Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

Cindy C. Browder; Christopher B. Moss; Matthew B. Kraft; Paige L. Petrucka; Tara S. Morey; Christopher W. Leach; Nicholas C. Gearhart

doi:10.2174/157017811795371476

Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

Cindy C. Browder
, Christopher B. Moss
, Matthew B. Kraft
, Paige L. Petrucka
, Tara S. Morey
, Christopher W. Leach
, Nicholas C. Gearhart

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

Abstract

An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.

Original language	English (US)
Pages (from-to)	229-233
Number of pages	5
Journal	Letters in Organic Chemistry
Volume	8
Issue number	4
DOIs	https://doi.org/10.2174/157017811795371476
State	Published - May 2011

Keywords

Copper-mediated
Cyclization
Isoxazole

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

Access to Document

10.2174/157017811795371476

Cite this

@article{3a53e5144f454a2aabd186e862b4db21,

title = "Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles",

abstract = "An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.",

keywords = "Copper-mediated, Cyclization, Isoxazole",

author = "Browder, \{Cindy C.\} and Moss, \{Christopher B.\} and Kraft, \{Matthew B.\} and Petrucka, \{Paige L.\} and Morey, \{Tara S.\} and Leach, \{Christopher W.\} and Gearhart, \{Nicholas C.\}",

year = "2011",

month = may,

doi = "10.2174/157017811795371476",

language = "English (US)",

volume = "8",

pages = "229--233",

journal = "Letters in Organic Chemistry",

issn = "1570-1786",

publisher = "Bentham Science Publishers",

number = "4",

}

TY - JOUR

T1 - Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

AU - Browder, Cindy C.

AU - Moss, Christopher B.

AU - Kraft, Matthew B.

AU - Petrucka, Paige L.

AU - Morey, Tara S.

AU - Leach, Christopher W.

AU - Gearhart, Nicholas C.

PY - 2011/5

Y1 - 2011/5

N2 - An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.

AB - An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.

KW - Copper-mediated

KW - Cyclization

KW - Isoxazole

UR - https://www.scopus.com/pages/publications/79954472523

UR - https://www.scopus.com/pages/publications/79954472523#tab=citedBy

U2 - 10.2174/157017811795371476

DO - 10.2174/157017811795371476

M3 - Article

AN - SCOPUS:79954472523

SN - 1570-1786

VL - 8

SP - 229

EP - 233

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 4

ER -

Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this