15965-37-4Relevant academic research and scientific papers
Another way to the synthesis of 1,2,3-triazoles
Xu, Beihua,Hu, Yongzhou
, p. 1217 - 1222 (2013)
The reactions of α-bromoacetophenones with methylhydrazine in refluxing acetic acid generated 2-methyl-4-aryl-2H-[1,2,3]triazoles in good yields. The method was developed by the reactions of α-bromoacetophenones with phenylhydrazines in the presence of cu
Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air
Ji, Jian,Guan, Cong,Wei, Qinghua,Chen, Xuwen,Zhao, Yun,Liu, Shunying
supporting information, p. 132 - 136 (2022/01/04)
We developed a highly regioselective base-induced synthesis of N2-substituted 1,2,3-triazoles from N-sulfonyl-1,2,3-triazoles and alkyl bromides/alkyl iodides at room temperature. We propose an SN2-like mechanistic pathway to explain the high N2-regioselectivity. The protocol features a broad substrate scope and generates products in good to excellent yields (72–90%).
Decarboxylative sp 3 C-N coupling via dual copper and photoredox catalysis
Liang, Yufan,Zhang, Xiaheng,MacMillan, David W. C.
, p. 83 - 88 (2018/07/24)
Over the past three decades, considerable progress has been made in the development of methods to construct sp 2 carbon-nitrogen (C-N) bonds using palladium, copper or nickel catalysis 1,2 . However, the incorporation of alkyl substrates to form sp 3 C-N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform from which to address this challenge. This cross-coupling system uses naturally abundant alkyl carboxylic acids and commercially available nitrogen nucleophiles as coupling partners. It is applicable to a wide variety of primary, secondary and tertiary alkyl carboxylic acids (through iodonium activation), as well as a vast array of nitrogen nucleophiles: nitrogen heterocycles, amides, sulfonamides and anilines can undergo C-N coupling to provide N-alkyl products in good to excellent efficiency, at room temperature and on short timescales (five minutes to one hour). We demonstrate that this C-N coupling protocol proceeds with high regioselectivity using substrates that contain several amine groups, and can also be applied to complex drug molecules, enabling the rapid construction of molecular complexity and the late-stage functionalization of bioactive pharmaceuticals.
Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition
R?hrig, Ute F.,Majjigapu, Somi Reddy,Grosdidier, Aurélien,Bron, Sylvian,Stroobant, Vincent,Pilotte, Luc,Colau, Didier,Vogel, Pierre,Van Den Eynde, Beno?t J.,Zoete, Vincent,Michielin, Olivier
, p. 5270 - 5290 (2012/08/28)
Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.
A facile synthesis of 2-methyl-1,2,3-triazoles
Xu, Beihua,Hu, Yongzhou
, p. 96 - 97 (2007/10/03)
Reaction of α-bromoacetophenone bearing various substituents on the benzene rings with methylhydrazine in refluxing acetic acid afforded 2-methyl-4-phenyl-1,2,3-triazoles. The relation between the substituents and the yields is briefly discussed.
OXIDATION OF 2,5-DIHYDRO-1,2,3-TRIAZINES BY m-CHLOROPERBENZOIC ACID
Itoh, Takashi,Ohsawa, Akio,Kaihoh, Terumitsu,Igeta, Hiroshi
, p. 33 - 36 (2007/10/02)
2,5-Dihydro-1,2,3-triazines were oxidized by m-chloroperbenzoic acid to give only 1,2,3-triazine 2-oxides, while the oxidation of 1,2,3-triazines yielded the mixtures of 1- and 2-oxides.In case of adopting 2-methyl-2,5-dihydro-1,2,3-triazines as starting materials, 2-methyltriazoles and 2,5-dihydro-5-oxo-1,2,3-triazine were obtained.
