Efficient Synthesis of 3-Hydroxy-1, 4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1, 4-Benzodiazepine Ring (CROSBI ID 134988)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Cepanec, Ivica ; Litvić, Mladen ; Pogorelić, Ivan
engleski
Efficient Synthesis of 3-Hydroxy-1, 4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1, 4-Benzodiazepine Ring
Simple, efficient, and scalable syntheses of 3-hydroxy-1, 4- benzodiazepines, oxazepam (1), and lorazepam (2) were developed. The syntheses are based on the new acetoxylation reaction of the 3-position of the 1, 4-benzodiazepine ring. The reaction involves iodine (20-50 mol %)-catalyzed acetoxylation in the presence of potassium acetate (2 equiv) and potassium peroxydisulfate (1-2 equiv) as a stoichiometric oxidant affording the corresponding 3-acetoxy-1, 4-benzodiazepines in good-to-high yields. The latter were converted by selective saponification to 3-hydroxy-1, 4-benzodiazepines of very high purity (>99.8%) in an overall yield of 83% (oxazepam) and 64% (lorazepam).
oxazepam; lorazepam; acetoxylation
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Podaci o izdanju
10 (6)
2006.
1192-1198
objavljeno
1083-6160
10.1021/op068009u