Lewis 酸催化的 3-(2-苯磺酰胺)丙炔醇的级联反应生成螺[茚并苯并恶唑]。
Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s.
机构信息
Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
出版信息
Org Lett. 2015 Jan 16;17(2):242-5. doi: 10.1021/ol503316e. Epub 2014 Dec 26.
PMID:25541815
Abstract
A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.
摘要
已经开发出一种从丙炔醇高效且便捷构建螺[茚并苯并噻唑]骨架的方法。该反应在路易斯酸催化的级联过程中进行，包括烯丙基碳正离子与磺酰胺的捕获、亲电环化和分子内傅克烷基化。在 NIS 或 NBS 的存在下，可以以优异的收率制备碘代/溴代取代的螺[茚并苯并噻唑]。
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