832-81-5Relevant articles and documents
Synthesis and structural characterization of arene d6 metal complexes of sulfonohydrazone and triazolo ligands: High potency of triazolo derivatives towards DNA binding
Shadap, Lathewdeipor,Joshi, Nidhi,Poluri, Krishna Mohan,Kollipara, Mohan Rao,Kaminsky, Werner
, p. 302 - 312 (2018)
Complexation of [(p-cymene)RuCl2]2 and [Cp?MCl2]2 (M = Rh/Ir) with chelating ligand 4-methylbenzenesulfonohydrazone ligands (L1 and L3) resulted in the formation of mononuclear cationic complexes having PF6
Transannulation of Pyridotriazoles with Naphthoquinones and Indoles: Synthesis of Benzo[f]Pyrido[1,2-a]Indoles and Indolizino[3,2-b]indoles
Rawat, Deepa,Adimurthy, Subbarayappa
, p. 71 - 76 (2021/10/29)
Ruthenium catalysed denitrogenative transannulation of pyridotriazoles with naphthoquinones provided the transannulated benzo[f]pyrido[1,2-a]indoles derivatives in good to excellent yields. While pyridotriazoles with indoles in presence of PivOH and oxone yield indolizino[3,2-b]indoles under metal-free conditions. Quinone annulation proceeds through ruthenium-carbenoid intermediate while indole annulation may proceed via a diazo-pyridinium intermediate. Control experiments suggest that both the transformations follow the ionic mechanism. (Figure presented.).
Nitrous oxide as a diazo transfer reagent: The synthesis of triazolopyridines
Landman, Iris R.,Fadaei-Tirani, Farzaneh,Severin, Kay
supporting information, p. 11537 - 11540 (2021/11/16)
Nitrous oxide is a potential diazo transfer reagent, but its applications in organic chemistry are scarce. Here, we show that triazolopyridines and triazoloquinolines are formed in the reactions of metallated 2-alkylpyridines or 2-alkylquinolines with N2O. The reactions can be performed under mild conditions and give synthetically interesting triazoles in moderate to good yields.
Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones
Huang, Xiang,Chen, Xing,Xie, Haisheng,Tan, Zheng,Jiang, Huanfeng,Zeng, Wei
supporting information, p. 6784 - 6788 (2021/09/08)
A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.
Method for synthesizing [1,2,3]triazole[1,5-a]pyridines compound through non-catalyst N-N coupling reaction
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Paragraph 0032-0037; 0048-0052; 0063-0065, (2019/04/04)
The invention relates to a method for synthesizing [1,2,3]triazole[1,5-a]pyridines compound through non-catalyst N-N coupling reaction. The invention discloses an efficient method for synthesizing a product at one step without using a catalyst under a mild condition from a 2-pyridylamine compound and nitroso tert-butyl ester as a mild nitrogen atom source. The method is free from the catalyst, thereaction step is reduced, the condition is extremely mild, the efficiency is high, and the later modification can be performed on the biological active molecular, thereby facilitating the industrialproduction of [1,2,3]triazole[1,5-a]pyridines compound.
Recyclable Heterogeneous Copper(II)-Catalyzed Oxidative Cyclization of 2-Pyridine Ketone Hydrazones towards [1,2,3]Triazolo[1,5-a]pyridines
Cai, Mingzhong,Jiang, Gan,Lin, Yang,Zhao, Hong
, p. 4487 - 4497 (2019/11/21)
The heterogeneous copper(II)-catalyzed oxidative cyclization of 2-pyridine ketone hydrazones was achieved in ethyl acetate at room temperature in the presence of an MCM-41-anchored bidentate 2-aminoethylamino copper(II) catalyst [MCM-41-2N-Cu(OAc) 2
TBAB-Catalyzed Csp3–N Bond Formation by Coupling Pyridotriazoles with Anilines: A New Route to (2-Pyridyl)alkylamines
Lamaa, Diana,Lin, Hsin-Ping,Bzeih, Tourin,Retailleau, Pascal,Alami, Mouad,Hamze, Abdallah
supporting information, p. 2602 - 2611 (2019/04/16)
A new metal-free procedure allowing Csp3–N bond formation through coupling of pyridotriazoles and weakly nucleophilic anilines has been developed. This sustainable reaction shows high tolerance towards functional groups (ketones, free alcohols) leading to 2-picolylamine derivatives. The key to our success is the use of a catalytic amount of TBAB and water as a co-solvent leading to the formation of pyridylalkylamine derivatives. As this coupling tolerates the presence of Csp2–Br bond on both partners of the reaction, we performed a sequential one-pot reaction between functionalized triazolopyridines and anilines followed by a second coupling with N-tosylhydrazones leading to the formation of Csp3–N and Csp2–Csp2 bonds.
Indium-catalyzed denitrogenative transannulation of pyridotriazoles: Synthesis of pyrido[1,2- A[indoles
Rawat, Deepa,Ravi, Chitrakar,Joshi, Abhisek,Suresh, Eringathodi,Jana, Kalyanashis,Ganguly, Bishwajit,Adimurthy, Subbarayappa
supporting information, p. 2043 - 2047 (2019/03/26)
Pyrido[1,2-a]indoles are known for medicinally and pharmaceutically important compounds; however, the efficient synthetic routes are scarce in the literature. We report herein a convenient and efficient route to synthesize these molecules through indium-catalyzed transannulation of pyridotriazoles with arenes. A library of compounds have been synthesized employing the method developed with various substituted pyrido[1,2-a]indole derivatives in moderate to good yields. The density functional theory study using SMDDCB-M06/6-31++G(d,p)/LANL2DZ//B3LYP/6-31G(d)/LANL2DZ method suggests that the reactions proceed via indium-carbenoid complex.
Palladium-Catalyzed Divergent Arylation with Triazolopyridines: One-Pot Synthesis of 6-Aryl-2-α-styrylpyridines
Moon, Youngtaek,Kwon, Soonhyung,Kang, Dahye,Im, Honggu,Hong, Sungwoo
supporting information, p. 958 - 964 (2016/04/05)
We have developed a new strategy for palladium-catalyzed arylation reactions with triazolopyridines, wherein two different chemical transformations (C-3 vs. C-7) are observed by differentiating the substrates using different bases. The reactive palladium carbenoids were directly generated from triazolopyridines and underwent denitrogenative arylations with aryl bromides. Intriguingly, when potassium carbonate was replaced with potassium tert-butoxide, direct C-H arylation occurred at the most acidic position (C-7). Moreover, two different catalytic arylation events were successfully performed in a one-pot sequence, providing a convenient access to 6-aryl-2-α-styrylpyridines.
Facile one-pot synthesis of [1,2,3]triazolo[1,5-a]pyridines from 2-acylpyridines by copper(II)-catalyzed oxidative N-N bond formation
Hirayama, Tasuku,Ueda, Satoshi,Okada, Takahiro,Tsurue, Norihiko,Okuda, Kensuke,Nagasawa, Hideko
supporting information, p. 4156 - 4162 (2014/04/17)
An efficient and simple method for the synthesis of various [1,2,3]triazolo[1,5-a]pyridines has been established. The method involves a copper(II)-catalyzed oxidative N-N bond formation that uses atmospheric oxygen as the terminal oxidant following hydrazonation in one pot. The use of ethyl acetate as the solvent dramatically promotes the oxidative N-N bond-formation reaction and enables the application of oxidative cyclization in the efficient one-pot reaction. A mechanism for the reaction was proposed on the basis of the results of a spectroscopic study. In the same pot: [1,2,3]Triazolo[1,5-a] pyridines are synthesized from the corresponding 2-acylpyridines by a one-pot method, consisting of hydrazonation followed by oxidative cyclization through copper(II)-catalyzed N-N bond formation (see scheme).
