66519-70-8

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 57710-80-2 1-benzyloxycarbonyl-1Hbenzo[d][1.2.3]triazole 
• 6085-94-5 1-benzyl-1,2,4-triazole 
• 100-51-6 benzyl alcohol 
• 43183-36-4 1-(trimethylsilyl)-1H-benzotriazole 
• 68985-05-7 1,1′-carbonylbis-benzotriazole 

Relevant academic research and scientific papers

Mitsunobu reaction of 1,2,3-NH-triazoles: A regio- and stereoselective approach to functionalized triazole derivatives

The Mitsunobu reaction was used in the preparation of chiral triazole derivatives. The reactions gave good to excellent yields with large substrate scope. Complete stereochemistry inversion was obtained, making this strategy one practical approach for the

Green and efficient protocol for N-alkylation of benzotriazole using basic ionic liquid [Bmim]OH as catalyst under solvent-free conditions

N-Alkylation of benzotriazole bearing an acidic hydrogen atom attached to nitrogen with alkyl halides is accomplished in basic ionic liquid [Bmim]OH (1-butyl-3-methylimidazolium hydroxide) under solvent-free conditions. The procedure is convenient and efficient and generally affords the N-alkylated product. Taylor & Francis Group, LLC.

TBAF-assisted copper-catalyzed N-arylation and benzylation of benzazoles with aryl and benzyl halides under the ligand/base/ solvent-free conditions

(Equation Presented) TBAF-assisted N-arylation and benzylation of benzazoles such as 1H-benzimidazole, 1H-indole, and 1H-benzotriazole with aryl and benzyl halides have been demonstrated under the ligand/base/solvent-free conditions. In the presence of CuBr2 and TBAF (n-Bu4NF), the azoles underwent N-arylation and benzylation with aryl and benzyl halides smoothly in moderate to good yields. It is noteworthy that the reaction is conducted under the ligand/base/solvent-free conditions.

Organic reactions in ionic liquids: An efficient method for the N-alkylation of benzotriazole

The N-alkylation of benzotriazole with alkyl halides proceeds efficiently in the presence of potassium hydroxide in ionic liquid 1-butyl-3- methylimidazolium tetrafluoroborate ([Bmim][BF4]).

Organic reactions in ionic liquids: A simple highly regioselective or regiospecific substitutions of benzotriazole

In the absence of any added base in ionic liquids [Bmim][BF4], benzotriazole replaces the halogen atom of an α-halogenated ketone or α-halogenated carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer, and

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.

SELECTIVE ALKYLATIONS OF 1,2,4-TRIAZOLE AND BENZOTRIAZOLE IN THE ABSENCE OF SOLVENT

Alkylation of 1,2,4-triazole and benzotriazole has been performed either in basic media under solvent free phase transfer catalysis conditions or in the absence of base by conventional and microwave heating.Several parameters affecting the selectivity have been studied.In the case of triazole alkylation, microwave irradiation produces specific (non thermal) effects both on reactivity and selectivity.

A simple, versatile synthetic route to N-1-aryl-, -heteroaryl-, -acylmethyl-, -carboxymethyl- and -alkyl-benzotriazoles via regiospecific or highly regioselective substitutions of benzotriazole

In the absence of any added base in refluxing benzene or toluene, benzotriazole replaces the halogen atom of an α-halogenated ketone or a carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer. 2-Bromopyridine and 1-chloro-2,4-dinitrobenzene reacted similarly with benzotriazole to afford the corresponding N-1-substituted benzotriazole derivatives in quantitative yields. Alkyl halides reacted regioselectively to afford the N-1-alkylbenzotriazoles in ratios of more than 10 to 1 over the N-2 isomers. An α-(benzotriazol-1-yl)carboxylic ester was hydrolyzed into the corresponding carboxylic acid, which upon heating underwent smooth decarboxylation into the corresponding 1-alkylbenzotriazole.

STUDIES ON THE THERMAL DECARBOXYLATION OF 1-ALKOXYCARBONYLBENZOTRIAZOLES

1-Alkoxycarbonylbenzotriazoles on thermolysis lose carbon dioxide; the decarboxylation is accompanied by the formation of a mixture of 1- and 2-alkylbenzotriazoles, with the N-1 isomer predominating over the N-2 isomer in all cases.A cross-over experiment

An improved method for the N-alkylation of benzotriazole and 1,2,4-triazole

The N-alkylation of benzotriazole and 1,2,4-triazole with alkyl halides proceeds efficiently in the presence of sodium hydroxide in N,N-dimethylformamide.