A mild efficient iodine-catalyzed synthesis of novel anticoagulants with 2,8-dioxabicyclo[3.3.1]nonane core

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...

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Bibliographic Details
Published inTetrahedron letters Vol. 54; no. 19; pp. 2386 - 2390
Main Authors Ganguly, Nemai C., Mondal, Pallab, Roy, Sushmita
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.05.2013
Elsevier
Subjects
2,8-Dioxabicyclo[3.3.1]nonane core
Anticoagulants
Chemistry
Chemistry, Organic
Iodine catalyst
Michael-bicycloketalization
Physical Sciences
Science & Technology
Anticoagulants
Michael-bicycloketalization
2,8-Dioxabicyclo[3.3.1]nonane core
Iodine catalyst
MOLECULAR-IODINE
RAT
WARFARIN
ACETALIZATION
REDUCTASE
CONDENSATION
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Summary: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 (10mol%) 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.02.092