Improved synthesis of 3-aryl isoxazoles containing fused aromatic rings

Yousef R. Mirzaei; Matthew J. Weaver; Scott A. Steiger; Alison K. Kearns; Mariusz P. Gajewski; Kevin C. Rider; Howard D. Beall; N. R. Natale

doi:10.1016/j.tet.2012.09.084

Improved synthesis of 3-aryl isoxazoles containing fused aromatic rings

Yousef R. Mirzaei, Matthew J. Weaver, Scott A. Steiger, Alison K. Kearns, Mariusz P. Gajewski, Kevin C. Rider, Howard D. Beall, N. R. Natale

University of Montana

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

12 Scopus citations

Abstract

A critical comparison of methods to prepare sterically hindered 3-aryl isoxazoles containing fused aromatic rings using the nitrile oxide cycloaddition (NOC) reveal that modification of the method of Bode, Hachisu, Matsuura, and Suzuki (BHMS), utilizing either triethylamine as base or sodium enolates of the diketone, ketoester, and ketoamide dipolarophiles, respectively, was the method of choice for this transformation.

Original language	English
Pages (from-to)	10360-10364
Number of pages	5
Journal	Tetrahedron
Volume	68
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2012.09.084
State	Published - Dec 16 2012

Funding

The authors thank the NIH for grants R21NS067466 , P20RR017670 and P30NS055022 for financial support of this work.

Funder number
R21NS067466, P30NS055022, P20RR017670

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10.1016/j.tet.2012.09.084

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title = "Improved synthesis of 3-aryl isoxazoles containing fused aromatic rings",

abstract = "A critical comparison of methods to prepare sterically hindered 3-aryl isoxazoles containing fused aromatic rings using the nitrile oxide cycloaddition (NOC) reveal that modification of the method of Bode, Hachisu, Matsuura, and Suzuki (BHMS), utilizing either triethylamine as base or sodium enolates of the diketone, ketoester, and ketoamide dipolarophiles, respectively, was the method of choice for this transformation.",

author = "Mirzaei, \{Yousef R.\} and Weaver, \{Matthew J.\} and Steiger, \{Scott A.\} and Kearns, \{Alison K.\} and Gajewski, \{Mariusz P.\} and Rider, \{Kevin C.\} and Beall, \{Howard D.\} and Natale, \{N. R.\}",

note = "Funding Information: The authors thank the NIH for grants R21NS067466 , P20RR017670 and P30NS055022 for financial support of this work. ",

year = "2012",

month = dec,

day = "16",

doi = "10.1016/j.tet.2012.09.084",

language = "English",

volume = "68",

pages = "10360--10364",

journal = "Tetrahedron",

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T1 - Improved synthesis of 3-aryl isoxazoles containing fused aromatic rings

AU - Mirzaei, Yousef R.

AU - Weaver, Matthew J.

AU - Steiger, Scott A.

AU - Kearns, Alison K.

AU - Gajewski, Mariusz P.

AU - Rider, Kevin C.

AU - Beall, Howard D.

AU - Natale, N. R.

N1 - Funding Information: The authors thank the NIH for grants R21NS067466 , P20RR017670 and P30NS055022 for financial support of this work.

PY - 2012/12/16

Y1 - 2012/12/16

N2 - A critical comparison of methods to prepare sterically hindered 3-aryl isoxazoles containing fused aromatic rings using the nitrile oxide cycloaddition (NOC) reveal that modification of the method of Bode, Hachisu, Matsuura, and Suzuki (BHMS), utilizing either triethylamine as base or sodium enolates of the diketone, ketoester, and ketoamide dipolarophiles, respectively, was the method of choice for this transformation.

AB - A critical comparison of methods to prepare sterically hindered 3-aryl isoxazoles containing fused aromatic rings using the nitrile oxide cycloaddition (NOC) reveal that modification of the method of Bode, Hachisu, Matsuura, and Suzuki (BHMS), utilizing either triethylamine as base or sodium enolates of the diketone, ketoester, and ketoamide dipolarophiles, respectively, was the method of choice for this transformation.

UR - https://www.scopus.com/pages/publications/84869082878

U2 - 10.1016/j.tet.2012.09.084

DO - 10.1016/j.tet.2012.09.084

M3 - Article

AN - SCOPUS:84869082878

SN - 0040-4020

VL - 68

SP - 10360

EP - 10364

JO - Tetrahedron

JF - Tetrahedron

IS - 50

ER -

Improved synthesis of 3-aryl isoxazoles containing fused aromatic rings

Abstract

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