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

Article abstract of DOI:10.1002/jhet.5570390224

Cyclocondensation of 2,3,3-trimethyl-3H-indoles 2 with malonates 3 gives 8-hydroxy-10,10-dimethyl-10H-pyrido[1,2-alindol-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-10H-pyrido[1,2-a]indoles 5, 6, 7 and 8. Amination affords the 8-amino-10,10-dimethyl-10H-pyrido[1,2-a]indol-6-one 9. Nitration gives either the 10,10-dimethyl-7-nitro-10H-pyrido[1,2-a]indoles 10 or 10,10-dimethyl-7-hydroxy-10H-pyrido[1,2-a]indoles 11, depending on the conditions.