Synthesis of Benzimidazoles via Iron-Catalyzed Aerobic Oxidation Reaction of Imine Derivatives with o-Phenylenediamine

Yu, Jiatao; Lu, Ming

doi:10.1080/00397911.2015.1062987

Cited by 15 publications

(11 citation statements)

References 22 publications

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“…The above results led us to further investigate the generality of this reaction, and we then evaluated this hydrogen transfer/coupling methodology for the direct synthesis of aza heterocyclic derivatives from 2-nitroaniline 5 . By reaction with benzylalcohol, benzimidazole , 6a can be obtained in 28% yield when performing the reaction with 5 mol % of the Knölker complex, 10 mol % of Me 3 NO, and 1 equiv of K 3 PO 4 ·H 2 O in mesitylene at 160 °C for 24 h. Noticeably using the (1,4-dimethyl-5,7-diphenyl-3,4-dihydro-1 H -cyclopenta-[ b ]pyrazine-6(2 H )-one)iron tricarbonyl complex developed by Renaud et al as the catalyst, only 17% of 6a was obtained under the same conditions (see Table S2 for details of the optimization). Thus, 6a–c can be obtained with 64–72% yields but an additional step with DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 0.5 equiv) was required to oxidize the dihydrobenzimidazole intermediate .…”

Section: Resultsmentioning

confidence: 99%

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

Darcel

2020

J. Org. Chem.

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A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30−91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64− 72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28−96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

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Section: Resultsmentioning

confidence: 99%

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

Darcel

2020

J. Org. Chem.

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“…Yu and Lu prepared 2‐arylbenzimidazoles ( 77 ) in a unique reaction of o ‐phenylenediamine ( 4 ) with different oximes ( 75 ) and imines ( 76 ) in water and acetonitrile, respectively, catalyzed by Fe (NO 3 ) 3 .9H 2 O (5–10 mol %) at 80–100°C. The yield was 65–95% (Scheme ) .…”

Section: Oxidative Coupling Of O‐phenylenediamine Using Transition Mementioning

confidence: 99%

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

Singhal

Khanna

Panda

et al. 2019

Journal of Heterocyclic Chem

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Benzimidazole is a heterocyclic moiety of immense importance as it acts as a primary “biolinker” in diverse synthetic routes to obtain bioactive compounds. Substituted benzimidazoles are known to possess a varied range of pharmacological applications, namely, anti‐cancer, anti‐diabetic, anti‐inflammatory, and antiviral like anti‐HIV and anti‐fungal. A number of reviews covering the important aspects of benzimidazoles such as pharmacological activities, SAR studies, and well‐known methods of synthesis have appeared in the literature. However, green synthetic methods particularly using transition metal (TM) catalysts and their nanoparticles, although being more viable and extensively applied by researchers in the present scenario, have not been exclusively and expansively reviewed. Besides this, the vital precursors required for knitting the skeleton of benzimidazole are mainly o‐aryldiamines. The conventional synthesis generally involved the condensation of these diamines with carbonyl/carboxylic acid derivatives either via high temperature heating or via adding strong acids, mostly resulting in poor yields or mixtures. However, recent trends are replacing these conditions by mild and green conditions through TM catalysts. Therefore, the current review emphasizes on the recent trends adopted in the synthesis of benzimidazoles using condensation reaction of o‐phenylenediamines and various aldehydes/ester/amide/alcohols with TM in a catalytic role in nanoform and under environmentally benign green conditions.

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“…Also, the electronic spectrum of C2 shows the three weak bands. The bands in the 350-450 nm range may be assigned to L →Co charge transfer and 4 T 1 g (F)→ 4 A 2 g(F), 4 T 1 g (F) → 4 T 1 g (P) transitions, respectively. 4 T 1 g(F) → 4 T 2 g(F) transition is not observed in the spectrum of the present complex.…”

Section: Uv-vis Spectramentioning

confidence: 99%

“…They play an important role in inorganic chemistry as they can easily form stable complexes with most of the transition metal ions. One of these ligands is benzimidazolylphenol rings, which is formed via the fusion of benzimidazole and phenol rings, which have been attracted due to their usage in many applications such as anticonvulsant, antiulcer [4], antibacterial, antivirals, antifungals, anticancers [5], antihistaminics and antihypertensive [6]. Benzimidazolylphenols by a large number of carbonyl compounds and amines have been prepared [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and DFT calculations of Novel Mononuclear Nickel (II), Cobalt (II) and Iron (II) Complexes derived from 2-(1H-benzimidazol-2-yl)- phenol Ligand

Haghverdi

Tadjarodi

2016

Proceedings of the 20th International Electronic Conference on Synthetic Organic Chemistry

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In this study, the novel mononuclear complexes, K 2 [Ni (L) 2 Cl 2 ]. 2H 2 O (C1), K 2 [Co (L) 2 Cl 2 ]. H 2 O (C2) and K 2 [Fe (L) 2 Cl 2 ]. 4H 2 O (C3), was L is the 2-(2-hydroxyaryl)-1H-benzimidazole, have been synthesized and characterized. The structures of these compounds were approved by FT-IR, UV-Vis, 1 H-, 13 C-NMR, ICP and elemental analyses (C, H and N). The purity of the compounds was ascertained by melting point (m.p.) and TLC. Based on the combined experimental and theoretical studies, the structure of all compounds are six-coordinated octahedral. The geometry optimization, , stability of the compounds and vibrational frequency calculations of the compounds were carried out in Gaussian 09 program using B3LYP/TZVP level of theory.

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Synthesis of Benzimidazoles via Iron-Catalyzed Aerobic Oxidation Reaction of Imine Derivatives with o-Phenylenediamine

Cited by 15 publications

References 22 publications

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

<strong>Synthesis, Characterization and DFT calculations of Novel Mononuclear Nickel</strong> <strong>(II), Cobalt (II) and Iron</strong> <strong>(II) Complexes derived from 2-(1H-benzimidazol-2-yl)-</strong> <strong>phenol Ligand </strong>

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