32787-75-0Relevant academic research and scientific papers
Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides
Janhsen, Benjamin,Studer, Armido
, p. 11703 - 11710 (2017/11/24)
Radical trifluoromethylation of aryl N,N-dimethyl hydrazones using TBAI as an initiator and Togni's reagent as a trifluoromethyl radical source is described. Cascades proceed via electron-catalysis; this approach is generally more applicable to hydrazone perfluoroalkylation using perfluoroalkyl iodides as the radical precursors in combination with a base under visible-light initiation.
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
New types of reactivity of α,β-unsaturated N,N- dimethylhydrazones: Chemodivergent diastereoselective synthesis of functionalized tetrahydroquinolines and hexahydropyrrolo[3,2-b]indoles
Sridharan, Vellaisamy,Ribelles, Pascual,Estevez, Veronica,Villacampa, Mercedes,Ramos, M. Teresa,Perumal, Paramasivan T.,Menendez, J. Carlos
, p. 5056 - 5063 (2012/05/20)
The indium trichloride-catalyzed reaction between aromatic imines and α,β-unsaturated N,N-dimethylhydrazones in acetonitrile afforded 1,2,3,4-tetrahydroquinolines bearing a hydrazone function at C4 through a one-pot diastereoselective domino process that involves the formation of two C-C bonds and the controlled generation of two stereocenters, one of which is quaternary. This reaction constitutes the first example of an α,β-unsaturated dimethylhydrazone that behaves as a dienophile in a hetero Diels-Alder reaction. The related reaction between anilines, aromatic aldehydes, and methacrolein dimethylhydrazone in CHCl3 with BF 3·Et2O as catalyst afforded polysubstituted 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles as major products through a fully diastereoselective ABB′C four-component domino process that generates two cycles, three stereocenters, two C-C bonds, and two C-N bonds in a single operation. Copyright
A 'one-pot' procedure for the oxidative conversion of alkyl halides and tosylates to N,N-dimethylhydrazones
Barrett,Kerr
, p. 1673 - 1675 (2007/10/03)
The treatment of a solution of an alkyl halide with sodium azide results in the formation of a solution of the alkyl azide, which upon filtration to remove the sodium halide, is treated with N,N-dimethyl hydrazine and catalytic FeCl3.6H2O under refluxing conditions. The result is a one pot conversion of an alkyl halide to an N,N-dimethyl hydrazone, a net oxidation of the halogen-bearing carbon.
Conversion of Aldehydes into Nitriles via Oxidation of Their Dimethylhydrazones
Said, Samy Bayomy,Skarzewski, Jacek,Mlochowski, Jacek
, p. 223 - 224 (2007/10/02)
The 3-chloroperoxybenzoic acid oxidation of dimethylhydrazones of aromatic aldehydes gives the corresponding nitriles in good yields.Two further examples of the same oxidative transformation of cinnamaldehyde and of hexanal are also given.Except for hexanal hydrazone, all other aldehyde hydrazones can also be efficiently converted into nitriles by treatment with methanolic 30percent hydrogen peroxide in the presence of catalytic amounts of selenium dioxide or, preferentially, 2-nitrobenzeneseleninic acid.
