1000587-30-3Relevant articles and documents
Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts
Xiao, Ming-Yang,Chen, Zhen,Zhang, Fa-Guang,Ma, Jun-An
, (2020/03/04)
Here we present a dipolar [3 + 2] cycloaddition transformation of diazoacetates with arenediazonium salts under silver catalysis, thus offering a straightforward approach for the regioselective construction of carboxylic tetrazoles. Several merits are accompanied with this reaction including readily available starting reagents, broad coupling scope, high yields, and friendly reaction conditions. The synthetic value is further showcased by one-pot conversion of commercially available primary arylamines to tetrazoles and successful transformations of the cycloadducts into valuable 5-fluoromethyltetrazoles and an analogue of P2X3 receptor antagonist.
Construction of Difluoromethylated Tetrazoles via Silver-Catalyzed Regioselective [3 + 2] Cycloadditions of Aryl Diazonium Salts
Peng, Xing,Xiao, Ming-Yang,Zeng, Jun-Liang,Zhang, Fa-Guang,Ma, Jun-An
, p. 4808 - 4811 (2019/06/27)
A silver-catalyzed regioselective [3 + 2] cycloaddition reaction of PhSO2CF2CHN2 with aryl diazonium salts is described. This protocol enables the straightforward construction of a novel class of difluoromethylated tetrazoles under mild conditions, tolerates a broad spectrum of functionalities, and is applicable to one-pot operation from commercially available aniline derivatives. The synthetic merit of this method is further demonstrated by the facile preparation of versatile difluoromethylated azoles, including a valuable HCF2-analogue of P2X3 receptor antagonist.
