98203-62-4Relevant academic research and scientific papers
Catalyst-Free Regioselective [3+2] Cycloadditions of α,β-unsaturated N-arylnitrones with Alkenes to Access Functionalized Isoxazolidines: A DFT Study
Ghosh, Arnab,Mane, Manoj V.,Rode, Haridas B.,Patil, Siddappa A.,Sridhar, Balasubramanian,Dateer, Ramesh B.
, p. 899 - 903 (2020/03/03)
The catalyst-free regioselective [3+2]-cycloaddition of α,β-unsaturated N-arylnitrones with alkenes are developed. The series of synthetically important functionalized isoxazolidines are prepared in good to excellent yields by step economic pathway under ligand and transition-metal-free conditions. The regioselective cycloaddition pathway supported by control experiment and computational study.
One-pot synthesis of nitrones from nitro compounds by in situ trapping of arylhydroxylamines
Kazemi, Foad,Ramdar, Moosa,Tavana, Bahram,Davarpanah, Jamal
, p. 1101 - 1107 (2017/05/10)
Abstract: Highly efficient, convenient, simple procedure and a highly chemoselective method has been described for the conversion of nitroarenes to their corresponding nitrone derivatives by employing SnCl2·2H2O and Na2CO3 in the grinding apparatus in solvent-free conditions. Biaryl nitrones can be achieved via the condensation of an aldehyde with an unstable arylhydroxylamine which is prepared in situ through the reduction of the corresponding nitro aromatic compound. Interestingly, the slow and nonselective reduction of nitroarene to arylhydroxylamine step was directed with the condensation of in situ-prepared arylhydroxylamine with aromatic aldehyde (second step). Moreover, this protocol was successfully used for preparation of valuable dinitrones from dialdehyde and nitro aromatic compounds. For dinitrone preparation, dialdehyde compounds were first synthesized by the reaction of salicylaldehyde and glycol derivatives. Then, dialdehydes were reacted with reduced nitro compounds in optimal conditions that we used for synthesis of biaryl nitrones. Graphical Abstract: [Figure not available: see fulltext.].
Rhodium(III)-Catalyzed Redox-Neutral C-H Annulation of Arylnitrones and Alkynes for the Synthesis of Indole Derivatives
Zhou, Zhi,Liu, Guixia,Chen, Yan,Lu, Xiyan
supporting information, p. 2944 - 2950 (2015/09/28)
By using a nitrone as the oxidizing directing group, a mild, practical and efficient rhodium(III)-catalyzed C-H functionalization for the synthesis of indole derivatives has been developed. This reaction obviates the need for an external oxidant and shows good functional group tolerance. The employment of a sterically hindered Mes group on the carbon center of the nitrone is crucial to produce indoles in high yield.
Synthesis of N-styrenyl amidines from α,β-unsaturated nitrones and isocyanates through CO2 elimination and styrenyl migration
Mo, Dong-Liang,Pecak, Wiktoria H.,Zhao, Meng,Wink, Donald J.,Anderson, Laura L.
supporting information, p. 3696 - 3699 (2014/08/05)
A mild, metal-free, and modular route for the preparation of N-styrenyl amidines from N-aryl-α,β-unsaturated nitrones and isocyanates has been developed that accesses an initial oxadiazolidinone intermediate that can undergo CO2 elimination and styrenyl migration. The use of a migration event to install N-styrenyl amidine substituents circumvents a limitation of traditional Pinner-type methods for amidine synthesis that require the use of amine nucleophiles. The modularity of the nitrone and isocyanate reagents provides access to a variety of differentially substituted N-styrenyl amidines. The scope and tolerance of the method are presented, and preliminary mechanistic data for the transformation are discussed.
Solvent-Controlled Bifurcated Cascade Process for the Selective Preparation of Dihydrocarbazoles or Dihydropyridoindoles
Mo, Dong-Liang,Wink, Donald J.,Anderson, Laura L.
supporting information, p. 13217 - 13225 (2016/02/19)
A solvent-controlled cascade process has been identified for the dual purpose of the preparation of either dihydrocarbazoles or dihydropyridoindoles from identical N-aryl-α,β-unsaturated nitrones and electron-deficient allene starting materials. These reactions proceed smoothly under mild metal-free conditions affording a range of two types of skeletally distinct indole-based heterocycles in high yield and diastereoselectivity. These transformations demonstrate the use of a bifurcated cascade process that hinges on the ring-opening event of a benzazepine intermediate for the synthesis of skeletally diverse heterocyclic products and rapid access to biologically-significant, indole-based structures.
