2,5-二取代-1,3-恶唑的一般制备方法。
General methodology for the preparation of 2,5-disubstituted-1,3-oxazoles.
机构信息
Department of Chemistry, Indiana University, Bloomington, Indiana 47405-7102, USA.
出版信息
Org Lett. 2010 Feb 19;12(4):808-11. doi: 10.1021/ol902833p.
Abstract
Deprotonation of 2-(phenylsulfonyl)-1,3-oxazole (1) readily provides a useful C-5 carbanion that is reactive with a variety of electrophiles. Aldehydes and ketones are useful substrates, and the formation of 5-iodo- and 5-tri-n-butylstannyl oxazoles affords access to cross-coupling reactions. Subsequent nucleophilic displacement of the 2-phenylsulfonyl group provides a general route for the synthesis of 2,5-disubstituted-1,3-oxazoles.
摘要
2-(苯磺酰基)-1,3-噁唑（1）容易脱质子，生成一种有用的 C-5 碳负离子，它可与各种亲电试剂反应。醛和酮是有用的底物，而 5-碘代和 5-三丁基锡基噁唑的形成则可用于交叉偶联反应。随后，2-苯磺酰基的亲核取代为合成 2,5-二取代-1,3-噁唑提供了一种通用途径。
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Total Synthesis of Nominal Diazonamides-Part 2: On the True Structure and Origin of Natural Isolates Funding provided by the NIH (RO1-GM60591), the NSF (CAREER 9984282), the Howard Hughes Medical Institute (junior faculty support), the Robert A. Welch Foundation, and the Advanced Research Program of the Texas Higher Education Coordinating Board. We are grateful to Professor Michael Roth for his time, insight, and advice.名义重氮酰胺的全合成 - 第2部分：天然分离物的真实结构与来源 由美国国立卫生研究院（RO1 - GM60591）、美国国家科学基金会（职业发展奖9984282）、霍华德·休斯医学研究所（青年教师支持）、罗伯特·A·韦尔奇基金会以及德克萨斯高等教育协调委员会高级研究项目提供资金支持。我们感谢迈克尔·罗斯教授抽出时间、提供深刻见解与建议。
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