A copper-catalyzed annulation of oxime acetates and α-amino acid ester derivatives for the easy preparation of 4-pyrrolin-2-ones bearing a 3amino group has been developed. This process features the oxidation of amines with oxime esters as the internal oxidant to produce the active 1,3dinucleophilic and 1,2-dielectrophilic species concurrently. The subsequent nucleophilic cyclization realizes the efficient construction of 4-pyrrolin-2-one derivatives.
A copper-catalyzed bisannulation reaction of malonate-tethered O-acyl oximes with pyridine, pyrazine, pyridazine, and quinoline derivatives has been developed for the concise synthesis of structurally novel dihydroindolizine-fused pyrrolidinones and their analogues. The present reaction shows excellent regioselectivity and stereoselectivity. Theoretical calculations reveal that the coordination effect of the carbonyl group in the nucleophilic substrate determines the excellent regioselectivity. Further functionalization of the generated dihydroindolizine-fused pyrrolidinone could be easily realized through substitution, Michael addition, selective aminolysis, and hydrolysis reactions.
In this work, a novel energy-efficient distillation technology combining reactive dividing-wall column (RDWC) with vapor recompression heat pump (VRHP) is proposed. The integrated RDWC with VRHP models with intermediate reboiler or bottom reboiler are designed for reaching better energy-savings and economic performance. The results showed that the reactive dividing-wall column with vapor recompression heat pump and intermediate reboiler is more attractive than the reactive dividing-wall column with vapor recompression heat pump and bottom reboiler in this study. Adding a preheater to the reactive dividing-wall column with vapor recompression heat pump and intermediate reboiler (RDWC-VRHP-IR2) can further reduce the compression ratio and reach better performance. The RDWC-VRHP-IR2 saves 57.06% of total utility consumption, 31.31% of total annual cost with the payback period of 5 years, and 61.52% of CO 2 emissions compared with the conventional two-column reactive distillation system.
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