Synthesis and reactions of 10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones

Cyclocondensation of 2,3,3‐trimefhyl‐3 H ‐indoles 2 with malonates 3 gives 8‐hydroxy‐10,10‐dimefhyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones 4 , which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10 H ‐pyrido[1,...

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Veröffentlicht in:Journal of heterocyclic chemistry 2002-03, Vol.39 (2), p.391-397
Hauptverfasser: Kappe, Thomas, Frühwirth, Franz, Roschger, Peter, Jocham, Brigitte, Kremsner, Jenny, Stadlbauer, Wolfgang
Format: Artikel
Sprache:eng
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Zusammenfassung:Cyclocondensation of 2,3,3‐trimefhyl‐3 H ‐indoles 2 with malonates 3 gives 8‐hydroxy‐10,10‐dimefhyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones 4 , which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indoles 5, 6, 7 and 8 . Amination affords the 8‐amino‐10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐one 9 . Nitration gives either the 10,10‐dimethyl‐7‐nitro‐10 H ‐pyrido[1,2‐ a ]indoles 10 or 10,10‐dimethyl‐7‐hydroxy‐10 H ‐pyrido[1,2‐ a ]indoles 11 , depending on the conditions.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570390224