7724-48-3

Usage

Uses

Used in Pharmaceutical Research:
2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole is used as a building block for the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows it to be a key component in the development of new drugs.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole is utilized as an intermediate. Its properties make it instrumental in the synthesis of compounds with potential therapeutic applications.
Used in Drug Development:
2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole is used as a potential lead compound in drug development. Its diverse biological activities make it a promising candidate for further research and potential inclusion in new medications.
Used in Organic Synthesis:
This chemical is also used in organic synthesis, where its fused ring system contributes to the creation of complex organic compounds for various applications.

InChI:InChI=1/C10H10N2/c1-2-5-9-8(4-1)11-10-6-3-7-12(9)10/h1-2,4-5H,3,6-7H2

Upstream product

• 96-48-0 4-butanolide 
• 95-54-5 1,2-diamino-benzene 
• 135347-86-3 (3-Fluoro-phenyl)-pyrrolidin-(2Z)-ylidene-amine 
• 201230-82-2 carbon monoxide 
• 55899-43-9 N-allyl-1,2-phenylenediamine 
• 191542-43-5 1-<3-(phenylselanyl)propyl>-2-(phenylsulfanyl)-1H-benzimidazole 
• 223928-08-3 1-<3-(phenylselanyl)propyl>-1H-benzimidazole 
• 51-17-2 benzoimidazole 
• 109-70-6 1.3-chlorobromopropane 
• 286407-95-2 1-(2-bromoethyl)-2-methyl-1H-benzimidazole 
• 19018-22-5 1-allylbenzimidazole 
• 2403-66-9 2-(3-hydroxypropyl)benzimidazole 
• 895581-98-3 2-chloro-1-[(3-phenylselanyl)propyl]-1H-benzo[d]imidazole 
• 895582-01-1 4-({1-[(3-phenylselanyl)propyl]-1H-benzo[d]imidazol-2-yl}sulfanyl)benzoic acid 

Downstream Products

• 21627-58-7 2-(pyrrolidin-1-yl)-phenylamine 
• 39161-58-5 1,2,3,4,5,6-hexahydro-benzo[b][1,4]diazocine 

Relevant academic research and scientific papers

Electrochemical Synthesis of Benzo[ d]imidazole via Intramolecular C(sp3)-H Amination

An electrochemical dehydrogenative amination for the synthesis of benzimidazoles was developed. This electrosynthesis method could address the limitations of the C(sp3)-H intramolecular amination synthesis reaction and provide novel access to obtain 1,2-disubstituted benzimidazoles without transition metals and oxidants. Under undivided electrolytic conditions, various benzimidazole derivatives could be synthesized, exhibiting functional group tolerance.

1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates

Benzimidazoles are common in nature, medicines, and materials. Numerous strategies for preparing 2-arylbenzimidazoles exist. In this work, 1,2-disubstituted benzimidazoles were prepared from various mono- and disubstituted ortho-phenylenediamines (OPD) by iron-catalyzed oxidative coupling. Specifically, O2 and FeCl3·6H2O catalyzed the cross-dehydrogenative coupling and aromatization of diarylmethyl and dialkyl benzimidazole precursors. N,N′-Disubstituted-OPD substrates were significantly more reactive than their N,N-disubstituted isomers, which appears to be relative to their propensity for complexation and charge transfer with Fe3+. The reaction also converted N-monosubstituted OPD substrates to 2-substituted benzimidazoles; however, electron-poor substrates produce 1,2-disubstituted benzimidazoles by intermolecular imino-transfer. Kinetic, reagent, and spectroscopic (UV-vis and EPR) studies suggest a mechanism involving metal-substrate complexation, charge transfer, and aerobic turnover, involving high-valent Fe(IV) intermediates. Overall, comparative strategies for the relatively sustainable and efficient synthesis of 1,2-disubstituted benzimidazoles are demonstrated.

Synthesis of rutaecarpine alkaloids: Via an electrochemical cross dehydrogenation coupling reaction

Substrates are directly oxidized at the anode without using any metal catalyst and oxidant to obtain a series of nitrogen heterocyclic compounds, including benzimidazoles and quinolinones. These compounds are highly tolerant to various functional groups and heterocycle-containing substrates. In addition, natural alkaloids, such as rutaecarpine and deoxyvasicinone, can be synthesized by this method.

Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives

The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.

BENZIMIDAZOLE COMPOUND AND SYNTHESIS METHOD THEREOF

PROBLEM TO BE SOLVED: To provide a novel benzimidazole compound having tetracyclic condensed ring and a synthesis method thereof. SOLUTION: A benzimidazole compound is represented by the formula (I). A method for synthesizing the benzimidazole compound represented by the formula (I) includes the step of reacting ortho-phenylene diamine and a lactone compound and further reacting the resulting benzimidazole compound with the lactone compound. In the formula, R1 and R4 are each independently H, a methyl group or an ethyl group excluding that two of R4 are ethyl groups or methyl groups at same time, R2 and R3 are each independently H or a methyl group, m and n are integers of 1 to 2 and n is 1 when m is 2. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Synthesis of 1,2-disubstituted benzimidazoles using an aza-Wittig-equivalent process

A synthetic approach for 1,2-disubstituted benzimidazoles has been successfully designed based on effective C-N bond construction, which demonstrated mild reaction conditions and excellent yields. The method involves treating derivatives of o-phenylenediamine with tert-butanesulfoxide and NBS under acidic conditions, which undergoes an aza-Wittig-equivalent process to afford the desired products. Using this method, a series of benzimidazoles containing multiple functional groups with varying electronic effects have been successfully constructed.

Metal-Free Sequential C(sp2)-H/OH and C(sp3)-H Aminations of Nitrosoarenes and N-Heterocycles to Ring-Fused Imidazoles

Hydrogen bond assisted ortho-selective C(sp2)-H amination of nitrosoarenes and subsequent α-C(sp3)-H functionalization of aliphatic amines is achieved under metal-free conditions. The annulation of nitrosoarenes and 2-hydroxy-C-nitroso compounds with N-heterocycles provides a facile excess to a wide range of biologically relevant ring-fused benzimidazoles and structurally novel polycyclic imidazoles, respectively. Nucleophilic aromatic hydrogen substitution (SNArH) was found to be preferred over classical SNAr reaction during the C(sp2)-H amination of halogenated nitrosoarenes.

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

Environmentally-friendly and cost effective hydrogen peroxide in ethyl acetate was used to prepare in high yields pyrrolo[1,2-a]benzimidazoles from commercial o-(pyrrolidin-1-yl)anilines without the requirement for organic-aqueous extraction and chromatography. Six, seven and eight membered ring-fused analogues were similarly obtained in high yields with methanesulfonic acid required for the pyrido[1,2-a]benzimidazole. Anti-tumour benzimidazolequinone derivatives were obtained in high yield via the cyclization of 3,6-dimethoxy-2-(cycloamino)anilines.

Formic acid as a sustainable and complementary reductant: An approach to fused benzimidazoles by molecular iodine-catalyzed reductive redox cyclization of: O -nitro- t -anilines

Molecular iodine was found to be an excellent catalyst for reductive redox cyclization of o-nitro-t-anilines 1 into fused tricyclic or 1,2-disubtituted benzimidazoles 2. A range of functional groups such as halides (F, Cl, Br), methoxy, ester, trifluoromethyl, cyano, pyridine and even nitro groups were tolerated using formic acid as a clean, safe, user-friendly and complementary reductant. When iodine was used in a stoichiometric amount (50 mol%), the methodology allowed the direct synthesis of benzimidazole hydroiodides 2·HI in high yields by simple precipitation from the reaction mixture.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.