通过顺序[3 + 2]环加成/硅基交叉偶联反应合成3,4,5-三取代异恶唑。
Synthesis of 3,4,5-trisubstituted isoxazoles via sequential [3 + 2] cycloaddition/silicon-based cross-coupling reactions.
作者信息
Denmark Scott E, Kallemeyn Jeffrey M
机构信息
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
出版信息
J Org Chem. 2005 Apr 1;70(7):2839-42. doi: 10.1021/jo047755z.
PMID:15787583
Abstract
[reaction: see text] A [3 + 2] cycloaddition reaction between alkynyldimethylsilyl ethers and aryl and alkyl nitrile oxides to produce isoxazolylsilanols has been developed. The cross-coupling reactions of these heterocyclic silanols with a variety of aryl iodides affords 3,4,5-trisubstituted isoxazoles. This sequential process allows for rapid variation of substituents at the 3, 4, and 5 positions of the isoxazole.
摘要
[反应：见正文] 已开发出炔基二甲基甲硅烷基醚与芳基和烷基腈氧化物之间的[3 + 2]环加成反应，以生成异恶唑基硅醇。这些杂环硅醇与各种芳基碘的交叉偶联反应可得到3,4,5-三取代异恶唑。这个连续过程允许在异恶唑的3、4和5位快速改变取代基。
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