G. Bobowski
Mar 1, 1983
Citations
0
Influential Citations
4
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The condensation of 1H-indole-3-ethanamides, 1, with 2,4-pentanediones, 2, gave enamines 3. Acid catalyzed ring closure of 3 gave 1-(1-substituted-2,3,4,9-tetrahydro- (2-oxopropyl) -1H-pyrido [3,4-b] indoles 4. Subsequent N-acetylation yielded 5 which sequentially produced 2,3-disubstituted indoles 6 and 7 resulting from CN bond cleavage after treatment with sodium alkoxide in ethanol. Controlled catalytic hydrogenation of the latter gave saturated derivatives 8 and 9.