Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 27, Pages 5292-5300Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000401
Keywords
Nitrogen heterocycles; Michael addition; Alkylation; Multicomponent reactions
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Funding
- National Science Council of ROC [NSC-98 2113-M-006-003-MY2]
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An effective method for the synthesis of highly functionalized isoxazoles from readily available starting ethyl u-nitrocinnamates has been developed. Ethyl u-nitrocinnamates react smoothly with alpha-nitro carbonyl compounds to produce isoxazoles in good yields. Michael addition of pyridinium ylides to ethyl alpha-nitrocinnamates can also produce these isoxazoles effectively. These pyridinium salts can be generated in situ from the corresponding alkyl bromides. The one-pot multicomponent process was also developed. Isoxazoles can be produced directly from readily available aromatic aldehydes, ethyl nitroacetate, and pyridinium salts.
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