6926-44-9

Usage

Uses

Used in Chemical Synthesis:
Benzene, (2-azidoethyl)is used as a reactant in the preparation of disubstituted triazoles. The application reason is its ability to participate in ruthenium-catalyzed cycloaddition reactions with terminal alkynes and azides, leading to the formation of disubstituted triazoles, which are important compounds in various fields such as pharmaceuticals, materials science, and chemical research.

InChI:InChI=1/C8H9N3/c9-11-10-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 60-12-8 2-phenylethanol 
• 4455-09-8 2-phenylethyl tosylate 
• 55419-66-4 trifluoroacetic acid 2-phenylethyl ester 
• 1927-61-3 2-(2-phenylethoxy)tetrahydro-2H-pyran 
• 64-04-0 phenethylamine 
• 1266134-54-6 2-azido-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium hexafluorophosphate (V) 
• 122-78-1 phenylacetaldehyde 
• 17376-04-4 2-phenethyl iodide 
• 622-24-2 2-phenylethyl chloride 
• 1246367-30-5 benzotriazol-1-yl-sulfonyl azide 
• 20020-27-3 2-phenylethyl mesylate 

Downstream Products

• 64-04-0 phenethylamine 
• 3278-14-6 N-phenethylbenzamide 
• 15795-36-5 N,N-dimethyl-N'-phenethyl-formamidine 
• 156361-34-1 1-Phenethyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester 
• 146039-09-0 Phenethyl-phosphorimidic acid triethyl ester 
• 159979-98-3 5-Amino-1-phenethyl-1H-[1,2,3]triazole-4-carboxylic acid amide 
• 182952-48-3 (5S,6R)-1-(2-Azidoethyl)-5,6-dihydroxycyclohexa-1,3-diene 
• 180045-38-9 3-Phenethyl-5-phenyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one 
• 3240-95-7 (E)-N-(phenylethyl)-1-phenylmethanimine 
• 65259-56-5 phenylacetaldehyde dimethylhydrazone 
• 38427-90-6 N-(t-butoxycarbonyl)phenethylamine 
• 28917-26-2 3-(1-phenethylamino-ethylidene)-dihydro-furan-2-one 

Relevant academic research and scientific papers

Controlling the selectivity of C-H activation in pyridinium triazolylidene iridium complexes: Mechanistic details and influence of remote substituents

Iridium complexes containing a triazolylidene ligand with an appended methylpyridinium site undergo either aromatic C(sp2)-H bond activation or exocyclic C(sp3)-H bond activation of the N-bound methyl group. The selectivity of these

Preparation of highly functionalized 1,5-disubstituted tetrazoles via palladium-catalyzed Suzuki coupling

The preparation of a range of 1,5-disubstituted tetrazoles has been achieved through palladium-catalyzed Suzuki coupling. Using appropriately substituted 5-p-toluenesulfonyltetrazoles as substrates (obtained by cycloaddition of a substituted azide with p-toluenesulfonyl cyanide), this methodology provides access to a variety of highly substituted tetrazoles that would be difficult to access otherwise. The procedure is compatible with functional groups commonly found in drug-like molecules, and has been used to generate a number of compounds of potential biological interest.

ISOINDOLINE COMPOUND, AND PREPARATION METHOD, PHARMACEUTICAL COMPOSITION, AND APPLICATION OF ISOINDOLINE COMPOUND

The present invention relates to an isoindoline compound as represented by general formula (I) and used as a CRBN regulator, and a preparation method, a pharmaceutical composition, and an application of the isoindoline compound. Specifically, a class of polysubstituted isoindoline compound provided in the present invention, as a class of CRL4CRBN E3 ubiquitin ligase regulator having a novel structure, has good anti-tumor activity and immunoregulatory activity, and can be used for preparing drugs for treating diseases associated with a CRL4CRBN E3 ubiquitin ligase.

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including14C and11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.

Synthesis, antimicrobial evaluation, and in silico studies of quinoline—1H-1,2,3-triazole molecular hybrids

Abstract: Antimicrobial resistance has become a significant threat to global public health, thus precipitating an exigent need for new drugs with improved therapeutic efficacy. In this regard, molecular hybridization is deemed as a viable strategy to afford multi-target-based drug candidates. Herein, we report a library of quinoline—1H-1,2,3-triazole molecular hybrids synthesized via copper(I)-catalyzed azide-alkyne [3 + 2] dipolar cycloaddition reaction (CuAAC). Antimicrobial evaluation identified compound 16 as the most active hybrid in the library with a broad-spectrum antibacterial activity at an MIC80 value of 75.39?μM against methicillin-resistant S. aureus, E. coli, A. baumannii, and multidrug-resistant K. pneumoniae. The compound also showed interesting antifungal profile against C. albicans and C. neoformans at an MIC80 value of 37.69 and 2.36?μM, respectively, superior to fluconazole. In vitro toxicity profiling revealed non-hemolytic activity against human red blood cells (hRBC) but partial cytotoxicity to human embryonic kidney cells (HEK293). Additionally, in silico studies predicted excellent drug-like properties and the importance of triazole ring in stabilizing the complexation with target proteins. Overall, these results present compound 16 as a promising scaffold on which other molecules can be modeled to deliver new antimicrobial agents with improved potency. Graphic abstract: [Figure not available: see fulltext.].

TDP-43 Modulation by Tau-Tubulin Kinase 1 Inhibitors: A New Avenue for Future Amyotrophic Lateral Sclerosis Therapy

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease without any effective treatment. Protein TDP-43 is a pathological hallmark of ALS in both sporadic and familiar patients. Post-translational modifications of TDP-43 promote its aggre

Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization

Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.

NURR1 RECEPTOR MODULATORS

Described herein, inter alia, are Nurr1 receptor modulators and uses thereof. In an aspect is provided a method for treating a disease associated with dysregulation and/or degeneration of dopaminergic neurons in the central nervous system of a subject in need thereof, the method including administering to the subject in need thereof a therapeutically effective amount of a compound described herein.

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.