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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Published in | Tetrahedron letters Vol. 54; no. 19; pp. 2386 - 2390 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
08.05.2013
Elsevier |
Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2013.02.092 |