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Polycondensed nitrogen heterocycles. Part 25 . Aminopyrrolo[1,2‐ f ]‐phenanthridines by decomposition of 2‐(3‐azidophenyl)‐1‐arylpyrroles
Author(s) -
Almerico Anna Maria,
Cirrincione Girolamo,
Dattolo Gaetano,
Aiello Enrico,
Mingoia Francesco
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310132
Subject(s) - chemistry , decomposition , azide , ring (chemistry) , nucleophile , nitrogen , medicinal chemistry , hydrolysis , hydrogen atom abstraction , aryl , ion , hydrogen , organic chemistry , stereochemistry , catalysis , alkyl
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.