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Paper | Regular issue | Vol 48, No. 10, 1998, pp.2061-2070
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8250
Unprecedented Base-promoted Oxidation of Imidazo[1',5':1,2]pyrido[3,4-b]indoles

Natalia De la Figuera, Ma Teresa García-López, Rosario Herranz, and Rosario González-Muñiz*

*Instituto de Química Médica, C. S. I. C., Calle Juan de Cierva, 3, E-28006 Madrid, Spain


1,3-Dioxotetrahydro-1H-imidazo[1’,5’:1,2]pyrido[3,4-b]indole derivatives show a high tendency towards the oxidation at the 11b-bridgehead position in basic media. This oxidation, affording the corresponding 11b-hydroxy derivatives, is produced by reaction between atmospheric oxygen and the imidazopyrido derivative under the enol form and can be suppressed by working in inert atmosphere. In marked contrast, these imidazo[1’,5’:1,2]pyrido derivatives are completely stable in acidic conditions.