Synfacts 2011(3): 0259-0259  
DOI: 10.1055/s-0030-1259567
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

α-Nitrocinnamate Esters for the Synthesis of Highly Functionalized Isoxazoles

Contributor(s): Victor Snieckus, Matthew O. Kitching
K.-P. Chen, Y.-J. Chen, C.-P. Chuang*
National Cheng Kung University, Tainan, Taiwan
Further Information

Publication History

Publication Date:
16 February 2011 (online)

Significance

Reported is the reaction of ethyl α-nitrocinnamates with activated α-heteroatom-substituted esters and ketones derivatives to give substituted isoxazoles. Optimization of the procedure was conducted including solvent and base screens. Nucleophilic bases (e.g. piperidine) gave substantial quantities of the amide rather than ­ester isoxazoles. The use of pyridinium salts, separately and prepared in situ, was briefly investigated. A one-pot variant, in which the nitrocinnamate was formed in situ, was also developed.