Reactivite photochimique des α-aminoenones: reactions de cyclisation et nouveau type de reaction dans les α-sulfonamido-cyclohexenones

Arnould, J.C.; Cossy, Janine; Pete, Jean‐Pierre

doi:10.1016/s0040-4020(01)83126-4

Cited by 19 publications

(7 citation statements)

References 27 publications

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“…31 Finally, the method has been extended to N-arylenaminones where the amine is bound to the a-carbon of the enone, and bond formation occurs to its b-carbon (Table 5). 32 As with the aforementioned examples, the cyclohexanone derivatives 27a-c each gave the corresponding indoles 28a-c in good yield after a residence time of 1 h, while the yield for cyclisation of the acyclic enone 27d to indole 28d was modest. In conclusion, we have developed a cheap, efficient and atom economic route to indoles that has wide applicability.…”

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confidence: 59%

New approaches to ondansetron and alosetron inspire a versatile, flow photochemical method for indole synthesis

et al. 2022

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mentioning

confidence: 59%

New approaches to ondansetron and alosetron inspire a versatile, flow photochemical method for indole synthesis

et al. 2022

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“…Yellow solid (93%), m.p. : 46 -488C (lit [35], 49 -508C). 9-Butyl-1,2,3,4-tetrahydrocarbazole-1-one 4c…”

Section: -Ethyl-1234-tetrahydrocarbazole-1-one 4bmentioning

confidence: 99%

Synthesis and In‐Vitro Antitumor Activities of Some Mannich Bases of 9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones

Chen

Lou

Liu

et al. 2009

Archiv der Pharmazie

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A novel series of 2-substituted aminomethyl-9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones 5a-q was synthesized via aminomethylation of 9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones 4a-e with hydrochlorides of the respective amines 6a-m. The structures of these newly synthesized compounds were characterized by (1)H-NMR, MS, and elemental analysis. All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines including human non-small lung cancer cells (A549), human gastric adenocarcinoma (SGC), human colon cancer cell (HCT116), human myeoloid leukemia cells (K562), and one multi-drug resistant subline (KB-VCR). Most compounds showed moderate to potent cytotoxic activity against the tested cell lines. Preliminary mechanism research indicated that the most promising compound, 2-diethylaminomethyl-9-methyl-1,2,3,4-tetrahydrocarbazole-1-one 5c, exhibited a potential inhibitory effect against microtubule.

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“…Enaminones of type 148, on irradiation in a mixture of benzene/methanol solvent, undergo a smooth cyclization (Scheme 8.43) to produce the corresponding indolones 150 in high yield [73][74][75].…”

Section: Photochemical Electrocyclization Reactions: Synthesis Of Fusmentioning

confidence: 99%

Formation of a Five‐Membered Ring

Pandey

Gadre

2009

Handbook of Synthetic Photochemistry

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Reactivite photochimique des α-aminoenones: reactions de cyclisation et nouveau type de reaction dans les α-sulfonamido-cyclohexenones

Cited by 19 publications

References 27 publications

New approaches to ondansetron and alosetron inspire a versatile, flow photochemical method for indole synthesis

New approaches to ondansetron and alosetron inspire a versatile, flow photochemical method for indole synthesis

Synthesis and In‐Vitro Antitumor Activities of Some Mannich Bases of 9‐Alkyl‐1,2,3,4‐tetrahydrocarbazole‐1‐ones

Formation of a Five‐Membered Ring

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