341979-43-9Relevant academic research and scientific papers
Copper-Catalyzed C(sp2)-H Difluoroalkylation of Aldehyde Derived Hydrazones with Diboron as Reductant
Ke, Miaolin,Song, Qiuling
, p. 3654 - 3664 (2016)
An efficient and general method for C(sp2)-H difluoroalkylation of aldehyde derived hydrazones via a CuII/B2pin2-catalyzed reaction between difluoroalkyl bromides and hydrazones was developed. In this reaction,
α-Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1-(Dialkylamino)-1,2,3-triazoles
Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel
supporting information, p. 6943 - 6948 (2021/02/26)
The one-pot synthesis of a series of sulfonium salts containing transferable diazomethyl groups is described, and the structure of these compounds is elucidated by X-ray crystallography. Under photochemical conditions, reaction of these salts with N,N-dialkyl hydrazones affords 1-(dialkylamino)-1,2,3-triazoles via diazomethyl radical addition to the azomethine carbon followed by intramolecular ring closure. The straightforward transformation of the structures thus obtained into mesoionic carbene–metal complexes is also reported and the donor properties of these new ligands characterized.
Transition-Metal-Free Trifluoromethylation of Aldehyde Derivatives with Sodium Trifluoromethanesulfinate
Tan, Zheng,Zhang, Shiwei,Zhang, Yan,Li, Yunpeng,Ni, Minjie,Feng, Bainian
, p. 9384 - 9399 (2017/09/23)
A metal-free and cost-effective synthetic protocol for the trifluoromethylation of N,N-disubstituted hydrazones with Langlois's reagent (CF3SO2Na) to afford the corresponding functionalized trifluoromethyl ketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a trifluoroalkyl radical may be involved in the reaction. Applications of the methodology in industry will be found and the development of new methods for trifluoromethylation with Langlois's reagent will be continued in our laboratory.
Gold-Catalyzed Highly Selective Photoredox C(sp2)-H Difluoroalkylation and Perfluoroalkylation of Hydrazones
Xie, Jin,Zhang, Tuo,Chen, Fei,Mehrkens, Nina,Rominger, Frank,Rudolph, Matthias,Hashmi, A. Stephen K.
supporting information, p. 2934 - 2938 (2016/02/27)
The first gold-catalyzed photoredox C(sp2)-H difluoroalkylation and perfluoroalkylation of hydrazones with readily available RF-Br reagents is reported. The resulting gem-difluoromethylated and perfluoroalkylated hydrazones are highl
Reaction of the lithio-derivative of methoxyallene with hydrazones. Part 1: Synthesis and transformation of α-allenyl hydrazines
Breuil-Desvergnes, Valérie,Goré, Jacques
, p. 1939 - 1950 (2007/10/03)
The lithio-derivative of methoxyallene reacts with aldehyde hydrazones leading to expected α-allenyl hydrazines when ether is the solvent of the reaction. The yields are good as well as the diastereoselectivity observed in the case of SAMP-hydrazones. These hydrazines are cleanly transformed to N-dialkylamino-3-methoxy-3-pyrrolines when they are reacted with n-BuLi in THF. These compounds are sometimes accompanied by the isomeric 4-methyl azetidines. The N-dialkylamino-3-methoxy-3-pyrrolines are transformed to 3-methoxy-3-pyrrolines by hydrogenolysis of the nitrogen-nitrogen bond, to 3-alkoxy-pyrroles by treatment with a peracid and to 3-amino-pyrroles by acidic migration of the dialkylamino group. In the case of SAMP-hydrazines, the obtained 3-methoxy-3-pyrrolines have a high enantiomeric purity. Lastly, attempts to prepare α-hydrazino-esters (and subsequently α-amino-esters) by ozonolysis of the allenyl moiety failed due to the formation of a methyl glyoxylate.
