Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 14, Pages 3420-3429Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900323
Keywords
nitromethane; aldehydes; isoxazoles; copper acetate; nitrogen heterocycles
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Funding
- National Natural Science Foundations of China [21572049]
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A copper acetate-mediated reaction of benzaldehydes with nitromethane to synthesis of 3-nitroisoxazoles is reported. A variety of nitro-aryl-disubstituted isoxazole derivatives can be prepared in moderate to good yields with benign functional group tolerance. This protocol is successfully applied in gram-scale reaction. Preliminary mechanistic studies reveal that the aldehyde provided one carbon atom for the isoxazole ring, and nitromethane provided two carbon atoms and one nitrogen atom for the isoxazole ring. In this protocol, the C-O-N unit in the final isoxazole ring is formed from the rearrangement of nitromethane.
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