Proceedings of The 10th International Electronic Conference on Synthetic Organic Chemistry, 2006
Oxidative hydroxylation of pyrido[3,2,1-jk]carbazol-6-ones by hydrogen peroxide, peroxy carboxyli... more Oxidative hydroxylation of pyrido[3,2,1-jk]carbazol-6-ones by hydrogen peroxide, peroxy carboxylic acids or nitric acid leads to 5-hydroxypyrido[3,2,1-jk]carbazole-4,6-diones, which give in alkaline solution ring contraction to oxindoles, dioxindoles and ring opening reactions to carbazolyl-hydroxyphenylpropanones depending on the reaction conditions and substituents at position 5. Wittig olefination of 5-hydroxypyrido[3,2,1-jk]carbazole-4,6-diones gives [2-(3-alkyl-3-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolinylidene)]-acetates.
Proceedings of The 8th International Electronic Conference on Synthetic Organic Chemistry, 2004
Reaction of 5-alkyl substituted hydroxy-pyridocarbazoles 3a or chloro-pyridocarbazoles 5 with sec... more Reaction of 5-alkyl substituted hydroxy-pyridocarbazoles 3a or chloro-pyridocarbazoles 5 with secondary amines such as piperidine or morpholine did not lead to the expected amination products such as 10 but gave ring opened products 9. 5-Phenyl substituted pyridocarbazoles 3a, however, reacted in the desired manner to 10. With aniline or benzylamine, in all cases the amino products 11 were obtained. N
Amination of 4-hydroxypyridocarbazolones 1 with aniline or benzylamine gave in good yields 4-amin... more 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.
Proceedings of The 10th International Electronic Conference on Synthetic Organic Chemistry, 2006
Oxidative hydroxylation of pyrido[3,2,1-jk]carbazol-6-ones by hydrogen peroxide, peroxy carboxyli... more Oxidative hydroxylation of pyrido[3,2,1-jk]carbazol-6-ones by hydrogen peroxide, peroxy carboxylic acids or nitric acid leads to 5-hydroxypyrido[3,2,1-jk]carbazole-4,6-diones, which give in alkaline solution ring contraction to oxindoles, dioxindoles and ring opening reactions to carbazolyl-hydroxyphenylpropanones depending on the reaction conditions and substituents at position 5. Wittig olefination of 5-hydroxypyrido[3,2,1-jk]carbazole-4,6-diones gives [2-(3-alkyl-3-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolinylidene)]-acetates.
Proceedings of The 8th International Electronic Conference on Synthetic Organic Chemistry, 2004
Reaction of 5-alkyl substituted hydroxy-pyridocarbazoles 3a or chloro-pyridocarbazoles 5 with sec... more Reaction of 5-alkyl substituted hydroxy-pyridocarbazoles 3a or chloro-pyridocarbazoles 5 with secondary amines such as piperidine or morpholine did not lead to the expected amination products such as 10 but gave ring opened products 9. 5-Phenyl substituted pyridocarbazoles 3a, however, reacted in the desired manner to 10. With aniline or benzylamine, in all cases the amino products 11 were obtained. N
Amination of 4-hydroxypyridocarbazolones 1 with aniline or benzylamine gave in good yields 4-amin... more 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.
Uploads
Papers by Hoai DANG VAN