3] in an alcohol solvent gave imidazole derivatives in 37–84% yields, thus providing a simple and mild new method for the synthesis of imidazole compounds.

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“… 12 Undoubtedly, the further development of mild, efficient, and general MCRs for the direct assembly of a key structural motif is still highly desired. 13 …”

Section: Introductionmentioning

confidence: 99%

Bran-New Four-Molecule and Five-Molecule Cascade Reactions for One-Pot Synthesis of Pyrano[3,2-c]chromen-5-ones and Spiro[benzo[b][1,4]diazepine-2,2′-pyrano[3,2-c]chromen]-5′-ones under Catalyst- and Solvent-Free Conditions

Zhu

Zhou

et al. 2018

ACS Omega

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Herein, two versatile bran-new methods have been developed for building three new kinds of complicated-framework compounds including 2,4,4-trimethyl-2-(phenylamino)-3,4-dihydro-2H,5H-pyrano[3,2-c]chromen-5-ones, 4,4,4′,4′-tetramethyl-1,3,3′,4,4′,5-hexahydro-5′H-spiro-[benzo[b][1,4]diazepine-2,2′-pyrano[3,2-c]-chromen]-5′-ones, and 2,2,4′,4′-tetramethyl-2,3,3′,4′-tetrahydro-5H,5′H-spiro[benzo[b][1,4]-oxazepine-4,2′-pyrano[3,2-c]chromen]-5′-ones in a one-pot manner via four-molecule and five-molecule cascade reactions of commercially available 4-hydroxychromen-2-one, substituted anilines, and acetone. In consideration of these impressive features including no need of additional catalysts and solvents, moderate to good yields, excellent site-selectivity, and broad substrate/functional group tolerance, we believe that the two present protocols should have the potential for broad synthetic utility.

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Syntheses of polyalkylated imidazoles

Cited by 23 publications

References 13 publications

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

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

Preparation of Imidazole Derivatives via Bisfunctionalization of Alkynes Catalyzed by Ruthenium Carbonyl

Bran-New Four-Molecule and Five-Molecule Cascade Reactions for One-Pot Synthesis of Pyrano[3,2-c]chromen-5-ones and Spiro[benzo[b][1,4]diazepine-2,2′-pyrano[3,2-c]chromen]-5′-ones under Catalyst- and Solvent-Free Conditions

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