A Cobalt Mediated Nitrene Transfer <i>aza</i>-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds
作者:Daniël S. Verdoorn、Prabhat Ranjan、Tim de Reuver、Elwin Janssen、Christophe M. L. Vande Velde、Jordy M. Saya、Bert U. W. Maes、Romano V. A. Orru
DOI:10.1021/acs.orglett.3c00959
日期:2023.6.9
A cobalt(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imines using sulfonyl azides, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig
使用磺酰叠氮化物、 N-异氰亚氨基三苯基正膦 (NIITP) 和羧酸,钴 (II) 介导的 5-取代-N-磺酰基-1,3,4-恶二唑-2(3 H )-亚胺的三组分合成已被报道发达。这种一锅串联反应首先将氮烯转移到 NIITP,然后将羧酸添加到原位形成的碳二亚胺中,然后进行分子内氮杂维蒂希反应。羧酸的空间限制和所用钴盐的化学计量决定了两种产物的选择性,即5-取代-N-磺酰基-1,3,4-恶二唑-2( 3H )-亚胺与5-取代-N-磺酰基-1,3,4-恶二唑-2(3H)-亚胺。取代的-4-甲苯磺酰基-2,4-二氢-3H -1,2,4-三唑-3-酮。