A convenient route to quinolone-fused imides and lactams: Synthesis of pyrrolo[3,4-b]quinoline-3,9-diones and 1,3,9-triones by oxidation of indole derivatives

Pyrrolo[3,4-b]quinoline-3,9-diones have been obtained by Winterfeldt's oxidation (O-2, t-BuOK, DMF) of readily available N(b)substituted tetrahydropyrido[3,4-b]indol-1-ones (tetrahydrocarbazol-1-ones). Surprisingly, the oxidation using N(b)-unsubstituted analogue as starting material afforded u...

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Published inSynlett no. 10; pp. 1071 - 1073
Main Authors Tratrat, C, Giorgi-Renault, S, Husson, HP
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
oxidation
indole
pyrrolo[3,4-b]quinoline-1,9-dione
pyrrolo[3,4-b]quinoline-1,3,9-trione
pyrrolo[3,4-b]quinoline-3,9-dione
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Summary:Pyrrolo[3,4-b]quinoline-3,9-diones have been obtained by Winterfeldt's oxidation (O-2, t-BuOK, DMF) of readily available N(b)substituted tetrahydropyrido[3,4-b]indol-1-ones (tetrahydrocarbazol-1-ones). Surprisingly, the oxidation using N(b)-unsubstituted analogue as starting material afforded under the same conditions pyrrolo[3,4b]quinoline-1,3,9-trione. The difference in reactivity was interpreted. Two unknown pyrrolo[3,4-b]quinoline-1,9-dione derivatives have been synthesized by regioselective reduction of the imide function.
ISSN:0936-5214
DOI:10.1055/s-1998-1856