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Synthesis of Secondary and Tertiary Oxime Carbamate Derivatives and their Structure‐Dependent Bioactivity
Author(s) -
Sivakumar Rajamanickam,
Thanikachalam Venugopal,
Kim BongGi,
Kim Sung Dong
Publication year - 2017
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11159
Subject(s) - oxime , chemistry , carbamate , thiazole , triphosgene , phosgene , antimicrobial , organic chemistry , combinatorial chemistry
Biologically active novel piperidin‐4‐one oxime carbamates were synthesized from 3‐ethyl‐1‐methyl‐2,6‐diphenylpiperidin‐4‐one oxime, 1,1′‐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 oxime–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.