e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthese de dihydro-6, 7 5H-pyrimidino (5, 4-c) carbazoles et de 7H-pyrimidino (5, 4-c) carbazoles.

JC LANcELoT, JM GAzENGEL…

Index: Lancelot, Jean-Charles; Gazengel, Jean-Marie; Robba, Max Chemical & Pharmaceutical Bulletin, 1983 , vol. 31, # 8 p. 2652 - 2661

Full Text: HTML

Citation Number: 11

Abstract

The synthesis of 6, 7-dihydro-5H-pyrimidino [5, 4-c] carbazoles (3) was achieved by cyclisation of 1, 2, 3, 4-tetrahydrocarbazol-4-ones with triformamidomethane. The oxydation with potassium permanganate of 6, 7-dihydro-5H-pyrimidino [5, 4-c] carbazoles gave the 7H- pyrimidino [5, 4-c] carbazoles (4). The reactions of the pyrimidinocarbazoles (4a) and (4e) with lithium organic compounds afforded 4-substituted derivatives (6). The structure of the ...

4-Chlorophenylhydrazine hydrochloride Structure

4-Chlorophenylh...

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

~63%

6-chloro-1,2,3,9-tetrahydrocarbazol-4-one Structure

6-chloro-1,2,3,...

Diethyl sulfate Structure

Diethyl sulfate

2,3-Dihydro-1H-carbazol-4(9H)-one Structure

2,3-Dihydro-1H-...

~89%

9-ethyl-2,3-dihydro-1H-carbazol-4-one Structure

9-ethyl-2,3-dih...

4-Methylphenylhydrazine hydrochloride Structure

4-Methylphenylh...

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

~67%

4H-Carbazol-4-one,1,2,3,9-tetrahydro-6-methyl- Structure

4H-Carbazol-4-o...

dihydro-6,7 chloro-10 5H-pyrimidino<5,4-c>carbazole Structure

dihydro-6,7 chl...

~53%

10-chloro-7H-pyrimido[5,4-c]carbazole Structure

10-chloro-7H-py...

5H-Pyrimido[5,4-c]carbazole, 10-fluoro-6,7-dihydro- Structure

5H-Pyrimido[5,4...

~68%

10-fluoro-7H-pyrimido[5,4-c]carbazole Structure

10-fluoro-7H-py...

5H-Pyrimido[5,4-c]carbazole, 9-chloro-6,7-dihydro- Structure

5H-Pyrimido[5,4...

~34%

9-chloro-7H-pyrimido[5,4-c]carbazole Structure

9-chloro-7H-pyr...

5H-Pyrimido[5,4-c]carbazole, 6,7-dihydro- Structure

5H-Pyrimido[5,4...

~29%

7H-pyrimido[5,4-c]carbazole Structure

7H-pyrimido[5,4...

5H-Pyrimido[5,4-c]carbazole, 6,7-dihydro-7-methyl- Structure

5H-Pyrimido[5,4...

~19%

7-methylpyrimido[5,4-c]carbazole Structure

7-methylpyrimid...

Formamide, N,N,N-methylidynetris- Structure

Formamide, N,N,...

6-chloro-9-methyl-2,3-dihydro-1H-carbazol-4-one Structure

6-chloro-9-meth...

~48%

5H-Pyrimido[5,4-c]carbazole, 10-chloro-6,7-dihydro-7-methyl- Structure

5H-Pyrimido[5,4...

1,2,3,4-Tetrahydro-9-methylcarbazol-4-one Structure

1,2,3,4-Tetrahy...

Formamide, N,N,N-methylidynetris- Structure

Formamide, N,N,...

~29%

5H-Pyrimido[5,4-c]carbazole, 6,7-dihydro-7-methyl- Structure

5H-Pyrimido[5,4...

Formamide, N,N,N-methylidynetris- Structure

Formamide, N,N,...

7-chloro-1,2,3,9-tetrahydrocarbazol-4-one Structure

7-chloro-1,2,3,...

~34%

5H-Pyrimido[5,4-c]carbazole, 9-chloro-6,7-dihydro- Structure

5H-Pyrimido[5,4...

3-Chloro Phenyl Hydrazine Hydrochloride Structure

3-Chloro Phenyl...

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

~51%

7-chloro-1,2,3,9-tetrahydrocarbazol-4-one Structure

7-chloro-1,2,3,...

dihydro-6,7 dichloro-8,10 5H-pyrimidino<5,4-c>carbazole Structure

dihydro-6,7 dic...

~51%

8,10-dichloro-7H-pyrimido[5,4-c]carbazole Structure

8,10-dichloro-7...

1-Bromobutane Structure

7H-pyrimido[5,4-c]carbazole Structure

7H-pyrimido[5,4...

~55%

4-butyl-4,7-dihydro-1H-pyrimido[5,4-c]carbazole Structure

4-butyl-4,7-dih...

5H-Pyrimido[5,4-c]carbazole, 6,7-dihydro- Structure

5H-Pyrimido[5,4...

~%

4-butyl-4,7-dihydro-1H-pyrimido[5,4-c]carbazole Structure

4-butyl-4,7-dih...

4-butyl-4,7-dihydro-1H-pyrimido[5,4-c]carbazole Structure

4-butyl-4,7-dih...

~59%

4-butyl-7H-pyrimido[5,4-c]carbazole Structure

4-butyl-7H-pyri...

5H-Pyrimido[5,4-c]carbazole, 6,7-dihydro- Structure

5H-Pyrimido[5,4...

~%

4-butyl-7H-pyrimido[5,4-c]carbazole Structure

4-butyl-7H-pyri...

7H-pyrimido[5,4-c]carbazole Structure

7H-pyrimido[5,4...

~%

4-butyl-7H-pyrimido[5,4-c]carbazole Structure

4-butyl-7H-pyri...

1-(2,4-dichlorophenyl)hydrazine hydrochloride Structure

1-(2,4-dichloro...

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

~54%

6,8-dichloro-1,2,3,9-tetrahydrocarbazol-4-one Structure

6,8-dichloro-1,...

4H-Carbazol-4-one,1,2,3,9-tetrahydro-6-methyl- Structure

4H-Carbazol-4-o...

Dimethyl sulfate Structure

Dimethyl sulfate

~82%

6,9-dimethyl-2,3-dihydro-1H-carbazol-4-one Structure

6,9-dimethyl-2,...

4-Methylphenylhydrazine hydrochloride Structure

4-Methylphenylh...

~%

6,9-dimethyl-2,3-dihydro-1H-carbazol-4-one Structure

6,9-dimethyl-2,...

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

~%

6,9-dimethyl-2,3-dihydro-1H-carbazol-4-one Structure

6,9-dimethyl-2,...

1-Bromobutane Structure

7-ethylpyrimido[5,4-c]carbazole Structure

7-ethylpyrimido...

~41%

4-butyl-7-ethyl-1,4-dihydropyrimido[5,4-c]carbazole Structure

4-butyl-7-ethyl...

dihydro-5,6 ethyl-7 pyrimidino<5,4-c>carbazole Structure

dihydro-5,6 eth...

~%

4-butyl-7-ethyl-1,4-dihydropyrimido[5,4-c]carbazole Structure

4-butyl-7-ethyl...

4-butyl-7-ethyl-1,4-dihydropyrimido[5,4-c]carbazole Structure

4-butyl-7-ethyl...

~49%

4-butyl-7-ethylpyrimido[5,4-c]carbazole Structure

4-butyl-7-ethyl...

dihydro-5,6 ethyl-7 pyrimidino<5,4-c>carbazole Structure

dihydro-5,6 eth...

~%

4-butyl-7-ethylpyrimido[5,4-c]carbazole Structure

4-butyl-7-ethyl...

7-ethylpyrimido[5,4-c]carbazole Structure

7-ethylpyrimido...

~%

4-butyl-7-ethylpyrimido[5,4-c]carbazole Structure

4-butyl-7-ethyl...

Formamide, N,N,N-methylidynetris- Structure

Formamide, N,N,...

6-methoxy-1,2,3,9-tetrahydrocarbazol-4-one Structure

6-methoxy-1,2,3...

~6%

10-methoxy-6,7-dihydro-5H-pyrimido[5,4-c]carbazole Structure

10-methoxy-6,7-...

5H-Pyrimido[5,4-c]carbazole, 10-chloro-6,7-dihydro-7-methyl- Structure

5H-Pyrimido[5,4...

~30%

7H-Pyrimido[5,4-c]carbazole, 10-chloro-7-methyl- Structure

7H-Pyrimido[5,4...

6-chloro-1,2,3,9-tetrahydrocarbazol-4-one Structure

6-chloro-1,2,3,...

Dimethyl sulfate Structure

Dimethyl sulfate

~72%

6-chloro-9-methyl-2,3-dihydro-1H-carbazol-4-one Structure

6-chloro-9-meth...

4-Chlorophenylhydrazine hydrochloride Structure

4-Chlorophenylh...

~%

6-chloro-9-methyl-2,3-dihydro-1H-carbazol-4-one Structure

6-chloro-9-meth...

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

~%

6-chloro-9-methyl-2,3-dihydro-1H-carbazol-4-one Structure

6-chloro-9-meth...

Cyclopropyl Bromide Structure

Cyclopropyl Bromide

7-ethylpyrimido[5,4-c]carbazole Structure

7-ethylpyrimido...

~59%

4-cyclopropyl-7-ethyl-1,4-dihydropyrimido[5,4-c]carbazole Structure

4-cyclopropyl-7...

dihydro-5,6 ethyl-7 pyrimidino<5,4-c>carbazole Structure

dihydro-5,6 eth...

~%

4-cyclopropyl-7-ethyl-1,4-dihydropyrimido[5,4-c]carbazole Structure

4-cyclopropyl-7...

4-cyclopropyl-7-ethyl-1,4-dihydropyrimido[5,4-c]carbazole Structure

4-cyclopropyl-7...

~60%

4-cyclopropyl-7-ethylpyrimido[5,4-c]carbazole Structure

4-cyclopropyl-7...

dihydro-5,6 ethyl-7 pyrimidino<5,4-c>carbazole Structure

dihydro-5,6 eth...

~%

4-cyclopropyl-7-ethylpyrimido[5,4-c]carbazole Structure

4-cyclopropyl-7...

7-ethylpyrimido[5,4-c]carbazole Structure

7-ethylpyrimido...

~%

4-cyclopropyl-7-ethylpyrimido[5,4-c]carbazole Structure

4-cyclopropyl-7...

4-Anisylhydrazine hydrochloride Structure

4-Anisylhydrazi...

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

~33%

6-methoxy-1,2,3,9-tetrahydrocarbazol-4-one Structure

6-methoxy-1,2,3...

dihydro-5,6 ethyl-7 pyrimidino<5,4-c>carbazole Structure

dihydro-5,6 eth...

~57%

7-ethylpyrimido[5,4-c]carbazole Structure

7-ethylpyrimido...

2,3-Dihydro-1H-carbazol-4(9H)-one Structure

2,3-Dihydro-1H-...

Formamide, N,N,N-methylidynetris- Structure

Formamide, N,N,...

~54%

5H-Pyrimido[5,4-c]carbazole, 6,7-dihydro- Structure

5H-Pyrimido[5,4...

10-methoxy-6,7-dihydro-5H-pyrimido[5,4-c]carbazole Structure

10-methoxy-6,7-...

~31%

10-methoxy-7H-pyrimido[5,4-c]carbazole Structure

10-methoxy-7H-p...

dihydro-5,6 dimethyl-7,10 pyrimidino<5,4-c>carbazole Structure

dihydro-5,6 dim...

~31%

7,10-dimethylpyrimido[5,4-c]carbazole Structure

7,10-dimethylpy...

A mild and effective method to synthesize carbazolones by Cu...

[Yan, Shaoyu; Wu, Haihong; Wu, Nan; Jiang, Yongwen Synlett, 2007 , # 17 p. 2699 - 2702]

A mild and effective method to synthesize carbazolones by Cu...

[Yan, Shaoyu; Wu, Haihong; Wu, Nan; Jiang, Yongwen Synlett, 2007 , # 17 p. 2699 - 2702]

Inhibiting NF-κB-inducing kinase (NIK): Discovery, structure...

[Li, Kexue; McGee, Lawrence R.; Fisher, Ben; Sudom, Athena; Liu, Jinsong; Rubenstein, Steven M.; Anwer, Mohmed K.; Cushing, Timothy D.; Shin, Youngsook; Ayres, Merrill; Lee, Fei; Eksterowicz, John; Faulder, Paul; Waszkowycz, Bohdan; Plotnikova, Olga; Farrelly, Ellyn; Xiao, Shou-Hua; Chen, Guoqing; Wang, Zhulun Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 5 p. 1238 - 1244]

Inhibiting NF-κB-inducing kinase (NIK): Discovery, structure...

[Li, Kexue; McGee, Lawrence R.; Fisher, Ben; Sudom, Athena; Liu, Jinsong; Rubenstein, Steven M.; Anwer, Mohmed K.; Cushing, Timothy D.; Shin, Youngsook; Ayres, Merrill; Lee, Fei; Eksterowicz, John; Faulder, Paul; Waszkowycz, Bohdan; Plotnikova, Olga; Farrelly, Ellyn; Xiao, Shou-Hua; Chen, Guoqing; Wang, Zhulun Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 5 p. 1238 - 1244]