6299-90-7Relevant academic research and scientific papers
Facile synthesis of benzotriazines and indoles by ring-scissions of α- Benzotriazol-1-yl hydrazones
Katritzky, Alan R.,Wang, Jin,Karodia, Nazira,Li, Jianqing
, p. 3963 - 3976 (1997)
α-(Benzotriazol-1-yl)hydrazones 2a-d and 13a-c were prepared by refluxing the corresponding α-(benzotriazol-1-yl)ketones with p-tosyl hydrazide or benzenesulfonyl hydrazide. Treatment of 2a-b with n-butyllithium in the presence of TMEDA gave benzotriazines 6a-b, while lithiation of 13a-c resulted in indole derivatives 16a-c, depending on the structure of the hydrazones.
Synthesis of 1,2,4-Benzotriazines via Copper(I) Iodide/1 H -Pyrrole-2-carboxylic Acid Catalyzed Coupling of o -Haloacetanilides and N -Boc Hydrazine
Zhou, Yijun,Zhang, Zhigao,Jiang, Yongwen,Pan, Xianhua,Ma, Dawei
, p. 1586 - 1590 (2015)
Coupling of o-haloacetanilides and N-Boc hydrazine proceeded at room temperature under the catalysis of CuI/1H-pyrrole-2-carboxylic acid. The coupling products underwent oxidation to afford the azo compounds, which were subjected to deprotection with TFA
Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine
Wu, Weiping,Fan, Shuaixin,Li, Tielei,Fang, Lili,Chu, Benfa,Zhu, Jin
, p. 5652 - 5657 (2021/08/01)
Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.
Aryl-Nickel-Catalyzed Benzylic Dehydrogenation of Electron-Deficient Heteroarenes
Zhang, Pengpeng,Huang, David,Newhouse, Timothy R.
supporting information, p. 1757 - 1762 (2020/02/04)
This manuscript describes the first practical benzylic dehydrogenation of electron-deficient heteroarenes, including pyridines, pyrazines, pyrimidines, pyridazines, and triazines. This transformation allows for the efficient benzylic oxidation of heteroarenes to afford heterocyclic styrenes by the action of nickel catalysis paired with an unconventional bromothiophene oxidant.
Palladium-Catalyzed ortho -Monoacylation of Arenes with Aldehydes via 1,2,4-Benzotriazine-Directed C-H Bond Activation
Cui, Bingcun,Hu, Gang,Huang, Guosheng,Jin, Shaofen,Liu, Jin,Liu, Tingting,Ni, Dongmei,Yu, Xin,Zhou, Yingxing
supporting information, p. 1407 - 1416 (2020/04/27)
An efficient palladium-catalyzed C-H bond functionalization/ ortho -monoacylation reaction of 3-aryl-1,2,4-benzotriazines with (hetero)aryl or alkyl aldehydes has been developed, which offers a facile and alternative strategy for direct modification and further diversification of 3-aryl-1,2,4-benzotriazines. Bioactive 1,2,4-benzotriazine has been employed as a novel directing group for the palladium-catalyzed regioselective monoacylation of sp 2 C-H bond protocol with broad substrate scope and good functional group tolerance.
C(3) Functional Derivatives of the Blatter Radical
Pomik?o, Dominika,Bodzioch, Agnieszka,Pietrzak, Anna,Kaszyński, Piotr
supporting information, p. 6995 - 6999 (2019/09/30)
A series of 3-substituted 1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yls 1 was prepared by addition of PhLi to 3-substituted benzo[e][1,2,4]triazines 2 followed by aerial oxidation. The scope of the C(3) substituents in the reaction was investigated, an
3-Substituted Benzo[ e][1,2,4]triazines: Synthesis and Electronic Effects of the C(3) Substituent
Bodzioch, Agnieszka,Pomik?o, Dominika,Celeda, Ma?gorzata,Pietrzak, Anna,Kaszyński, Piotr
, p. 6377 - 6394 (2019/05/24)
A series of 19 structurally diverse C(3)-substituted derivatives of benzo[e][1,2,4]triazine were synthesized from 3-chloro- (1c) and 3-iodobenzo[e][1,2,4]triazine (1d) obtained in three steps from 2-nitroaniline in 37-55% yields. Nucleophilic aromatic substitution and metal-catalyzed (Pd, Cu) reactions led to functional derivatives that include alkyl (C5H11), (het)aryl (Ph, 2-thienyl, ferrocenyl), ArCC, amine (NHPh and morpholine), PO(OEt)2, sulfanyl (SBu-t), alkoxide (OEt, OMe), and CN. The synthesis of C(3)-CF3 derivative 1g via the Ruppert reaction with 1d and its 1-oxide analogue 2d led to the substitution followed by formal addition of HCF3 to the C?N bond. Pd-catalyzed carbonylation reactions of 1d and 2d did not give the corresponding C(3)-carboxylic acids. Therefore, acid 1f was obtained through hydrolysis of the CN. The substituent effect on the electronic structure of the benzo[e][1,2,4]triazine ring was investigated by spectroscopic methods (UV-vis and NMR) augmented with density functional theory calculations. Results show significant effect of the C(3) substituent on the (1) transition energy and good correlation of the 1H NMR chemical shift with the substituent constant σp. Molecular and crystal structures of six derivatives were established with the single-crystal X-ray diffraction method, and the substituent impact on the molecular geometry was investigated.
Access to 1,4-Dihydrobenzo[e][1,2,4]triazin-4-yl Derivatives
Constantinides, Christos P.,Obijalska, Emilia,Kaszyński, Piotr
supporting information, p. 916 - 919 (2016/03/15)
A simple, one-pot method for the preparation of 1-aryl-3-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radicals by addition of aryllithium to the readily available 3-phenylbenzo[e][1,2,4]triazine followed by aerial oxidation is described. The intermediate
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
Copper-catalyzed domino reaction of 2-haloanilines with hydrazides: A new route for the synthesis of benzo[e][1,2,4]triazine derivatives
Guo, Han,Liu, Jin,Wang, Xianxue,Huang, Guosheng
supporting information; experimental part, p. 903 - 906 (2012/05/20)
A copper-catalyzed domino reaction for the synthesis of benzo[e][1,2,4]triazine derivatives has been developed using readily available substituted 2-haloanilines and hydrazides as the starting materials. The procedure of the present method is mild, facile
