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85. Synthesis and Reactions of 10,10-Dimethyl-10H-pyrido[1,2-a]indol-6-ones
Kappe Th., Frühwirth F., Roschger P., Jocham B., Kremsner J., Stadlbauer, J. Heterocyclic Chem. 39, 391-397 (2002).

Abstract: Cyclocondensation of 2,3,3-trimethyl-3H-indoles with malonates gives 8-hydroxy-10,10-dimethyl-10H-pyrido[1,2-a]indol-6-ones, which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo-10,10-dimethyl-10H-pyrido[1,2-a]indoles . Amination affords the 8-amino-10,10-dimethyl-10H-pyrido[1,2-a]indol-6-one. Nitration gives either the 10,10-dimethyl-7-nitro-10H-pyrido[1,2-a]indoles or 10,10-dimethyl-7-hydroxy-10H-pyrido[1,2-a]indoles, depending on the conditions.

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abstract scheme