DBU mediated coupling of isatin with phenacyl azides: synthesis of 2-oxoindolin-3-ylbenzoates?
New Journal of Chemistry Pub Date: 2022-12-28 DOI: 10.1039/D2NJ05661E
Abstract
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) catalyzed redox neutral coupling of isatin with phenacyl azides in acetonitrile to yield 2-oxoindolin-3-yl benzoates under mild reaction conditions was developed. The scope of the reaction that leads to the formation of a new C–O and C–H bond in the overall transformation was explored by synthesizing more than 35 examples in high yields (70–85%). Un-substituted phenacyl azides as well as those bearing electron donating groups (Me, OMe, OH, OCH2O), halogen atoms (Cl, Br) or electron withdrawing group (CN, NO2) led to the reductive aroylation of isatin in high yields in a short reaction time (6 h).
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Journal Name：New Journal of Chemistry
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CAS no.: 89640-58-4
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