A highly efficient, safe, and sustainable procedure was developed for the synthesis of various pharmacology-relevant and/or energy-rich nitroesters. It is based on nitration of corresponding alcohols with dinitrogen pentoxide in the liquid 1,1,1,2-tetrafluoroethane medium. The proposed approach is attractive for commercial applications because it offers significant advantages such as mild and clean reaction conditions, low operation pressure, available equipment, scalability, and facile fluid recycling. Structure−NO donor activity correlations were elucidated by an in vitro Griess assay for synthesized nitroesters and the obtained data may be useful for further in vivo experiments.
A convenient synthesis of chiral N-nitro-oxazolidin-2-ones by nitration of α-amino acid derived 1,3-oxazolidin-2-ones containing one or two stereogenic centers with dinitrogen pentoxide in liquefied 1,1,1,2-tetrafluoroethane medium has been developed. The obtained N-nitroheterocycles were converted into enantiomerically pure O-(β-nitraminoalkyl) carbamates by treatment with ammonia or amines in the same solvent. The synthesized N-nitro compounds are slightly toxic in vitro to Human Embryonic Kidney 293 (HEK293) cells.
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