✍ Scribed by Hoai V. Dang; Wolfgang Stadlbauer
No coin nor oath required. For personal study only.
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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.
📜 SIMILAR VOLUMES
4-Hydroxy-5-phenylpyrido[3,2,1-jk]carbazol-6-ones (4, 5), which were obtained from carbazoles 1 and malonates 2 or 3, were converted to reactive intermediates such as 4-chlorides 9 or 4-tosylates 10, which gave in turn 4-azido-5-phenyl derivatives 11. 5-Alkyl-4-azides 11 were not obtained in this ma
## Abstract magnified image Tetrahydrocarbazoles **4** obtained from phenylhydrazines and cyclohexanones gave by cyclocondensation with 2‐substituted malonates **5** in all cases 4‐hydroxy‐8,9,10,11‐tetrahydropyrido[3,2,1‐__jk__]carbazol‐6‐ones **6** by attack at the nitrogen and the aromatic ring
## Abstract Pyrido[3,2,1‐__jk__]carbazoles **1**, synthesized from carbazoles and alkyl‐ or arylmalonates, gave regioselective electrophilic substitution reactions at position 5 such as chlorination to 5‐chloro derivatives **2**, nitration to 5‐nitro compounds **3**, or hydroxylation to 5‐hydroxy d