Synthesis of Chloramphenicol via a new Intermediate 4-para-Nitrophenyl-5-formamido-1,3-dioxane

Synthesis of Chloramphenicol via a new Intermediate 4-para-Nitrophenyl-5-formamido-1,3-dioxane

4-Phenyl-5-amino-1,3-dioxane 4, obtained from β-bromo styrene 2 was protected as formamido derivative 5. Nitration of 5 followed by regioselective acylative cleavage of the nitro product 12 gave N-formyl-N-acetyl hemiacetal diacetate 16, which on sequential base and acid hydrolysis followed by dichl...

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Veröffentlicht in:Synthetic communications 1997-06, Vol.27 (11), p.1857-1864
Hauptverfasser: Hazra, Braja G, Pore, Vandana S., Maybhate, Shailaja P.
Format: Artikel
Sprache:eng
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Zusammenfassung:4-Phenyl-5-amino-1,3-dioxane 4, obtained from β-bromo styrene 2 was protected as formamido derivative 5. Nitration of 5 followed by regioselective acylative cleavage of the nitro product 12 gave N-formyl-N-acetyl hemiacetal diacetate 16, which on sequential base and acid hydrolysis followed by dichloroacetylation gave chloramphenicol 1.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397919708006786