29342-32-3Relevant academic research and scientific papers
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.
Synthesis of 5-alkyl-5-aryl-1-pyrroline N-oxides from 1-aryl-substituted nitroalkanes and acrolein via Michael addition and nitro reductive cyclization
Xu, Jingjing,Li, Xingyao,Wu, Jinlong,Dai, Wei-Min
, p. 6384 - 6391 (2015/03/30)
A general method for accessing 5-alkyl-5-aryl-1-pyrroline N-oxides (AAPOs) has been established using readily available aryl bromides, nitroalkanes, and acrolein as the starting materials. The palladium-catalyzed arylation of nitroalkanes gave the 1-aryl-substituted nitroalkanes, which underwent the Et3N-catalyzed Michael addition with acrolein at room temperature to afford the 4-aryl-4-nitroaldehydes. The latter were then subjected to the nitro reductive cyclization using Zn-HOAc in EtOH at 0 °C followed by warming the reaction mixture to room temperature for 24 h, furnishing the 5-alkyl-5-aryl-1-pyrroline N-oxides in good overall yields. Selected examples of 1,3-dipolar cycloaddition of the cyclic nitrones with methyl methacrylate were also described.
