100726-41-8Relevant academic research and scientific papers
Novel synthesis of benzotriazolyl alkyl esters: an unprecedented CH2insertion
Elagawany, Mohamed,Maram, Lingaiah,Elgendy, Bahaa
, p. 7564 - 7569 (2021)
We have developed a novel method for the synthesis of benzotriazolyl alkyl esters (BAEs) fromN-acylbenzotriazoles and dichloromethane (DCM) under mild conditions. This reaction is one of few examples to show the use of DCM as a C-1 surrogate in carbon-heteroatom bond formation and to highlight the versatility of using DCM as a methylene building block.
Benzotriazole: A novel synthetic auxiliary
Katritzky, Alan R.,Rachwal, Stanislaw,Hitchings, Gregory J.
, p. 2683 - 2732 (2007/10/02)
Benzotriazole and aldehydes react reversibly to give addition products: in the presence of amines and other NH-compounds water can be eliminated to form products of type Bt-CHR-NR′R″. The latter are versatile intermediates for the preparation of primary, secondary, and tertiary amines and in the alkylation of hydroxylamines, hydrazines, amides, thioamides, and sulfonamides. Polyfunctional amines and other polyfunctional compounds can also be prepared, and they enable significant extending of Mannich reaction. Similar oxygen compounds Bt-CRR′-OR″ enable new syntheses of ethers and esters. Reactions in which benzotriazole is eliminated rather than substituted open up new pathways to enamines, enol ethers, and nitrones. The methodology is capable of extension to a variety of vinylogous systems including benzenoid and heteroaromatic derivatives. In addition to acting as a versatile leaving group, benzotriazolyl residues activate neighboring CH bonds to proton loss and a variety of such applications is described.
A novel synthesis of esters via substitution of the benzotriazolyl group in 1-(benzotriazol-1-yl)alkyl esters with organozinc reagents
Katritzky,Rachwal,Rachwal
, p. 69 - 73 (2007/10/02)
Aldehydes are converted by thionyl chloride and benzotriazole into 1-(1-chloroalyl)benzotriazoles which react with sodium carboxylates to give 1-(benzotriazol-1-yl)alkyl esters. 3. In the alternative route, 3 are prepared by substitution of one of the acetoxy groups in acylals with benzotriazole. The benzotriazolyl moiety in 3 is substituted by an alkyl, an aryl or an alkynyl group upon treatment with an organic reagent in a new versatile synthesis of esters 4.
The Chemistry of N-Substituted Benzotriazoles. Part 2. Reactions of Benzotriazole with Aldehydes and Aldehyde Derivatives. 1-(α-Hydroxyalky)-, 1-(α-Alkoxyalkyl)-, and 1-(α-Acyloxyalkyl)benzotriazoles
Katritzky, Alan R.,Rachwal, Stanislaw,Rachwal, Bogumila
, p. 791 - 798 (2007/10/02)
Benzotriazole reacts readily with a variety of aldehydes to yield crystalline 1:1 adducts characterized by strong hydrogen bonding.Corresponding 1-(α-alkoxyalkyl)benzotriazoles are formed in the presence of alcohols, and 1-(α-acetoxyalkyl) analogues resul
