A. Narender, E. Laxminarayana, S. Shankar
2010
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Journal
Heterocyclic Communications
Abstract
Reaction of 2-aminopyridine-3-carbaldehyde with 5,5'-Dimethyl-CycIohexane-l,3-dione afforded 8,8'-dimethyl8,9-dihydro-7H-benzo[b][l,8]naphthyridin-6-one (1). Friedlander condensation of (1) with 2-aminopyridine-3carbaldehyde yielded 6,6-dimethyl-6,7-dihydro-l,8,9,14-tetraaza-pentaphene (2), in good yield. Bromination of (1) with one equivalent of N-Bromosuccinamide gave 7-bromo-8, 9-dihydro-8,8-dimethyIbenzo[b][l,8]naphthyridin6(7H)-one(3). The compound (3) on reaction with one equivalent of [(ethoxycarbonyl)-methylene] triphenylphosphorane (aza-Wittig reaction) gave ethyl 2-(7-bromo-8,9-dihydro-8,8-dimethylbenzo[b][l,8]naphthyridin6(7H)-ylidene)acetate (4). Further the compound (4) on cyclisation with anilines to provide the cyclised compounds, 3,3a,4,5-tetrahydro-4,4-dimethyl-3-phenylindolo[5,4-b][l,8]naphthyridin-2-one (5a-e).