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One-Pot Synthesis of Benzo[b][1,4]oxazins via Intramolecular Trapping Iminoenol

Hong Zhang, Jinhai Shen, Guolin Cheng, Yadong Feng and Xiuling Cui*

*School of Biomedical Sciences, Huaqiao University, Xiamen 361021, P. R. China, Email:

H. Zhang, J. Shen, G. Cheng, Y. Feng, X. Cui, Org. Lett., 2018, 20, 664-667.

DOI: 10.1021/acs.orglett.7b03804

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A highly atom-efficient PIDA-mediated intramolecular iminoenol tautomer trapping reaction, followed by Et3N-promoted aerobic oxidative ring construction enables the synthesis of multisubstituted 2-hydroxy-benzo[b][1,4]oxazins from N-(2-hydroxylaryl)enaminones at room temperature under air. O2 serves as the oxygen source of the hydroxyl group.

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proposed mechanism

Key Words

benzo-fused N-heterocycles, benzo-fused O-heterocycles, oxygen, PIDA

ID: J54-Y2018