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[3 + 2] Cycloaddition/Oxidative Aromatization Sequence via Photoredox Catalysis: One-Pot Synthesis of Oxazoles from 2H-Azirines and Aldehydes.
- Source :
-
Organic letters [Org Lett] 2015 Aug 21; Vol. 17 (16), pp. 4070-3. Date of Electronic Publication: 2015 Aug 07. - Publication Year :
- 2015
-
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.
- Subjects :
- Alkenes chemistry
Catalysis
Cycloaddition Reaction
Cyclooxygenase 2 Inhibitors chemistry
Cyclooxygenase 2 Inhibitors pharmacology
Imines chemistry
Light
Molecular Structure
Oxazoles chemistry
Oxazoles pharmacology
Oxidation-Reduction
Aldehydes chemistry
Azirines chemistry
Cyclooxygenase 2 Inhibitors chemical synthesis
Oxazoles chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 17
- Issue :
- 16
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 26250789
- Full Text :
- https://doi.org/10.1021/acs.orglett.5b01994