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Hetero-Tetradehydro-Diels-Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines

Nikolay V. Shcherbakov, Dmitry V. Dar'in, Vadim Yu. Kukushkin* and Alexey Yu. Dubovtsev*

*Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation, Email: v.kukushkinspbu.ru, a.dubovtsevspbu.ru

N. V. Shcherbakov, D. V. Dar'in, Y. Y. Kukushkin, Y. Y. Dubovtsev, J. Org. Chem., 2021, 86, 7218-7228.

DOI: 10.1021/acs.joc.1c00558


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Abstract

A Gold(I)-catalyzed hetero-tetradehydro-Diels-Alder cycloaddition of enynamides and cyanamides provides diversely substituted 2,6-diaminopyridines in very good yields. This efficient reaction proceeds under very mild conditions with high functional group tolerance.


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proposed mechanism



Key Words

pyridines


ID: J42-Y2021