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Synthesis 1994; 1994(4): 387-390
DOI: 10.1055/s-1994-25483
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Oxazolo[3′,2′ :1,2]pyrido[3,4-b]indole und [1,3]-Oxazino [3′,2′ :1,2]pyrido[3,4-b]indole durch eine einfache Kondensationsreaktion von 3,4-Dihydro-β-carbolin mit α- bzw. β-Hydroxycarbonsäuren

Klaus Th. Wanner* , Ulrich Weber
  • *Institut für Pharmazie der Freien Universität Berlin, Königin-Luise- Str. 2 + 4, D-14195 Berlin, Germany
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Publication Date:
17 September 2002 (online)

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Oxazolo[3′,2′:1,2]pyrido[3,4-b]indoles and [1,3]-Oxazino[3′,2′:1,2]-pyrido[3,4-b]indoles by a Simple Condensation Reaction of 3,4-Dihydro-β-carboline with α- and β-Hydroxycarboxylic Acids 3,4-Dihydro-β-carboline (3) is reacted with trimethylsilyloxyacyl chlorides 2a, 2b, 7 and 11 to give the 1,3-oxazolidin-4-ones 4a/5a and 4b/5b and the 1,3-oxazin-4-ones 8/9 and 12, respectively, representing a new condensation reaction. The enantiomeric purity of the compounds 4a and 5a derived from (S)-mandelic acid [(S)-1a] is found to be greater than 99.5 ee thus establishing that the procedure is compatible with chiral compounds.