Patil Pravin C, Luzzio Frederick A
Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, Kentucky 40292, USA.
Synlett. 2017 Sep;28(14):1729-1732. doi: 10.1055/s-0036-1588510. Epub 2017 Jul 24.
A novel -butyl 2-(1-oxoisolndolin-2-yl)acetate derivative is selectively alkylated with propargyl bromide in the presence of lithium hexamethyldisilazide. After removal of the -butyl protecting group, the resulting -isoindolinyl (ethynylalanine) derivative is reacted with a series of azides under 'click conditions'. The click reactions afford an array of -isoindolinyl-1,2,3-triazolylalanine derivatives as the free carboxylic adds. Following esterification, the -isoindolinone protecting group is then transformed into the more easily removable phthaloyl group by selective oxidation at the benzylic position.
一种新型的2-(1-氧代异吲哚啉-2-基)乙酸叔丁酯衍生物在六甲基二硅基锂酰胺存在下与炔丙基溴进行选择性烷基化反应。在除去叔丁基保护基后，所得的异吲哚啉基（乙炔基丙氨酸）衍生物在“点击反应条件”下与一系列叠氮化物反应。点击反应得到一系列作为游离羧酸的异吲哚啉基-1,2,3-三唑基丙氨酸衍生物。酯化后，通过苄基位置的选择性氧化将异吲哚啉酮保护基转化为更易于除去的邻苯二甲酰基。
