Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process
Si-Yi Wu1, Xiao-Pan Ma1, Cui Liang1
1State 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.
Abstract:
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.
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