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

Jie S. Zhu; Jung Ho Son; Andrew P. Teuthorn; Makhluf J. Haddadin; Mark J. Kurth; Dean J. Tantillo

doi:10.1021/acs.joc.7b01521

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

Jie S. Zhu, Jung Ho Son, Andrew P. Teuthorn, Makhluf J. Haddadin, Mark J. Kurth, Dean J. Tantillo

Chemistry

Research output: Contribution to journal › Article

6 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	10875-10882
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	82
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.7b01521
State	Published - Oct 20 2017

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.7b01521

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Zhu, J. S., Son, J. H., Teuthorn, A. P., Haddadin, M. J., Kurth, M. J., & Tantillo, D. J. (2017). Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction. Journal of Organic Chemistry, 82(20), 10875-10882. https://doi.org/10.1021/acs.joc.7b01521

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