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 › peer-review

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

Access to Document

10.1021/acs.joc.7b01521

Fingerprint Dive into the research topics of 'Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction'. Together they form a unique fingerprint.

Cite this

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 › peer-review

@article{b2b77ae277d44d05a52411e87dd0bc89,

title = "Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction",

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.",

author = "Zhu, {Jie S.} and Son, {Jung Ho} and Teuthorn, {Andrew P.} and Haddadin, {Makhluf J.} and Kurth, {Mark J.} and Tantillo, {Dean J.}",

year = "2017",

month = oct,

day = "20",

doi = "10.1021/acs.joc.7b01521",

language = "English (US)",

volume = "82",

pages = "10875--10882",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Diverting Reactive Intermediates Toward Unusual Chemistry

T2 - Unexpected Anthranil Products from Davis-Beirut Reaction

AU - Zhu, Jie S.

AU - Son, Jung Ho

AU - Teuthorn, Andrew P.

AU - Haddadin, Makhluf J.

AU - Kurth, Mark J.

AU - Tantillo, Dean J.

PY - 2017/10/20

Y1 - 2017/10/20

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85031931781&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85031931781&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.7b01521

DO - 10.1021/acs.joc.7b01521

M3 - Article

AN - SCOPUS:85031931781

VL - 82

SP - 10875

EP - 10882

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 20

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this