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

Research output: Contribution to journal › Article

6 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)10875-10882
Number of pages8
JournalJournal of Organic Chemistry
Volume82
Issue number20
DOIs
StatePublished - Oct 20 2017

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Isoxazoles
anthranil

ASJC Scopus subject areas

  • Organic Chemistry

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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

Diverting Reactive Intermediates Toward Unusual Chemistry : Unexpected Anthranil Products from Davis-Beirut Reaction. / Zhu, Jie S.; Son, Jung Ho; Teuthorn, Andrew P.; Haddadin, Makhluf J.; Kurth, Mark J.; Tantillo, Dean J.

In: Journal of Organic Chemistry, Vol. 82, No. 20, 20.10.2017, p. 10875-10882.

Research output: Contribution to journal › Article

Zhu, JS, Son, JH, Teuthorn, AP, Haddadin, MJ, Kurth, MJ & Tantillo, DJ 2017, 'Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction', Journal of Organic Chemistry, vol. 82, no. 20, pp. 10875-10882. https://doi.org/10.1021/acs.joc.7b01521
Zhu JS, Son JH, Teuthorn AP, Haddadin MJ, Kurth MJ, Tantillo DJ. Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction. Journal of Organic Chemistry. 2017 Oct 20;82(20):10875-10882. https://doi.org/10.1021/acs.joc.7b01521
Zhu, Jie S. ; Son, Jung Ho ; Teuthorn, Andrew P. ; Haddadin, Makhluf J. ; Kurth, Mark J. ; Tantillo, Dean J. / Diverting Reactive Intermediates Toward Unusual Chemistry : Unexpected Anthranil Products from Davis-Beirut Reaction. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 20. pp. 10875-10882.
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