N₂H₄-H₂O Enabled Umpolung Cyclization of o-Nitro Chalcones for the Construction of Quinoline N-Oxides

Guan Zhang, Kai Yang, Shihui Wang, Qiang Feng and Qiuling Song*

*College of Chemical Engineering, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, P. R. China, Email: qsonghqu.edu.cn

G. Zhang, K. Yang, S. Wang, Q. Feng, Q. Song, Org. Lett., 2021, 23, 595-600.

DOI: 10.1021/acs.orglett.0c04162

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Abstract

The use of hydrazine under basic conditions enables an efficient and general construction of quinoline N-oxides from ortho-nitro chalcones via umpolung of carbonyl groups. This transition-metal free method offers good functional group tolerance, environmental friendliness, and mild reaction conditions with nitrogen gas as byproduct.

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Key Words

quinolines, hydrazine

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ID: J54-Y2021