No abstract

We have demonstrated a scalable chemoselective reduction of a nitro functional group in the presence of an aryl imine using (NH 4 ) 2 S/EtOH or hydrogenation (Sponge Nickel) to afford the corresponding amino-imines in moderate to excellent yields. Other reducible groups such as aryl halides, styryl olefins, and ether linkages survived as well.

No abstract

Short, efficient pathways are described for the synthesis of racemic 2-nitroimidazole radiation sensitizer RB-6145 (2a) and each of its corresponding (R)-and (S)-enantiomers (2b and 2c, respectively). The synthesis of each enantiomer commences with the appropriate chiral epichlorohydrin and utilizes a novel application of 3-trimethylsilyl-2-oxazolidinone (3b) as a mild, safe surrogate for highly toxic aziridine. The synthesis of the (R)-enantiomer (2b) has been successfully scaled up to provide multi-kilo quantities of material for early stage preclinical evaluation.

Short, efficient pathways are described for the synthesis of racemic 2‐nitroimidazole radiation sensitizer RB‐6145 (2a) and each of its corresponding (R)‐ and (S)‐enantiomers (2b and 2c, respectively). The synthesis of each enantiomer commences with the appropriate chiral epichlorohydrin and utilizes a novel application of 3‐trimethylsilyl‐2‐oxazolidinone (3b) as a mild, safe surrogate for highly toxic aziridine. The synthesis of the (R)‐enantiomer (2b) has been successfully scaled up to provide multi‐kilo quantities of material for early stage preclinical evaluation.