14371-13-2Relevant 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
Hydrazone as the directing group for Ir-catalyzed arene diborylations and sequential functionalizations
Ros, Abel,Lopez-Rodriguez, Rocio,Estepa, Beatriz,Alvarez, Eleuterio,Fernandez, Rosario,Lassaletta, Jose M.
supporting information; experimental part, p. 4573 - 4576 (2012/04/23)
The use of hemilabile pyridine-hydrazone N,N-ligands allows the highly selective Ir-catalyzed ortho,ortho'-directed diborylation of aromatic N,N-dimethylhydrazones in near-quantitative yields. One-pot sequential Suzuki-Miyaura cross-coupling with different aryl bromides provides a short entry to unsymmetrically substituted 2,6-diarylbenzaldehyde derivatives.
Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes
Dubrovskiy, Anton V.,Larock, Richard C.
, p. 11232 - 11256 (2013/02/23)
A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
Use of hemilabile N,N ligands in nitrogen-directed iridium-catalyzed borylations of arenes
Ros, Abel,Estepa, Beatriz,Lopez-Rodriguez, Rocio,Alvarez, Eleuterio,Fernandez, Rosario,Lassaletta, Jose M.
supporting information; experimental part, p. 11724 - 11728 (2012/02/14)
The hemilabile character of 2-pyridyl carbaldehyde hydrazones as N,N bidentate ligands is key to performing regioselective IrIII-catalyzed ortho borylations of 2-aryl pyridines(isoquinolines) and aromatic N,N-dimethylhydrazones (see scheme; pin=pinacol, Bn=benzyl). Internal "ate" complexes or products free from N-B interactions are formed depending on the steric properties of the substrates. Copyright
Synthesis of o -(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes
Dubrovskiy, Anton V.,Larock, Richard C.
supporting information; experimental part, p. 4136 - 4139 (2011/10/12)
A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones and acridones has been developed starting from readily available 1,1-dimethylhydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
From aldehydes to nitriles, a general and high yielding transformation using HOF·CH3CN complex
Carmeli, Mira,Shefer, Neta,Rozen, Shlomo
, p. 8969 - 8972 (2007/10/03)
N,N-Dimethylhydrazones of aldehydes undergo a rapid oxidative cleavage to form nitriles in very high yields on reaction with HOF·CH3CN under mild conditions. The reaction is chemoselective and proceeds rapidly without racemization. The nitriles were resistant to further oxidation, even when a large excess of the reagent was employed.
Synthesis and reactions of (1E, 2Z)-2-N,N-dialkylhydrazono-2-phenylethanal N,N-dimethylhydrazones
Brehme, Rainer,Reck, Guenter,Schulz, Burkhard,Radeglia, Reiner
, p. 1620 - 1625 (2007/10/03)
(1E,2Z)-2-N,N-Dialkylhydrazono-2-phenylethanal N,N-dimethylhydrazones 3a-e were synthesised by the reaction of 1,4,5-triazapentadienium salts 2 with N,N-dimethylhydrazine. The compounds 3a and 3d did not react with tosyl isocyanate in an electrophilic substitution reaction at the azomethine C-1 as aza-enamines, but they reacted at room temperature in benzene in a 1,4-dipolar cycloaddition to yield 1,3,5-triazinan-2,4-diones 5a and 5d, whereas at 70°C octahydroimidazoimidazol-2,5-dione 6a was formed via criss-cross addition reaction. With dimethyl sulfate in DMF, 3a was transformed into the trimethylhydrazonium salts 7a and 8a, isolated as co-crystallised perchlorates (molar ratio 1:1).
A novel, one-pot synthesis of α-C-cyanohydrazines in the presence of lithium perchlorate/diethylether solution (5.0 M)
Heydari, Akbar,Baharfar, Robabe,Rezaie, Mohsen,Aslanzadeh, Saied M.
, p. 368 - 369 (2007/10/03)
Condensation of N,N-dimethylhydrazine, an aldehyde in lithium perchlorate/diethylether solution (5.0 M) gave N,N-dimethylhydrazone, which were treated with trimethylsilylcyanide to afford α-C-cyanohydrazine. These compounds are important precursors of nitrogen-substituted reagents.
