Solid-Phase Synthesis of Isoxazoles and Isoxazolines

En Route to a New Class of Ionophores

Eric J. Kantorowski, Mark J. Kurth

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

Solid-phase organic synthesis (SPOS) was employed in the construction of isoxazole and/or isoxazoline polyheterocyclic systems. The [3 + 2] cycloaddition reactions of nitrile oxides generated from the corresponding primary nitro compounds, with resin-bound alkynes or alkenes were highly efficient both chemically and with regard to purification. A parallel solution-phase synthesis was carried out which compared the synthetic efficiency in both media. SPOS of isoxazole/isoxazoline 11, employing a functionalized polystyrene resin, was found to be more efficient than the solution-phase approach. Three other oligoisoxazoles were prepared with average yields per step being 82, 84, and 89%.

Original languageEnglish (US)
Pages (from-to)6797-6803
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number20
StatePublished - 1997

Fingerprint

Isoxazoles
Ionophores
Resins
Nitro Compounds
Nitriles
Alkynes
Cycloaddition
Polystyrenes
Alkenes
Oxides
Purification

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Solid-Phase Synthesis of Isoxazoles and Isoxazolines : En Route to a New Class of Ionophores. / Kantorowski, Eric J.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 62, No. 20, 1997, p. 6797-6803.

Research output: Contribution to journalArticle

Kantorowski, Eric J. ; Kurth, Mark J. / Solid-Phase Synthesis of Isoxazoles and Isoxazolines : En Route to a New Class of Ionophores. In: Journal of Organic Chemistry. 1997 ; Vol. 62, No. 20. pp. 6797-6803.
@article{984c5712fcea456b9461fb7c5a089beb,
title = "Solid-Phase Synthesis of Isoxazoles and Isoxazolines: En Route to a New Class of Ionophores",
abstract = "Solid-phase organic synthesis (SPOS) was employed in the construction of isoxazole and/or isoxazoline polyheterocyclic systems. The [3 + 2] cycloaddition reactions of nitrile oxides generated from the corresponding primary nitro compounds, with resin-bound alkynes or alkenes were highly efficient both chemically and with regard to purification. A parallel solution-phase synthesis was carried out which compared the synthetic efficiency in both media. SPOS of isoxazole/isoxazoline 11, employing a functionalized polystyrene resin, was found to be more efficient than the solution-phase approach. Three other oligoisoxazoles were prepared with average yields per step being 82, 84, and 89{\%}.",
author = "Kantorowski, {Eric J.} and Kurth, {Mark J.}",
year = "1997",
language = "English (US)",
volume = "62",
pages = "6797--6803",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "20",

}

TY - JOUR

T1 - Solid-Phase Synthesis of Isoxazoles and Isoxazolines

T2 - En Route to a New Class of Ionophores

AU - Kantorowski, Eric J.

AU - Kurth, Mark J.

PY - 1997

Y1 - 1997

N2 - Solid-phase organic synthesis (SPOS) was employed in the construction of isoxazole and/or isoxazoline polyheterocyclic systems. The [3 + 2] cycloaddition reactions of nitrile oxides generated from the corresponding primary nitro compounds, with resin-bound alkynes or alkenes were highly efficient both chemically and with regard to purification. A parallel solution-phase synthesis was carried out which compared the synthetic efficiency in both media. SPOS of isoxazole/isoxazoline 11, employing a functionalized polystyrene resin, was found to be more efficient than the solution-phase approach. Three other oligoisoxazoles were prepared with average yields per step being 82, 84, and 89%.

AB - Solid-phase organic synthesis (SPOS) was employed in the construction of isoxazole and/or isoxazoline polyheterocyclic systems. The [3 + 2] cycloaddition reactions of nitrile oxides generated from the corresponding primary nitro compounds, with resin-bound alkynes or alkenes were highly efficient both chemically and with regard to purification. A parallel solution-phase synthesis was carried out which compared the synthetic efficiency in both media. SPOS of isoxazole/isoxazoline 11, employing a functionalized polystyrene resin, was found to be more efficient than the solution-phase approach. Three other oligoisoxazoles were prepared with average yields per step being 82, 84, and 89%.

UR - http://www.scopus.com/inward/record.url?scp=0004077149&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0004077149&partnerID=8YFLogxK

M3 - Article

VL - 62

SP - 6797

EP - 6803

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 20

ER -