89048-95-3Relevant academic research and scientific papers
Formation of Oxygen-bridged Heterocycles in the Hantzsch Synthesis with 4-(2-Hydroxyphenyl)but-3-en-2-one
Svetlik, Jan,Turecek, Frantisek,Hanus, Vladimir
, p. 2053 - 2058 (2007/10/02)
Condensations of 4-(2-hydroxyphenyl)but-3-en-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-azatricyclo2,7>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-azatricyclo2,7>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-diazatricyclo2,7>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.
