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Oxidative transformations of 2,4-dioxo-3-(3-hydroxybutyl)-1,2,3,4,6,7-hexahyidro-11bH-benzo[a]quinolizine

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The oxidation of 2,4-dioxo-3-(3-hydroxybutyl)-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine with either the Sarett complex or Jones reagent gives predominantly 5-oxo-2-methyl-2,3,7,8-tetrahydro-4H,5H-benzo[a]pyrano[2,3-g]quinolizine, while oxidation with CrO3 in AcOH solution gives 8,9,14-trioxo-12-methyl-5,6,8,9,10,11,15,15a-octahydro-13-oxa-12H,14H-azepino[2,1-a]isoquinoline.

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Literature cited

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1611–1614, July, 1973.

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Akhrem, A.A., Moiseenkov, A.M. & Malishevskii, V.S. Oxidative transformations of 2,4-dioxo-3-(3-hydroxybutyl)-1,2,3,4,6,7-hexahyidro-11bH-benzo[a]quinolizine. Russ Chem Bull 22, 1559–1561 (1973). https://doi.org/10.1007/BF00930061

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  • Oxidation
  • AcOH
  • Isoquinoline
  • Oxidative Transformation
  • Jones Reagent