79002-39-4

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C9H5NO/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-5H

Upstream product

• 23145-07-5 5-bromobenzofuran 
• 544-92-3 copper(I) cyanide 
• 60770-67-4 5-iodobenzofuran 
• 557-21-1 zinc(II) cyanide 
• 60770-65-2 5-(methylthio)benzofuran 
• 33148-47-9 4-allyloxy-benzonitrile 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 10035-16-2 benzofuran-5-carbaldehyde 
• 129969-69-3 1-bromo-4'-(2,2-dimethoxyethoxy)benzene 
• 106-41-2 4-bromo-phenol 
• 90923-69-6 3-allyl-4-hydroxy-benzonitrile 
• 767-00-0 4-cyanophenol 

Downstream Products

• 10035-16-2 benzofuran-5-carbaldehyde 
• 190775-71-4 1-(benzofuran-5-yl)ethan-1-one 
• 37798-08-6 (1-benzofuran-5-yl)methanamine 
• 1307230-52-9 5-(3-(benzofuran-5-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile 
• 1307231-09-9 N-hydroxybenzofuran-5-carboximidamide 

Relevant academic research and scientific papers

Nickel-Catalyzed Cyanation of Aryl Thioethers

A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Design and synthesis of C3-symmetric molecules containing oxepine and benzofuran moieties via Metathesis

We report a new synthetic strategy to C3-symmetric star-shaped phenyl and triazine central cores bearing oxepine and benzofuran ring systems. In this regard, we have explored the application of metathetic strategy to construct C3-sym

Method for converting aromatic aldehyde into aromatic nitrile by using sulfur powder promoted inorganic ammonium as nitrogen source (by machine translation)

The invention discloses a method for converting aromatic aldehyde into aromatic nitrile. The method is conversion of high yield of aromatic aldehyde one-pot reaction of sulfur powder promoted inorganic ammonium as a nitrogen source into aromatic nitrile. The method has the advantages of no need of metal participation, no need of strong oxide, compatibility of reaction to air, easiness in amplification to a gram scale and the like, and overcomes the problems of harsh reaction conditions, complex operation, low functional group compatibility and the like in the prior art. (by machine translation)

Difluorocarbene-Based Cyanation of Aryl Iodides

A large number of efficient cyanation methods have been developed because of the wide range of applications of nitriles, but conventional methods usually suffer from the need for a toxic cyanation reagent. Although difluorocarbene chemistry has received increasing attention, the use of difluorocarbene as a sources of the nitrile carbon for nitrile groups remains largely unexplored. We describe a difluorocarbene-based cyanation of aryl iodides promoted by a cheap copper source, Cu(NO 3) 2 ·2.5H 2 O, under an air atmosphere. Ph 3 P + CF 2 CO 2-, an easily available and shelf-stable difluorocarbene reagent, and NaNH 2 are used as the carbon source and the nitrogen source for the nitrile group, respectively. The cyanation protocol is attractive because no toxic reagent is used and performing the reactions under an air atmosphere is operationally convenient.

Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters

The first example of intramolecular ring-opening and reconstruction of cyclobutanone oxime esters via selective C-C bond cleavage leading to the synthesis of 3,4-dihydronaphthalene-2-carbonitriles in the presence of a cheap copper catalyst has been reported. The protocol is distinguished by mild and safe reaction conditions that exclude ligands, oxidants, bases, toxic cyanide salts and tolerates a wide scope of cyclobutanones without compromising their efficiency and scalability. The alternative visible-light-driven photoredox process for this coupling reaction was also uncovered.

Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor

In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.

Identification of 4-(2-furanyl)pyrimidin-2-amines as Janus kinase 2 inhibitors

Janus kinases inhibitor is considered to have therapeutic potential for the treatment of oncology and immune-inflammatory diseases. Two series of 4-(2-benzofuranyl)pyrimidin-2-amine and 4-(4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-yl)pyrimidin-2-amine derivatives have been designed and synthesized. Primary SAR studies resulted in the discovery of a novel class of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine based JAK2 inhibitors with higher potency (IC50of 0.7 nM) and selectivity (>30 fold) to JAK3 kinase than tofacitinib.

NOVEL TRICYCLIC CALCIUM SENSING RECEPTOR ANTAGONISTS FOR THE TREATMENT OF OSTEOPOROSIS

Novel tricyclic compounds of the formula (I): and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing osteoporosis and similar conditions. The compounds are effective as calcium sensing receptor antagonists. Pharmaceutical compositions and methods of treatment are also included.

One-pot synthesis of amidoxime via Pd-catalyzed cyanation and amidoximation

A novel "one-pot" reaction was developed for the synthesis of aryl or heteroaryl-substituted amidoxime compounds containing various functional groups. Fluorescence titration experiments coupled with theoretical analysis revealed that the steric hindrance and electronic effects of substituents influence the binding ability of the amidoxime compounds to uranyl ions. This journal is