6533b854fe1ef96bd12ade64

RESEARCH PRODUCT

Polycondensed nitrogen heterocycles. Part25. Aminopyrrolo[1,2-f]-phenanthridines by decomposition of 2-(3-azidophenyl)-1-arylpyrroles

Anna Maria AlmericoGirolamo CirrincioneFrancesco MingoiaEnrico AielloGaetano Dattolo

subject

chemistry.chemical_compoundHydrolysisAcid catalysischemistryNucleophileArylOrganic ChemistryOrganic chemistryAzideHydrogen atom abstractionRing (chemistry)DecompositionMedicinal chemistry

description

Acid catalyzed decomposition of the azido derivatives 4a-c gave rise to amino-hydroxy-phenylpyrroles of type 7 and 8 upon hydrolysis of the intermediate aryl nitrenium ions, together with the hydrogen abstraction compounds of type 3. The aminopyrrolo[1,2-f]phenanthridines 10, 11, and 12 were obtained by treatment with TFMSA of the azide 4d in which the ring being attacked was made more nucleophilic by the introduction of the methoxy group.

yearjournalcountryeditionlanguage
1994-01-01Journal of Heterocyclic Chemistry
https://doi.org/10.1002/jhet.5570310132