Abstract
A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from easily accessible 2H-azirines and aldehydes under mild reaction conditions. The potential of this strategy was further demonstrated by the rapid synthesis of a cyclooxygenase-2 inhibitor as well as the success of employing electron-deficient alkenes and imines as the reaction partners.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry*
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Alkenes / chemistry
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Azirines / chemistry*
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Catalysis
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Cycloaddition Reaction
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Cyclooxygenase 2 Inhibitors / chemical synthesis*
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Cyclooxygenase 2 Inhibitors / chemistry
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Cyclooxygenase 2 Inhibitors / pharmacology
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Imines / chemistry
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Light
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Molecular Structure
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Oxazoles / chemical synthesis*
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Oxazoles / chemistry
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Oxazoles / pharmacology
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Oxidation-Reduction
Substances
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Aldehydes
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Alkenes
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Azirines
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Cyclooxygenase 2 Inhibitors
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Imines
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Oxazoles