29342-33-4Relevant academic research and scientific papers
Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy
Ushakov, Pavel Yu.,Khatuntseva, Elizaveta A.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.,Sukhorukov, Alexey Yu.
, p. 5322 - 5327 (2019/11/13)
A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N?O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated. (Figure presented.).
Synthesis of 5-alkyl-5-aryl-γ-lactams from 1-aryl-substituted nitroalkanes and methyl acrylate via Michael addition and reductive lactamization
Xu, Jingjing,Li, Xingyao,Wu, Jinlong,Dai, Wei-Min
, p. 3839 - 3846 (2014/06/09)
A general method for accessing 5-alkyl-5-aryl-γ-lactams has been developed using readily available aryl bromides, nitroalkanes, and methyl acrylate as the starting materials. The palladium-catalyzed arylation of nitroalkanes gave the 1-aryl-substituted nitroalkanes, which underwent the DBU-mediated Michael addition with methyl acrylate at room temperature to afford the methyl 4-aryl-4-nitroalkanoates. The latter were then subjected to the nitro reduction using NaBH4-NiCl2·6H2O in MeOH at 0 °C to furnish, after treatment with aqueous K 2CO3 at room temperature, the 5-alkyl-5-aryl-γ- lactams in good to excellent overall yields. Selected examples of N-alkylation of the γ-lactams were also illustrated.
