133349-85-6Relevant academic research and scientific papers
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.
Benzylic C(sp3)-H Functionalization for C-N and C-O Bond Formation via Visible Light Photoredox Catalysis
Pandey, Ganesh,Laha, Ramkrishna,Singh, Deepak
, p. 7161 - 7171 (2016/08/30)
A visible light mediated highly selective benzylic C-H bond functionalization for intermolecular C-N and C-O bond formation is reported. This cross-dehydrogenative coupling reaction demonstrates a straightforward protocol for incorporating the heteroaromatics to the benzylic position. Benzylic oxidation of various alkyl aryls to corresponding carbonyl compounds has also been reported.
Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp3 C-N bond formation under metal-free conditions
Liu, Wenbo,Liu, Chenjiang,Zhang, Yonghong,Sun, Yadong,Abdukadera, Ablimit,Wang, Bin,Li, He,Ma, Xuecheng,Zhang, Zengpeng
, p. 7154 - 7158 (2015/07/01)
The heterocyclic ionic liquid-catalyzed direct oxidative amination of benzylic sp3 C-H bonds via intermolecular sp3 C-N bond formation for the synthesis of N-alkylated azoles under metal-free conditions is reported for the first time. The catalyst 1-butylpyridinium iodide can be recycled and reused with similar efficacies for at least eight cycles.
Metal-free, highly efficient organocatalytic amination of benzylic C-H bonds
Xue, Qicai,Xie, Jin,Li, Huamin,Cheng, Yixiang,Zhu, Chengjian
supporting information, p. 3700 - 3702 (2013/05/09)
A new synthetic approach toward direct C-N bond formation through sp 3 C-H activation has been developed under metal-free conditions. Both primary and secondary benzylic C-H substrates could react smoothly with various amines to give only mono-amination products with good to excellent yields. The Royal Society of Chemistry 2013.
Reactivity of AllylSmBr/HMPA: Facile Synthesis of 3-Aryl-1,2,4- benzotriazines
Yin, Ruifeng,Zhou, Liejin,Liu, Huili,Mao, Hui,Lue, Xin,Wang, Xiaoxia
, p. 143 - 148 (2013/08/24)
3-Aryl-1,2,4-benzotriazines were conveniently prepared in moderate to good yields from 1,l-bis(benzotriazol-1-yl)methylarenes with allylsamarium bromide/hexamethylphosphramide (allylSmBr/HMPA). Preliminary results indicate that HMPA may enhance the reduci
Acidic-functionalized ionic liquid as an efficient, green, and metal-free catalyst for benzylation of sulfur, nitrogen, and carbon nucleophiles to benzylic alcohols
Chu, Xue-Qiang,Jiang, Ran,Fang, Yi,Gu, Zheng-Yang,Meng, Hua,Wang, Shun-Yi,Ji, Shun-Jun
supporting information, p. 1166 - 1174 (2013/02/25)
A series of HSO4- functionalized ILs was synthesized and used as efficient, green, and metal-free catalysts for benzylation. Notably, the catalytic system has wide substrate scopes and the ionic liquid catalysts were applied to investigate three different types of nucleophiles to give the desired benzylation products with moderate to excellent yields.
In(OTf)3 catalyzed N-benzylation of amines utilizing benzyl alcohols in water
Yang, Jin-Ming,Jiang, Ran,Wu, Lin,Xu, Xiao-Ping,Wang, Shun-Yi,Ji, Shun-Jun
, p. 7988 - 7994 (2013/08/23)
An In(OTf)3-catalyzed N-benzylation of amines utilizing benzyl alcohols through direct C-O bond activation has been reported. The reaction was performed in water without any base, additive, ligand or inert gas protection to afford the chem-selective mono- or bis-alkylated aromatic amines in good to excellent yields.
Oxidation of 1-[(Aryl)(phenylseleno)methyl]-, 1-[(Aryl)(arylthio)-(phenylseleno)methyl]-, and 1-[(Aryl)(diphenylseleno)-methyl]benzotriazoles with m-Chloroperbenzoic Acid
Kang, Yoon Ho,Kim, Kyongtae
, p. 1741 - 1752 (2007/10/03)
During the last decade, benzotriazole (1) has received much attention as an excellent synthetic auxiliary [1]. Recently Katritzky, et al. [2] studied the oxidation of 1-(phenylthiomethyl)benzotriazole (2a) and 1-(2-phenyl-1-phenylthioethyl)benzotriazole (2b) and obtained their sulfones and sulfoxides by treatment with m-chloroperbenzoic acid (m-CPBA) and sodium periodate, respectively. No compounds derived from a heterolytic cleavage between the α-carbon and the N-1 atoms of the foregoing compounds were isolated.
N-benzotriazoles: Preparation and Use in Synthesis
Katritzky, Alan R.,Lan, Xiangfu,Lam, Jamshed N.
, p. 1819 - 1826 (2007/10/02)
Methoxybenzenes and -naphthalenes are benzotriazolylmethylated in the para-position or if this is blocked in an ortho-position.The methylene groups in the products are readily substituted by electrophiles via the lithiated derivatives.Displacement ot the benzotriazole group can be effected by organometallic reagents or by electron-rich benzoid compounds to afford a versatile method for the synthesis of substituted aryl ethers.Key Words: Lithiation/ Grignard reaction/ Condensation/ Aryl ethers/ Diarylmethanes
