J. Svetlik, F. Tureček, V. Hanuš
1988
Citations
0
Influential Citations
23
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
Condensations of 4-(2-hydroxyphenyl)but-3-2-one with methyl acetoacetate, pentane-2,4-dione, dimedone, and methyl cyanoacetate under the conditions of the Hantzsch synthesis lead to 9-methyl-8-oxa-10-azatricyclo[7.3.1.02,7]trideca-2,4,6,11-tetraene derivatives and related heterocycles. An analogous condensation with 2-aminopropene-1,1,3-triscarbonitrile yields stereoselectively 11-dicyanomethylene-9-methyl-8-oxa-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-triene-12α-carbonitrile. Under suitable reaction conditions, the condensation of 4-(2-hydroxyphenyl)but-3-en-2-one with cyanamide affords various products with the 9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6,11-tetraene skeleton. Condensation products of salicylaldehyde with acetone, 2-aminopropene-1,1,3-triscarbonitrile, and 3-aminocrotononitrile have been identified.