4106-18-7Relevant academic research and scientific papers
Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
supporting information, p. 58 - 63 (2021/12/27)
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
Organolithium-Mediated Postfunctionalization of Thiazolo[3,2- c][1,3,5,2]oxadiazaborinine Fluorescent Dyes
Ceborska, Magdalena,Danyliv, Yan,Grazulevicius, Juozas V.,Hladka, Iryna,Luboradzki, Roman,Potopnyk, Mykhaylo A.,Volyniuk, Dmytro
, p. 6060 - 6072 (2020/05/22)
An effective method for transition-metal-free postfunctionalization of thiazolo[3,2-c][1,3,5,2]oxadiazaborinine dyes via direct lithiation of the 1,3-thiazole ring was developed. The reaction allows valuable regioselective C-H modification of these N,O-ch
Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines
Faggyas, Réka J.,Sloan, Nikki L.,Buijs, Ned,Sutherland, Andrew
, p. 5344 - 5353 (2019/05/21)
An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.
Hypervalent Iodine Mediated Sulfonamide Synthesis
Poeira, Diogo L.,Macara, Jo?o,Faustino, Hélio,Coelho, Jaime A. S.,Gois, Pedro M. P.,Marques, M. Manuel B.
supporting information, p. 2695 - 2701 (2019/04/08)
A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.
Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature
Azeez, Sadaf,Chaudhary, Priyanka,Sureshbabu, Popuri,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information, p. 6902 - 6907 (2018/10/02)
A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.
Convenient sulfonylation of imidazoles and triazoles using NFSI
Jie, Kun,Wang, Yufeng,Huang, Ling,Guo, Shengmei,Cai, Hu
, p. 465 - 471 (2018/06/18)
A protocol for the synthesis of N-sulfonyl imidazoles and triazoles has been achieved using N-Fluorobenzenesulfonimide as a sulfonyl source. This reaction proceeded well in the absence of strong bases and catalysts, providing a convenient alternative method for the preparation of N-sulfonyl imidazoles as well as triazoles.
Sodium hydrogen exchanger inhibitory activity of benzotriazole derivatives
Singh, Dhandeep,Silakari, Om
, p. 183 - 189 (2016/10/25)
Series of benzotriazole derivatives were synthesized and evaluated for their Sodium hydrogen exchanger-1 inhibitory potential. All compounds inhibit Sodium hydrogen exchanger-1 in the in-vitro platelet swelling assay. This is perhaps the first report of NHE-1 inhibitory activity of benzotriazole. The 1-alkyl benzotriazole derivatives were found to be more active than the 2-alkyl isomers. The activity increases with increase in chain length of alkyl moiety. Potency increased from that of benzotriazole (IC50= 192.68 μM) to heptyl derivative (compound 13; IC50= 59.23 μM). Introduction of electronegative oxygen atom further increased potency as shown by the benzoyl (compound 16, IC50= 51.57 μM) and sulfonyl groups (compound 17, IC50= 50.89 μM; compound 18, IC50= 49.95 μM).
Solvent free, highly chemoselective N and O-acylation on silica and silica magnesium oxide: A recyclable solid surface
Ghosh, Pranab,Mandal, Amitava
, p. 261 - 268 (2012/10/29)
Silica or silica/magnesium oxide mixed surface mediates the N and O-acylation, benzoylation or sulfonylation of hosts of substrates under solvent free conditions at ambient temperature with high chemoselectivity.
Sulfonyl derivatives of benzotriazole: Part 1. A novel approach to the activation of carboxylic acids
Katritzky, Alan R.,Shobana,Pernak, Juliusz,Afridi,Fan, Wei-Qiang
, p. 7817 - 7822 (2007/10/02)
1-Acylbenzotriazoles (8, R = Me, Et, n-Bu and Ph) are prepared in good yields by fusion of benzotriazole and acid chlorides at 80 - 100°C. In cases when the corresponding acid chlorides are not available, 1-acylbenzotriazoles are conveniently available from 1-(1-methanesulfonyl) benzotriazole and the respective carboxylic acids as illustrated by the preparation of 2-, 3-, and 4-pyridoyl-, 2-pyrrolylcarbonyl- and 2-furoyl-benzotriazole in yields of 80 - 95%. Preparations of two sulfonyl derivatives of benzotriazole are also described.
