1632-83-3Relevant articles and documents
Palladium-Catalyzed Ligand-Free C-N Coupling Reactions: Selective Diheteroarylation of Amines with 2-Halobenzimidazoles
Sang, Wei,Gavi, Ayao Jean,Yu, Bao-Yi,Cheng, Hua,Yuan, Ye,Wu, Yuan,Lommens, Petra,Chen, Cheng,Verpoort, Francis
, p. 129 - 135 (2020)
2-Aminobenzimidazoles are widely present in a number of bioactive molecules. Generally, the preparation of these molecules could be realized by the mono-substitution of 2-halobenzimidazoles with amines. However, rare examples were reported for the di-subs
Self-Assembly of Benzimidazole-Derived Tris-NHC Ligands and AgI-Ions to Hexanuclear Organometallic Cages and Their Unusual Transmetalation Chemistry
Nishad, Rajeev C.,Rit, Arnab
, p. 594 - 599 (2021)
Multi-ligand self-assembly to attain the AgI-N-heterocyclic carbene (NHC)-built hexanuclear organometallic cages of composition [Ag6(3 a,b)4](PF6)6 from the reaction of benzimidazole-derived tris(azolium) salts [H3-3 a,b](PF6)3 with Ag2O was achieved. The molecular structures of the cages were established by X-ray diffraction studies along with NMR and MS analyses. The existence of a single assembly in solution was supported by diffusion-ordered spectroscopy (DOSY) 1H NMR spectra. Further, transmetalation reactions of these self-assembled complexes, [Ag6(3 a,b)4](PF6)6, with CuI/AuI-ions provided various coinage metal-NHC complexes having diverse molecular compositions, which included the first example of a hexanuclear CuI-dodecacarbene complex, [Cu6(3 b)4](PF6)6.
Walther reaction in the benzazoles series and preparation of their 2-deutero derivatives
Lomov,Yutilov,Smolyar
, p. 241 - 242 (2006)
Reactions of 2-hydrazino-substituted 1-methylbenzimidazole, benzothiazole, and benzoxazole with azobenzene at 160-180°C resulted in hydrazino group elimination and formation of the corresponding 2-H-benzazoles. Under similar conditions the 2-deuterohydrazinobenzazoles prepared from 2-hydrazinobenzazoles and heavy water were converted into 2-deuterobenzazoles. Pleiades Publishing, Inc. 2006.
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Inoue,Yokoo
, p. 3651 (1972)
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Alley,Shirley
, p. 1791 (1958)
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Kinetic analysis of the complete mechanochemical synthesis of a palladium(II) carbene complex
Allenbaugh, Rachel J.,Zachary, Jonathon R.,Underwood, A. Nicole,Bryson, J. Dillion,Williams, Joseph R.,Shaw, Angela
, (2020)
Benzimidazoline-2-ylidene complexes of palladium(II) were synthesized mechanochemically in a vibratory ball mill. Complete syntheses began with preparation of benzimidiazolium halides from commercially available starting materials. These “greener chemistr
Solid-phase synthesis of 1,2-benzophenazine and some fused imidazole derivatives
Zefirov,Sereda,Volkov,Tkachenko,Zyk
, p. 577 - 579 (1996)
The solid-phase synthesis of 1,2-benzophenazine and various N-methylbenzimidazoles using o-diaminoarenes is very promising and permits the synthesis of 1-methyl-4,5-[b]naphtho-1H-imidazole, which could not be obtained by the condensation of o-diaminoarenes with paraformaldehyde using the standard liquid-phase method. 1996 Plenum Publishing Corporation.
An interchangeable homogeneous ? heterogeneous catalyst system for furfural upgrading
Wang, Lu,Chen, Eugene Y.-X.
, p. 5149 - 5153 (2015)
Intercalation of benzimidazolium cations [BI]+ into the nanogalleries of Na+/montmorillonite (MMT) clay leads to generation of recyclable supported precatalysts [BI]+/MMT, which, upon treatment with a base, catalyze furfural self-condensation coupling reaction into furoin in almost constant yields of >96% over the three cycles investigated. This catalyst system combines the best features of both homogeneous and heterogeneous catalyst systems, as it performs the homogeneous molecular catalysis by the discharged N-heterocyclic carbene catalyst in solution and then recovers the catalyst through in situ heterogenization after the reaction via re-intercalation of the charged precatalyst. The [12,12BI]+/MMT catalyst system carrying two long-chain C12 dodecyl substituents on the [BI] nitrogen atoms is particularly effective for achieving both high product yield and catalyst recyclability.
The reaction of 1-ethoxycarbonyl-3-methylbenzimidazolium salts with electrogenerated and potassium superoxide
Itoh,Nagata,Okada,Ohsawa
, p. 1154 - 1156 (1994)
1-Ethoxycarbonyl-3-methylbenzimidazolium salts, which have two possible reactive sites toward superoxide, were allowed to react with KO2 and electrogenerated superoxide to give the ring-opened products and 1- methylbenzimidazoles. The former compounds were specific products for superoxide, and the product distributions were revealed to depend on the counter cation of superoxide.
ACYLATION OF BENZIMIDAZOLE BY THE REGEL-BUECHEL METHOD. 2. DEACYLATION AND DISSOCIATION OF 1-METHYL-3-ACYL-2-(1'-METHYL-2'-BENZIMIDAZOLYL)-4-BENZIMIDAZOLINES
Khristich, B. I.,Bondarenko, E. V.
, p. 284 - 287 (1987)
With excess acyl halide 1-methyl-3-acyl-2-(1'-methyl-2'-benzimidazolyl)-4-benzimidazoline is converted to an unstable 1-methyl-3-acyl-2-(1'-methyl-3-acyl-4'-benzimidazolin-2'-yl)benzimidazolium chloride, which undergoes intramolecular redox cleavage with the formation of 1,1'-dimethyl-2,2'-dibenzimidazolyl and an aldehyde and dissociates at the C-C bond that connects the benzimidazolium and benzimidazoline fragments into a carbene yield and a 1-methyl-3-acylbenzimidazolium chloride.
Using Methanol as a Formaldehyde Surrogate for Sustainable Synthesis of N-Heterocycles via Manganese-Catalyzed Dehydrogenative Cyclization
Li, Yibiao,Liu, Qiang,Shao, Zhihui,Yuan, Shanshan
supporting information, (2022/02/23)
The development of an efficient and sustainable synthetic route for formaldehyde production from renewable feedstock, especially in combination with a subsequent transformation to straightforwardly construct valuable chemicals, is highly desirable. Herein, we report a novel manganese-catalyzed dehydrogenative cyclization of methanol as a formaldehyde surrogate with a variety of dinucleophiles for facile synthesis of N-heterocycles. The in situ generated formaldehyde via catalytic methanol dehydrogenation can be selectively trapped by diverse dinucleophiles to avoid several possible side reactions. The utility of this transformation is further highlighted by its successful application to the synthesis of 13C-labeled N-heterocycles using 13CH3OH as a readily accessible 13C-isotope reagent.
Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes
Dong, Yaxi,Breit, Bernhard
supporting information, p. 6765 - 6769 (2021/09/11)
CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.
