2015
DOI: 10.1039/c5ra12044f
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of 2-arylbenzimidazoles under mild conditions catalyzed by a heteropolyacid-containing task-specific ionic liquid and catalyst investigation by electrospray (tandem) mass spectrometry

Abstract: A task-specific ionic liquid constituted by a Bronsted acid (1-(3-sulfopropyl)-3-methyl-imidazolium hydrogen sulfate), namely MSI, and by [PW12O40]3−, namely PW, was used for the condensation reaction in the synthesis of 2-arylbenzimidazoles.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
4
1

Citation Types

0
5
0

Year Published

2019
2019
2024
2024

Publication Types

Select...
7

Relationship

0
7

Authors

Journals

citations
Cited by 22 publications
(5 citation statements)
references
References 20 publications
0
5
0
Order By: Relevance
“…Additionally, with the reaction of N -propiolyl-benzimidazole holding the C2 phenyl group (in place of 4-methoxyphenyl), 1m was also investigated to verify the feasibility of either ipso -cyclization or ortho -cyclization. Notably, the reaction did not progress to provide either of the annulated products; instead, hydrolysis of propiolamide was observed to give 2-phenyl benzimidazole ( 6 ) …”
Section: Results and Discussionmentioning
confidence: 99%
“…Additionally, with the reaction of N -propiolyl-benzimidazole holding the C2 phenyl group (in place of 4-methoxyphenyl), 1m was also investigated to verify the feasibility of either ipso -cyclization or ortho -cyclization. Notably, the reaction did not progress to provide either of the annulated products; instead, hydrolysis of propiolamide was observed to give 2-phenyl benzimidazole ( 6 ) …”
Section: Results and Discussionmentioning
confidence: 99%
“…[27,29] On the other hand, the traditional method for synthesizing benzothiazoles and benzimidazoles, [30,31] use Brønsted and Lewis acids as catalysts in an oxidative cyclization. Furthermore, the condensation reaction of o-phenylenediamine or o-aminothiophenol with a variety of aldehydes, acid chlorides, carboxylic acids, and nitriles in the presence of a variety of catalytic systems has been developed using Sm(OTf) 3 , [32] Ceric ammonium nitrate [CAN], [33] CeO 2 -ZrO 2 , [34] VOSO 4 , [35] Zn 3 (BTC) 2 MOF, [36] K 2 S 2 O 8 , [37] Bi(NO 3 ) 3 , [38] 4-MethoxyTEMPO, [39] Fe/ionic liquid, [40] Chlorotrimethylsilane, [41] via electrosynthesis, [42] hydrotalcite, [43] and hexamethylenetetramine-bromine complex. [44] While the above-mentioned reports were successfully completed employing a variety of catalysts or reagents, these methods have some drawbacks, including the use of expensive catalysts, toxic reagents and solvents, long reaction times, the formation of side products, the use of strong oxidizing reagents, stoichiometric quantities, and the use of metal salts, all of which are harmful to the environment.…”
Section: Introductionmentioning
confidence: 99%
“…On the other hand, the traditional method for synthesizing benzothiazoles and benzimidazoles, [30,31] use Brønsted and Lewis acids as catalysts in an oxidative cyclization. Furthermore, the condensation reaction of o‐phenylenediamine or o‐aminothiophenol with a variety of aldehydes, acid chlorides, carboxylic acids, and nitriles in the presence of a variety of catalytic systems has been developed using Sm(OTf) 3 , [32] Ceric ammonium nitrate [CAN], [33] CeO 2 ‐ZrO 2 , [34] VOSO 4 , [35] Zn 3 (BTC) 2 MOF, [36] K 2 S 2 O 8 , [37] Bi(NO 3 ) 3 , [38] 4‐MethoxyTEMPO, [39] Fe/ionic liquid, [40] Chlorotrimethylsilane, [41] via electrosynthesis, [42] hydrotalcite, [43] and hexamethylenetetramine‐bromine complex [44] …”
Section: Introductionmentioning
confidence: 99%
“…4447 In particular, some ILs as catalysts exhibit good performances in the oxidative condensation of aldehydes or benzylamines with o -phenylenediamine to give benzimidazoles. 4649 More particularly, some Brönsted acid ILs as catalysts performed well in condensation reactions to afford benzimidazoles and bis(arylidene)cycloalkanones. 50,51…”
Section: Introductionmentioning
confidence: 99%