4887-83-6

Usage

Synthesis Reference(s)

Tetrahedron Letters, 5, p. 2999, 1964 DOI: 10.1002/lipi.19640660210

Upstream product

• 64-18-6 formic acid 
• 2687-25-4 3-methyl-1,2-benzenediamine 
• 20353-93-9 [3-(dimethylamino)-2-azaprop-2-en-1-ylidene]-dimethylammonium chloride 
• 78-84-2 isobutyraldehyde 
• 4885-02-3 Dichloromethyl methyl ether 
• 1445-45-0 Trimethyl orthoacetate 
• 149-73-5 trimethyl orthoformate 
• 73902-59-7 N¹-benzyl-4-methylbenzimidazole 
• 73902-60-0 N³-benzyl-4-methylbenzimidazole 
• 67-56-1 methanol 
• 570-24-1 2-Methyl-6-nitroaniline 
• 68-12-2 N,N-dimethyl-formamide 
• 4252-31-7 N-formylbenzamide 
• 27231-33-0 7-methyl-1H-benzo[d]imidazole-2-thiol 

Downstream Products

• 73902-60-0 N³-benzyl-4-methylbenzimidazole 
• 73902-59-7 N¹-benzyl-4-methylbenzimidazole 
• 172839-53-1 4-methyl-1H-benzimidazole-1-(3-methyl)propanenitrile 
• 1300582-78-8 6-bromo-2-[(4-methyl-1H-benzo[d]imidazol-1-yl)methyl]-3-phenyl-4H-chromen-4-one 
• 1300582-80-2 2-[(4-methyl-1H-benzo[d]imidazol-1-yl)methyl]-3-phenyl-4H-chromen-4-one 
• 1351990-76-5 ethyl 4-(4-methyl-1H-benzo[d]imidazol-1-yl)benzoate 
• 667919-12-2 4-methyl-1-phenyl-1H-benzo[d]imidazole 
• 1476730-66-1 C₁₇H₁₈N₂ 
• 17583-45-8 1,7-dimethyl-1H-benzo[d]imidazole 
• 32863-32-4 benzo[c][1,2,5]oxadiazole-4-carbaldehyde 
• 72803-02-2 darodipine 
• 32863-30-2 4-(bromomethyl)benzo[c][1,2,5]oxadiazole 
• 132873-77-9 4-(bromomethyl)benzimidazole-1-carboxylic acid,1,1-dimethylethyl ester 

Relevant academic research and scientific papers

Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes

Strategies commonly used for the synthesis of functionalised bicyclo[1.1.1]pentanes (BCP) rely on the reaction of [1.1.1]propellane with anionic or radical intermediates. In contrast, electrophilic activation has remained a considerable challenge due to t

Reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to synthesize 1H-benzoimidazole derivatives

A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH3NH3 promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramolecular nucleophilic addition-elimination for the formation of target product. In this process, BH3NH3 served multifunctional roles, acting as a reducing agent and a formylation catalyst.

K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles

We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.

Synthesis method of ammonium acetate mediated benzimidazole compound

The invention discloses a synthesis method of a benzimidazole compound mediated by ammonium acetate. The synthesis method comprises the following steps: adding an o-phenylenediamine compound, dimethylsulfoxide, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at 130-150 DEG C, cooling the reaction product to room temperature after the reaction is finished, and carrying out separation and purification on the product to obtain the benzimidazole compound. The invention develops a method for synthesizing a benzimidazole compound under the mediation of ammonium acetate by taking DMSO as a carbon source and an oxidant and an o-phenylenediamine compound as a substrate under the condition of no metal catalyst. The synthesis method does not need a metal catalyst, and the required carbon source and oxidant have the characteristics of low toxicity, low price, easiness in obtaining, stable performance and the like. The method has the advantages of easiness inoperation, few steps, mild reaction conditions, better functional group tolerance and the like, and provides a new valuable way for synthesizing benzimidazole compounds.

METALLOENZYME INHIBITOR COMPOUNDS

Provided are compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.

Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical

A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.

Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides

A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is

Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones

N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.

Supported Rhodium (Rh@PS) Catalyzed Benzimidazoles Synthesis Using Ethanol/Methanol as C2H3/CH Source

An effective and stable polystyrene supported rhodium (Rh@PS) nano-catalyst has been synthesized by following reduction-deposition approach and applied for the selective benzimidazoles synthesis from 1,2-phenylenediamines and ethanol/methanol as C2H3/CH source. The ethanol/methanol in the presence of trace amounts of aerobic oxygen under Rh@PS catalysed condition, first participated in oxidation of alcohol followed by consecutive condensation, cyclization and hydrogen elimination reactions with 1,2-phenylenediamine gave the desired products in good yields. The Rh@PS catalyst in a single system performed both oxidation and reduction reactions in a selective/specific manner and applied for large substrate scope. Easy recovery, handling, stability, recyclability of the catalyst and less chance of metal contamination with the products are the added advantages of the process. (Figure presented.).

In Situ Formation of Frustrated Lewis Pairs in a Water-Tolerant Metal-Organic Framework for the Transformation of CO2

Frustrated Lewis pairs (FLPs) consist of sterically hindered Lewis acids and Lewis bases, which provide high catalytic activity towards non-metal-mediated activation of “inert” small molecules, including CO2 among others. One critical issue of homogeneous FLPs, however, is their instability upon recycling, leading to catalytic deactivation. Herein, we provide a solution to this issue by incorporating a bulky Lewis acid-functionalized ligand into a water-tolerant metal-organic framework (MOF), named SION-105, and employing Lewis basic diamine substrates for the in situ formation of FLPs within the MOF. Using CO2 as a C1-feedstock, this combination allows for the efficient transformation of a variety of diamine substrates into benzimidazoles. SION-105 can be easily recycled by washing with MeOH and reused multiple times without losing its identity and catalytic activity, highlighting the advantage of the MOF approach in FLP chemistry.