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Synthesis and reactions of 10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones
Author(s) -
Kappe Thomas,
Frühwirth Franz,
Roschger Peter,
Jocham Brigitte,
Kremsner Jenny,
Stadlbauer Wolfgang
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390224
Subject(s) - chemistry , nitration , sulfuryl chloride , amination , bromine , nitro , medicinal chemistry , organic chemistry , catalysis , alkyl
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.