3 years ago

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

One-Pot Synthesis
of Benzo[b][1,4]oxazins via Intramolecular
Trapping Iminoenol
Yadong Feng, Jinhai Shen, Guolin Cheng, Hong Zhang, Xiuling Cui
A highly atom-efficient “one-pot” protocol has been developed to construct multisubstituted 2-hydroxy-benzo[b][1,4]oxazins starting from N-(2-hydroxylaryl)enaminones. This procedure comprises a PIDA-mediated intramolecular iminoenol tautomer trapping reaction, followed by Et3N-promoted aerobic oxidative ring construction. In particular, an O2 molecule from air served as the oxygen source of the hydroxyl group in the titled products. This reaction proceeded smoothly at room temperature under air atmosphere and metal-free conditions.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03804

DOI: 10.1021/acs.orglett.7b03804

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