Synthesis of Sterically Protected Isoindoles from ortho-Phthalaldehyde.
Synthesis of Sterically Protected Isoindoles from ortho-Phthalaldehyde.
复制标题
从邻苯二醛合成空间保护的异吲哚。
作者：
Nakao M;Nishikiori N;Nakamura A;Miyagi M;Shibata;N;Kitaike S;Fukui M;Ito;H-O;Sano;S
邻苯二甲醛（OPA）与O-保护的三羟烷基氨基甲烷在1-丙硫醇存在下反应，得到一类新的稳定的异吲哚。由三（羟甲基）氨基甲烷衍生的C3-对称伯胺的大体积提供的空间保护对于由OPA衍生的1-烷硫基-2-烷基取代的异吲哚的稳定化可能是重要的。提出了一个合理的反应机理来解释异吲哚和异吲哚啉-1-酮副产物的形成。
o-Phthalaldehyde (OPA) reacts withO-protected tris(hydroxyalkyl)aminomethanes in the presence of 1-propanethiol to afford a novel class of stable isoindoles. Steric protection provided by the bulkiness ofC3-symmetric primary amines derived from tris(hydroxymethyl)aminomethane could be significant for the stabilization of 1-alkylthio-2-alkyl-substituted isoindoles derived from OPA. A plausible reaction mechanism is proposed to explain the formation of the isoindole and an isoindolin-1-one by-product.