Meisenheimer Rearrangement of Azetopyridoindoles. III. Synthesis of 3,6-Epoxyhexahydroazocino(5,4-b) indoles.

摘要: Oxidation of 2-ethylhexahydroazeto[1', 2' : 1, 2]pyrido[3, 4-b]indole-1-carboxylate 9 with m-chloroperbenzoic acid in methylene dichloride at -5°C gava the corresponding cis-N-oxide 10, which was spontaneously transformed tetrahydrofuran to 3, 6-epoxy-1, 2, 4, 5, 6-hexahydroazocino[5, 4-b]indole 11 (75%) via [1, 2]-Meisenheimer rearrangement, along a formation isoxazolidinone 12 (6.4%) through Cope elimination. The structural assignment azocinoindole accomplished, mainly based on 1H-NMR spectrum and also by chemical transformation 14.