Synthesis of Secondary and Tertiary Oxime Carbamate Derivatives and their Structure‐Dependent Bioactivity

摘要

Biologically active novel piperidina??4a??one oxime carbamates were synthesized from 3a??ethyla??1a??methyla??2,6a??diphenylpiperidina??4a??one oxime, 1,1a?2a??carbonyldiimidazole (CDI), and primary or secondary amines in the presence of sodium hydride as base. Commercially available, cheaper, and safer CDI was utilized as carbonyl source, instead of toxic phosgene/triphosgene and carbon monoxide. The devised method is feasible for primary and secondary amines to make their corresponding oxime carbamate derivatives, through oximea??imidazolide intermediate, in high yield. When the antimicrobial activity of obtained oxime carbamate derivatives was investigated in comparison with streptomycin and amphotericin B as standards, the oxime carbamate containing heteroaromatic thiazole ring exhibits outstanding antimicrobial effectiveness, regardless of bacterial or fungal types.