One Pot Synthesis of Substituted Dihydroindeno[1,2-b]indoles and Dihydrobenzo[a]carbazoles by Photostimulated Reactions of o-Iodoaniline with Carbanions by the SRN1 Mechanism

SILVIA M. BAROLO; CECIRÉ ROSALES; JORGE E. ANGEL GUÍO; ROBERTO A. ROSSI*

JOURNAL OF 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 SRN1 mechanism in one pot reactions.