Synthesis and structure elucidation of 3,4-dihydroxy-2-quinolin-2-ylpyrido[3,2,1-jk]carbazol-6-ones
✍ Scribed by Hoai V. Dang; Nargues S. Habib; Thomas Kappe; Klaus Zangger; Wolfgang Stadlbauer
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2007
- Tongue
- English
- Weight
- 346 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
2,
carbazol-6-ones 6 were obtained by cyclocondensation of carbazole 1 with malonates 2 in the presence of quinoline. The assignment of the structures of 6 was performed by NMR experiments such as 1D 1 H, 13 C and DEPT, as well as 2D COSY, HSQC, HMBC and 1,1-ADEQUATE spectra.
📜 SIMILAR VOLUMES
## Abstract magnified image 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‐
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 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
## 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