63777-68-4

Usage

Classification

Aromatic heterocyclic compound.

Structure

Composed of a benzene ring fused to a 1,2,3-triazole ring and a phenethyl group.

Research applications

Widely used in neuroscience research.

Function

Potent and selective P2X7 receptor agonist.

Biological role

P2X7 receptors are involved in the regulation of immune responses and inflammation.

Therapeutic potential

Possible treatment for chronic pain, neuroinflammation, and neurodegenerative disorders.

Upstream product

• 71878-80-3 1-(methoxymethyl)-1H-benzotriazole 
• 6921-34-2 benzylmagnesium chloride 
• 127236-78-6 N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide 
• 95-14-7 1,2,3-Benzotriazole 
• 103-63-9 1-phenyl-2-bromoethane 
• 54187-96-1 1-(chloromethyl)-1H-benzotriazole 
• 1449418-23-8 1-(2-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)ethyl)-1H-benzo[d][1,2,3]triazole 
• 88-73-3 2-Chloronitrobenzene 
• 64-04-0 phenethylamine 
• 100870-32-4 N-(2-Phenylethyl)-2-nitroaniline 
• 111198-03-9 1-((phenylthio)methyl)-1H-benzo[d][1,2,3]triazole 
• 19213-23-1 1-((pyrrolidin-1-yl)methyl)-1H-benzo[d][1,2,3]triazole 
• 147861-08-3 1-iodomethylbenzotriazole 
• 111198-12-0 1-(2-phenyl-1-phenylthioethyl)benzotriazole 

Relevant academic research and scientific papers

Stereoselective radical azidooxygenation of alkenes

Radical azidooxygenation of various alkenes is described. A readily prepared N3-iodine(III) reagent acts as a clean N3-radical precursor. Radical generation is achieved with TEMPONa acting as a mild organic reducing reagent. The C-radical generated after N3-radical addition is efficiently trapped by in situ generated TEMPO. Yields are good to excellent, and for cyclic systems azidooxygenation occurs with excellent diastereoselectivity.

Aqueous micellar medium in organic synthesis: Alkylations and Michael reactions of benzotriazole

The feasibility of aqueous micelles of cetyltrimethylammonium bromide in catalyzing C-N bond formation has been studied with respect to N-alkylations of benzotriazole (Bt). Alkylations with various alkylating agents and the addition of Bt across activated double bonds in the Michael fashion occurred successfully in fair-to-good yields in the aqueous micellar regime. These reactions provided a mixture of N-1 and N-2 alkylated products, with a marked preference for N-1 over N-2 isomers. Micellar catalysis has been evaluated experimentally to indicate over a 50% micellar contribution to these alkylations in contrast to their aqueous counterparts. Since, N-alkyl benzotriazoles are of potential biological interest, the present micellar procedure offers a convenient alternative to other available methods.

A Novel Selective Route to 1-Substituted Benzotriazoles via Lithiation of Simple 1-Alkylbenzotriazoles

1-Methylbenzotriazole (2a) is lithiated readily with butyllithium or LDA at the methyl group to 4 and the subsequent reaction with various electrophiles provides 1-substituted benzotriazoles 5.Other 1-(n-alkyl)benzotriazoles 2 also undergo lithiation with LDA, the carbanions can be trapped with alkyl halides giving benzotriazoles 6 bearing secondary alkyl groups on the N-1 atom.On standing in the absence of electrophiles, all the lithium derivatives decompose to afford complex mixtures. - Key Words: Benzotriazoles, 1-alkyl / Lithiation / Haloalkanes

Benzotriazol-1-ylmethylammonium Salts Synthesis and Reactivity

Benzotriazol-1-ylmethylamines on treatment with alkylating agents afford benzotriazol-1-ylmethylammonium salts, also available from reactions of chloromethylbenzotriazole with tertiary amines.In deuterated solvents under basic conditions the methylene protons of these salts exchange with deuterium.At elevated temperatures, an alkyl group substituent migrated from the ammonium center to the benzotriazolyl N-3.Reactions of the salts with Grignard reagents afforded various products arising from substitution of the ammonium moiety and/or from attack on the benzotriazolyl N-3 or on the benzenoid ring.

Reactions of 1-(α-Alkoxyalkyl)- and 1-(α-(Aryloxy)alkyl)benzotriazoles with the Grignard Reagents. A New and Versatile Method for the Preparation of Ethers

1-(α-Alkoxyalkyl)benzotriazoles deriving from aldehydes (other than formaldehyde), or from ketones, react with Grignard reagents at 110 deg C to provide a high-yielding, general synthesis of dialkyl and aryl ethers.Under similar conditions, 1-(alkoxymethyl)- and 1-((aryloxy)methyl)benzotriazoles give, by a different cleavage pattern of the N-C-O grouping, 1-alkylbenzotriazoles and N,N'-dialkyl-o-phenylenediamines.The 1-(α-alkoxyalkyl)benzotriazoles are easily prepared: (a) by condensation of benzotriazole, an aldehyde, and an alcohol under water-removing conditions; (b) by condensation of a 1-(α-chloroalkyl)benzotriazole with a sodium or potassium alkoxide or aryloxide; and (c) by condensatioon of an acetal or a ketal with benzotriazole.All the 1-(α-alkoxyalkyl)benzotriazoles and dialkyl or alkyl aryl ethers obtained were fully characterized by their 1H and 13C NMR spectra.

The Chemistry of N-Substituted Benzotriazoles. Part 1. 1-(Chloromethyl)-benzotriazole

The N-chloromethyl group of 1-(chloromethyl)benzotriazole undergoes nucleophilic substitution by carbon, nitrogen, phosphorus, oxygen, and sulphur nucleophiles. α-Lithiation was achieved in high yield in 1-phenylthiomethyl-, 1-phenylsulphinylmethyl-, and 1-(phenylsulphonylmethyl)benzotriazoles and the lithio derivatives reacted with a variety of electrophiles.New benzotriazolium salts were prepared by quaternization of the N-3 nitrogen with methyl iodide.