One pot synthesis of substituted dihydroindeno[1,2-b]indoles and dihydrobenzo[a]carbazoles by photostimulated reactions of o- iodoaniline with carbanions by the S(RN)1 mechanism

BAROLO,S.M.; ROSALES,C.; GUIO,J.E.A.; ROSSI,R.A.

Journal Heterocyclic Chemistry

Año: 2006 vol. 43 p. 695 - 699

0022-152X

The photostimulated reaction of enolate anions of cyclic aromatic ketones such as substituted indan-1-ones and 3,4-dihydro-2H- naphthalen-1-one with o-iodoaniline in DMSO affords 1-, 2-, 3-, and 4- methoxy-5,10-dihydroindeno[1,2-b]indoles (34-40%), 1,2-, 1,4-, and 2,3-dimethoxy-5,10-dihydroindeno[1,2-b]indoles (31-43%), and 1-, 2-, and 3-methoxy-5,11-dihydro-6H-benzo[a]carbazoles (42-61%) by the S(RN)1 mechanism in one pot reactions