Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskiye Gory 1, Moscow 119991, Russia.
Department of Chemistry, Korea Advanced Institute of Science and Technology, Daejeon 34141, Republic of Korea.
J Org Chem. 2020 Jul 17;85(14):9015-9028. doi: 10.1021/acs.joc.0c00931. Epub 2020 Jun 26.
An efficient cascade approach to thiosubstituted benzoxazoles has been developed. The transformation starts with generation of a diazo compound via annulation-triggered electrocyclic opening of the 1,2,3-triazole ring. The subsequent Cu-catalyzed trapping of diazo intermediates by various thiols affords the desired heterocycles in generally good yields of up to 91%. The protocol features very good functional group tolerance and is applicable to substrates with different electronic properties.
一种高效的噻取代苯并恶唑的级联方法已经被开发出来。该转化从通过 1,2,3-三唑环的环加成引发的电环开环生成重氮化合物开始。随后，各种硫醇通过 Cu 催化捕获重氮中间体，通常以高达 91%的产率得到所需的杂环。该方案具有非常好的官能团耐受性，并且适用于具有不同电子性质的底物。
