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Amination of pyrido[3,2,1‐ jk ]carbazol‐6‐ones
Author(s) -
Dang Hoai V.,
Stadlbauer Wolfgang
Publication year - 2006
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.5570430110
Subject(s) - chemistry , amination , benzylamine , piperidine , aniline , reductive amination , catalysis , medicinal chemistry , catalytic hydrogenation , ring (chemistry) , organic chemistry
Amination of 4‐hydroxypyridocarbazolones 1 with aniline or benzylamine gave in good yields 4‐amines 3 . With piperidine in a sealed tube from 4‐hydroxy‐ or 4‐chloro‐5‐alkylpyridocarbazolones 1 or 4 ring opened 1‐acylcarbazoles 5 were obtained. Only 4‐hydroxy‐5‐phenyl‐pyridocarbazolone 1d gave 4‐amines 6 . Reduction of 4‐azidopyridocarbazolones 7 either by catalytic hydrogenation or in a 2‐step synthesis via phosphazenes 8 gave 4‐aminopyridocarbazolones 9 . Amines 9 were also obtained from benzylamines 3 by catalytic debenzylation. A one step amination of 4‐hydroxy‐5‐phenylpyridocarbazolone 1d via debenzylation to 9d was observed by reaction with benzylammonium chloride. At elevated temperatures the highly fused 6,13b‐diazaindeno[1,2,3‐ hi ]chrysenone 10 was formed from 1d .