Three-component couplings for the synthesis of pyrroloquinoxalinones by azomethine ylide 1,3-dipolar cycloaddition chemistry |
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Authors: | Anthony Choi Iain Coldham |
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Institution: | Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK |
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Abstract: | 1-Methyl-3,4-dihydroquinoxalin-2(1H)-one was heated with a range of aldehydes to generate intermediate azomethine ylides which underwent 3 + 2] cycloaddition reactions with N-methyl or N-phenylmaleimide to give substituted tetrahydropyrroloquinoxalinones. Only one (racemic) stereoisomer was formed in each case and the stereochemical outcome was verified by single crystal X-ray analysis. The products from this multicomponent reaction could be oxidised with DDQ to the pyrroloquinoxalinones. |
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Keywords: | Corresponding author Azomethine ylide 1 3-Dipolar cycloaddition Heterocycle Multicomponent reaction |
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