54856-82-5Relevant articles and documents
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.
Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology
Rullière, Pauline,Benoit, Guillaume,Allouche, Emmanuelle M. D.,Charette, André B.
, p. 5777 - 5782 (2018/05/14)
Despite the high synthetic potential of nonstabilized diazo compounds, their utilization has always been hampered by stability, toxicity, and safety issues. The present method opens up access to the most reactive nonstabilized diazoalkanes. Among diazo compounds, nonstabilized alkyl diazo compounds are the least represented because of their propensity to degrade during preparation. The continuous flow oxidation process of hydrazones on a silver oxide column afforded an output stream of base- and metal-free pure diazo solution in dichloromethane. Starting from innocuous ketones and aldehydes, this methodology allows the production of a broad range of unprecedented diazoalkanes compounds in excellent yields, while highlighting their synthetic potential and the possibility of safe large-scale diazo production.
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
, 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).