18315-79-2Relevant academic research and scientific papers
Highly stereoselective nitration of chalcone derivatives with nitric oxide
Li, Rui,Liu, Zhongquan,Zhou, Yulu,Wu, Longmin
, p. 1367 - 1368 (2006)
A novel nitration of chalcone derivatives with nitric oxide affords E-α-nitropropenones exclusively in good yield. The reaction is most likely initiated by electrophilic addition of nitric dioxide to the C=C double bond at the α-position. Georg Thieme Ver
α-Nitro-α,β-Unsaturated Ketones: An Electrophilic Acyl Transfer Reagent in Catalytic Asymmetric Friedel-Crafts and Michael Reactions
Parida, Chandrakanta,Maity, Rajendra,Chandra Sahoo, Subas,Chandra Pan, Subhas
supporting information, p. 6700 - 6704 (2019/09/07)
Herein, we introduce α-nitro-α,β-unsaturated ketones as efficient electrophilic acyl transfer reagents, and they were employed in Friedel-Crafts as well as in Michael reactions. The desired acyl transfer products of these reactions were obtained in high yields with high to excellent enantioselectivities with t-leucine-derived squaramide catalyst under mild reaction conditions. Few applications including a synthesis of the isoxazoline motif have been demonstrated.
Synthetic Diversity from a Versatile and Radical Nitrating Reagent
Zhang, Kun,Jelier, Benson,Passera, Alessandro,Jeschke, Gunnar,Katayev, Dmitry
supporting information, p. 12929 - 12939 (2019/09/17)
We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.
Preparation, reduction chimique et electrochimique d'α-nitrostyrylcetones - synthese d'heterocycles azotes
Marcot, Bernard,Rabaron, Alain,Viel, Claude,Bellec, Christian,Deswarte, Stephane,Maitte, Pierre
, p. 1224 - 1234 (2007/10/02)
Nitration of styryl ketones with nitrogen peroxide leads to the corresponding α-nitroethylenic ketones in good yield.However, the presence of methoxy groups involves a nitration on the aromatic nucleus.LiAlH4 reduction of α-nitrostyrylketones yields the c
