Kumar Das Deb, Kannaujiya Vinod Kumar, Sadhu Milon M, Ray Sumit Kumar, Singh Vinod K
Department of Chemistry , Indian Institute of Science Education and Research Bhopal , Bhopal , MP 462066 , India.
Department of Chemistry , Indian Institute of Technology Kanpur , Kanpur , UP 208016 , India.
J Org Chem. 2019 Dec 20;84(24):15865-15876. doi: 10.1021/acs.joc.9b02127. Epub 2019 Nov 27.
BF·OEt-catalyzed nucleophilic addition of vinyl azides to in situ generated -acyl iminium salts obtained from 3-hydroxyisoindolinones is described in this article. The procedure is operationally simple, mild, additive, and metal-free. The reaction proceeds smoothly at ambient temperature with a wide range of 3-hydroxyisoindol-1-ones and vinyl azides to afford 3-oxoisoindoline-1-acetamides (32 examples) in high yields (up to 97%). Furthermore, the synthetic utility of this methodology is depicted by exploiting the reactivity of an amide functionality in the products.
本文描述了BF·OEt催化的叠氮乙烯对由3-羟基异吲哚啉酮原位生成的α-酰基亚胺盐的亲核加成反应。该方法操作简单、温和、无需添加剂且无金属。反应在室温下顺利进行，适用于多种3-羟基异吲哚-1-酮和叠氮乙烯，能以高产率（高达97%）得到3-氧代异吲哚啉-1-乙酰胺（32个实例）。此外，通过利用产物中酰胺官能团的反应活性，展示了该方法的合成实用性。
