Regio- and stereoselective synthesis of isoindolin-1-ones via electrophilic cyclization.
Regio- and stereoselective synthesis of isoindolin-1-ones via electrophilic cyclization.
复制标题
DOI：
10.1021/jo048007c
复制
发表时间：
2005-01
期刊：
影响因子：
--
通讯作者：
T. Yao;R. Larock
中科院分区：
文献类型：
--
作者：
T. Yao;R. Larock
[反应：见正文] 通过邻-(1-炔基)苯甲酰胺与 ICl、I(2) 和 NBS 的反应，可以在非常温和的反应条件下以良好至优异的收率轻松制备各种取代的异吲哚啉-1-酮。在少数情况下，取代的异喹啉-1-酮被作为主要产物获得。该方法适用于各种炔基酰胺和官能团，并已成功扩展到杂环起始材料。这种化学反应已成功应用于合成一种具有生物学意义的生物碱——cepharanone B。
[reaction: see text] A variety of substituted isoindolin-1-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICl, I(2), and NBS. In a few cases, substituted isoquinolin-1-ones were obtained as the major product instead. This methodology accommodates various alkynyl amides and functional groups and has been successfully extended to heterocyclic starting materials. This chemistry has been successfully applied to the synthesis of a biologically interesting alkaloid, cepharanone B.