Organic Chemistry , Bergische Universität Wuppertal , Gaußstr. 20 , 42119 Wuppertal , Germany.
Org Lett. 2018 Nov 16;20(22):7066-7070. doi: 10.1021/acs.orglett.8b03013. Epub 2018 Oct 26.
The synthesis of previously unknown 3,3-diazidooxindoles as synthetically useful derivatives of isatins was accomplished through the direct oxidative diazidation of 2-oxindoles. The method yielded the diazido compounds from the starting oxindoles under mild and simple conditions with NaN and iodine, in good yields. The notable reactivity of this new class of compounds toward primary and secondary nucleophilic amines is also described, which gives access to either 4-imino-3,4-dihydroquinazolin-2(1 H)-one derivatives or cyanophenylureas.
通过 2-氧代吲哚的直接氧化重氮化，合成了以前未知的 3,3-二叠氮基氧吲哚，作为色满酮的有用合成衍生物。该方法在温和、简单的条件下，使用NaN 和碘，从起始的氧吲哚中以良好的产率得到了二氮化合物。还描述了这类新化合物与伯和仲亲核胺的显著反应性，这使得可以得到 4-亚氨基-3,4-二氢喹唑啉-2(1H)-酮衍生物或氰基苯脲。
