Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Sun, Xiang; Lv, Xiao-Hui; Ye, Lin‐miao; Hu, Yu Lin; Chen, Yanyan; Zhang, Xue‐Jing; Yan, Ming

doi:10.1039/c5ob00904a

Cited by 39 publications

(17 citation statements)

References 31 publications

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“…This usually require strong acid, high temperature, and sometimes photo-irradiation conditions, precious metal salts 7 , molecular oxygen 8 , or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone as oxidant 9 . Iridium-catalyzed acceptor-less dehydrogenative coupling of tertiary amines was recently reported as novel strategy for the synthesis of benzimidazole 10 .…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Characterization and Antimicrobial Activity of 2-Alkanamino Benzimidazole Derivatives

Ajani¹,

Aderohunmu²,

Olorunshola³

et al. 2016

Orient. J. Chem

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Benzimidazole derivatives are known to represent a class of medicinally important compounds which are extensively used in drug design and catalysis. A series of 2-substituted benzimidazole derivatives 10a-i was herein synthesized from the reaction of o-phenylenediamine with some amino acids using ameliorable pathway. The chemical structures of the synthesized compounds were confirmed by IR, UV, 1 H-NMR, 13 C-NMR, Mass spectral and analytical data. The compounds were investigated for their antimicrobial activity alongside gentamicin clinical standard. The results showed that this skeletal framework exhibited marked potency as antimicrobial agents. The most active compound was 1H-benzo[d]imidazol-2-yl)methanamine, 10a.

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Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Characterization and Antimicrobial Activity of 2-Alkanamino Benzimidazole Derivatives

Ajani¹,

Aderohunmu²,

Olorunshola³

et al. 2016

Orient. J. Chem

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“…3,16,29 There are drawbacks to reported syntheses of alicyclic ring-fused benzimidazoles such as requirements for transition metals, [1][2][3][4][5][6][7][8][9] prior synthesis of cyclization precursors, [10][11][12][13][14][15][16][17] full equivalents of strong base, [17][18][19][20] high molar mass hypervalent iodine reagents, 21 and the formation of mixtures of isomeric products. 22 The most convenient protocol remains the traditional oxidative cyclization of o-cyclic amine substituted anilines, which was first reported in the early 1960s using hydrogen peroxide in the presence of trifluoroacetic acid.…”

Section: Introductionmentioning

confidence: 99%

Greener synthesis using hydrogen peroxide in ethyl acetate of alicyclic ring-fused benzimidazoles and anti-tumour benzimidazolequinones

Sweeney

Gurry

Keane

et al. 2017

Tetrahedron Letters

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“…The formamide has less steric bulk than the acetamide forming a mixture of the thermodynamic and kinetic products. The reaction was extended to the synthesis of pyrrolo-, pyrido-, and azepino-[1,2- a ]benzimidazoles, without the requirement for a ligand ( Scheme 6 b), but was less successful for making morpholino- and piperazino-ring-fused analogues [ 48 ].…”

Section: Syntheses Of Ring-fused Benzimidazoles and Imidazobenzimidazolesmentioning

confidence: 99%

Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles

et al. 2021

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This review article provides a perspective on the synthesis of alicyclic and heterocyclic ring-fused benzimidazoles, imidazo[4,5-f]benzimidazoles, and imidazo[5,4-f]benzimidazoles. These heterocycles have a plethora of biological activities with the iminoquinone and quinone derivatives displaying potent bioreductive antitumor activity. Synthesis is categorized according to the cyclization reaction and mechanisms are detailed. Nitrobenzene reduction, cyclization of aryl amidines, lactams and isothiocyanates are described. Protocols include condensation, cross-dehydrogenative coupling with transition metal catalysis, annulation onto benzimidazole, often using CuI-catalysis, and radical cyclization with homolytic aromatic substitution. Many oxidative transformations are under metal-free conditions, including using thermal, photochemical, and electrochemical methods. Syntheses of diazole analogues of mitomycin C derivatives are described. Traditional oxidations of o-(cycloamino)anilines using peroxides in acid via the t-amino effect remain popular.

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Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Cited by 39 publications

References 31 publications

Facile Synthesis, Characterization and Antimicrobial Activity of 2-Alkanamino Benzimidazole Derivatives

Facile Synthesis, Characterization and Antimicrobial Activity of 2-Alkanamino Benzimidazole Derivatives

Greener synthesis using hydrogen peroxide in ethyl acetate of alicyclic ring-fused benzimidazoles and anti-tumour benzimidazolequinones

Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles

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