Ethyl α-nitrocinnamates in the synthesis of highly functionalized isoxazoles

Kuang Po Chen; Yu Jyun Chen; Che Ping Chuang

doi:10.1002/ejoc.201000401

Ethyl α-nitrocinnamates in the synthesis of highly functionalized isoxazoles

Kuang Po Chen, Yu Jyun Chen, Che Ping Chuang

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

An effective method for the synthesis of highly functionalized isoxazoles from readily available starting ethyl α-nitrocinnamates has been developed. Ethyl α-nitrocinnamates react smoothly with α-nitro carbonyl compounds to produce isoxazoles in good yields. Michael addition of pyridinium ylides to ethyl α-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.

Original language	English
Pages (from-to)	5292-5300
Number of pages	9
Journal	European Journal of Organic Chemistry
Issue number	27
DOIs	https://doi.org/10.1002/ejoc.201000401
Publication status	Published - 2010 Sep 1

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "An effective method for the synthesis of highly functionalized isoxazoles from readily available starting ethyl α-nitrocinnamates has been developed. Ethyl α-nitrocinnamates react smoothly with α-nitro carbonyl compounds to produce isoxazoles in good yields. Michael addition of pyridinium ylides to ethyl α-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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Ethyl α-nitrocinnamates in the synthesis of highly functionalized isoxazoles

Abstract

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