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Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides

Zeng-Yang He, Chao-Fan Huang and Shi-Kai Tian*

*Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email:

Z.-Y. He, C.-F. Huang, S.-K. Tian, Org. Lett., 2017, 19, 4850-4853.

DOI: 10.1021/acs.orglett.7b02312

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A copper/acid-catalyzed oxidative carbamoylation of various electron-deficient nitrogen heteroarenes (isoquinolines, quinolines, pyridines, phenanthridines, quinoxalines, and phthalazines) with hydrazinecarboxamide hydrochlorides provides structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields.

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proposed mechanism

Key Words

isoquinolines, tert-Butyl hydroperoxide

ID: J54-Y2017