State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
J Org Chem. 2017 Mar 17;82(6):3232-3238. doi: 10.1021/acs.joc.6b02774. Epub 2017 Mar 3.
An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.
在简单碱介导条件下，实现了 3-（羟亚氨基）吲哚啉-2-酮与二芳基碘鎓盐的高效选择性 N-芳基化反应，制备（Z）-N-芳基氧化吲哚硝酮。该反应可耐受具有各种不同和敏感官能团的多种二芳基碘鎓盐。对肟结构的研究表明，3-（羟亚氨基）吲哚啉-2-酮中的吡咯烷环和羰基在选择性 N-芳基化过程中起着重要作用。N-芳基氧化吲哚硝酮可以快速、简便地在克级规模制备。
