63326-72-7Relevant academic research and scientific papers
Synthesis and structure of 1-substituted benzopyrano-[4′,3′-c] benzo[3″,4″-f]-2,8-dioxabicyclo[3.3.1]nonane
Manolov, Ilia,Maichle-Moessmer, Caecilia,Niquet, Elke
, p. 207 - 212 (2006)
The base catalyzed condensation reaction between 4-hydroxycoumarin and 3-acetylcoumarin (3-benzoylcoumarin) in water at reflux led to the formation of 1-methyl (1-phenyl)-benzopyrano[4′,3′-c]-benzo[3″,4″-f]- 2,8-dioxabicyclo[3.3.1]nonane (2a, b) as final products. When 4-hydroxycoumarin and 3-acetylcoumarin reacted in a glacial acetic acid in the presence of potassium acetate the final product was 7-[3-acetyl-2-oxo-3,4-dihydro-2H-[1] benzopyran-4-yl]methyl-6H,14H,14bH-bis-([1]benzopyrano)[4,3-b:4′, 3′-d]pyran-6,14-dione (4). 4-Hydroxycoumarin and 4-(5-bromo-2- hydroxyphenyl)-3-buten-2-one were condensed in water at reflux and 1-methylcoumarino-[4′,3′-c]-bromobenzo[3″,4″-f]-2, 8-dioxabicyclo[3.3.1]nonane was a final product (3).
A mild efficient iodine-catalyzed synthesis of novel anticoagulants with 2,8-dioxabicyclo[3.3.1]nonane core
Ganguly, Nemai C.,Mondal, Pallab,Roy, Sushmita
supporting information, p. 2386 - 2390 (2013/06/26)
An efficient coupling of 2-hydroxychalcones/α,β-enones with 4-hydroxycoumarin/5,5-dimethylcyclohexyl-1,3-dione (dimedone) has been accomplished to provide access to a novel class of potential anticoagulants with 2,8-dioxabicyclo[3.3.1]nonane core. The reaction proceeds by Michael-bicycloketalization sequence under iodine catalysis (10 mol %) in aqueous ethanol under reflux. Good to excellent yields, impressive selectivity, absence of byproduct formation, avoidance of toxic organic solvents, and utilization of metal-free water-compatible mild Lewis acid catalyst are the key attractive features of this protocol.
