3 years ago

Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis–Beirut Reaction

Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis–Beirut Reaction
Jung-Ho Son, Makhluf J. Haddadin, Andrew P. Teuthorn, Mark J. Kurth, Jie S. Zhu, Dean J. Tantillo
The discovery of a new variation on the Davis–Beirut reaction is described in which an atypical heterocyclic framework (the anthranil or benzo[c]isoxazole framework) is formed as the result of diversion of a key reactive intermediate away from its expected reactivity—a potentially general approach to reaction design and development. Experimental and computational support for the proposed mechanism and origins of altered reactivity are described.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01521

DOI: 10.1021/acs.joc.7b01521

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