32046-51-8

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-5-NITRO-1,3-BENZOXAZOLE is used as a building block for the synthesis of various pharmaceuticals, leveraging its bioactive properties and versatile reactivity to create new and effective medications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-METHYL-5-NITRO-1,3-BENZOXAZOLE is employed as a precursor in the development of agrochemicals, contributing to the creation of compounds that can enhance crop protection and yield.
Used in Research and Development:
2-METHYL-5-NITRO-1,3-BENZOXAZOLE is utilized as a precursor in research and development for the synthesis of other compounds, taking advantage of its characteristic properties to explore new chemical pathways and applications.

InChI:InChI=1/C8H6N2O3/c1-5-9-7-4-6(10(11)12)2-3-8(7)13-5/h2-4H,1H3

Upstream product

• 32403-66-0 2-(2,4-dinitro-phenoxy)-propionic acid 
• 108-24-7 acetic anhydride 
• 99-57-0 2-hydroxy-5-nitroaniline 
• 95-21-6 2-methyl-1,3-benzoxazole 
• 55682-66-1 deca-1,3-diyne 
• 1254970-95-0 N-nitro-О-(4-nitrophenyl)hydroxylamine 
• 75-05-8 acetonitrile 
• 78-39-7 Triethyl orthoacetate 
• 123-54-6 acetylacetone 
• 1450-76-6 1-(2-hydroxy-5-nitrophenyl)ethanone 
• 10403-47-1 2-bromo 5-nitroaniline 
• 90221-50-4 N-(2-bromo-5-nitrophenyl)acetamide 
• 1247949-39-8 2-(1-iminoethyl)-4-nitrophenol 
• 97-60-9 2-acetamido-4-nitrophenol 

Downstream Products

• 72745-76-7 5-amino-2-methylbenzoxazole 
• 1400811-42-8 2-methyl-5-benzoxazolylphthalimide 

Relevant academic research and scientific papers

NMR recognition studies of C·G base pairs by new easily accessible heterobicyclic systems

Recognition of DNA duplexes by triplex forming oligonucleotides (TFO) is limited to DNA homopurine sequences. As a first step to overcome this limitation we report here NMR recognition studies of the C·G base pair by new heterocyclic systems, derived from benzimidazole and benzoxazole units bearing an urea donor moiety, designed to bound to the 4-amino group of the cytosine and the O4- and N7-atoms of the guanosine bases, respectively.

Metal free montmorillonite KSF clay catalyzed practical synthesis of benzoxazoles and benzothiazoles under aerobic conditions

An efficient method for the synthesis of benzoxazoles and benzothiazoles via montmorillonite KSF clay catalyzed condensation reaction between 2-aminophenols or 2-aminothiophenols and β-diketones is reported. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on aryls. The reaction is metal free and proceeds without the exclusion of air or moisture, and further the catalyst can be recycled up to 3–5 catalytic cycles.

Functionalized C-nucleosides as remarkable RNA binders: Targeting of prokaryotic ribosomal A-site RNA

RNA represents an extremely promising and yet challenging therapeutic target. Here, we report the design of a series of C-nucleosides as original RNA binders. Some of them bind strongly and selectively to A-site prokaryotic ribosomal RNA.

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.

Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement

A Beckmann-type rearrangement of o-hydroxy and o-aminoaryl N-H ketimines has been developed to prepare benzoxazoles and N-Ts benzimidazoles, respectively. The ketimine derivatives were easily prepared by condensation of ammonia with the corresponding ketones and (diacetoxyiodo)benzene was found to act as an efficient oxidant to trigger the [1,2]-aryl migration towards the formation of the desired heterocycles. Depending on the substitution pattern, the results revealed another mechanistic pathway through which benzisoxazoles or 1H-indazoles could be formed. The Beckmann-type rearrangement strategy was applied to the synthesis of benzimidazole-containing biorelevant targets such as chlormidazole and clemizole.

Acid Catalyzed Direct-Amidation-Dehydrocyclization of 2-Hydroxy-acetophenones to Benzoxazoles by a One-Pot Sustainable Synthesis

A series of 2-methyl-benzoxazoles have been synthesized starting from 2-hydroxy-acetophenones via a one-pot three steps reaction. Hydroxylamonium salt has been used as amidation agent. The reaction occurs with different anions, but the best results is achieved with hydroxylamonium hydrchloride. Despite the number of consecutive stages, the reaction is highly selective. Mild reaction conditions and various solvents can be used, but trifluoroacetic acid is the preferred. Almost, complete recovery of the trifluoroacetic acid can be achieved by vacuum distillation. The role of trifluoroacetic acid, as well as, of the hydroxylamonium salt suggests a cooperative effect leading to high selective formation of 2-methyl-benzoxazoles. Graphical Abstract: One-pot TFA catalyzed synthesis of benzoxazoles starting from 2-hydroxyacetophenones. (Chemical Equation Presented).

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

ANTI-INFECTIVE COMPOUNDS

The present invention relates to small molecule compounds having the general formula (I): wherein A is a moiety selected from the group consisting of formulae (A) to (K) and their use in the treatment of bacterial infections, in particular Tuberculosis.

Synthesis of benzoxazoles from 2-aminophenols and β-diketones using a combined catalyst of br?nsted acid and copper iodide

Cyclization reactions of 2-aminophenols with β-diketones catalyzed by a combination of Br?nsted acid and CuI are presented. Various 2-substituted benzoxazoles were obtained through these reactions. Different substituents such as methyl, chloro, bromo, nitro, and methoxy on 2-aminophenol are tolerated under the optimized reaction conditions.

ANTI-VIRAL COMPOUNDS

Described herein are compounds and related compositions for the treatment of viral infections, including RNA viral infection, and compounds that can modulate the RIG-I pathway in vertebrate cells,including compounds that can activate the RIG-I pathway.