Synthesis of 5-(thiazol-5-yl)-4,5-dihydroisoxazoles from 3-chloropentane-2,4-dione

Kristin A. Milinkevich, Long Ye, Mark J. Kurth

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Condensation of 3-chloropentane-2,4-dione with thioamides gives 1-(thiazol-5-yl)ethanones and subsequent Wittig olefination, followed by nitrile oxide 1,3-dipolar cycloaddition to the resulting prop-1-en-2-yl moiety, delivers racemic 5-(thiazol-5-yl)-4,5-dihydroisoxazoles. When this thiazole and isoxazoline diheterocyclic scaffold has a carboethoxy substituent at C2 of the thiazole ring, aminolysis provides for effective diversification. A 50-member library of various 5-(thiazol-5-yl)-4,5-dihydroisoxazoles is reported.

Original languageEnglish (US)
Pages (from-to)521-525
Number of pages5
JournalJournal of Combinatorial Chemistry
Volume10
Issue number4
DOIs
StatePublished - Jul 2008

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Thiazoles
Scaffold
Diversification
Condensation
Oxides
Thioamides
Synthesis
Ring
Nitriles
Cycloaddition
Cycloaddition Reaction
Scaffolds
Libraries
3-chloropentane-2,4-dione

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

Cite this

Synthesis of 5-(thiazol-5-yl)-4,5-dihydroisoxazoles from 3-chloropentane-2,4-dione. / Milinkevich, Kristin A.; Ye, Long; Kurth, Mark J.

In: Journal of Combinatorial Chemistry, Vol. 10, No. 4, 07.2008, p. 521-525.

Research output: Contribution to journalArticle

Milinkevich, Kristin A. ; Ye, Long ; Kurth, Mark J. / Synthesis of 5-(thiazol-5-yl)-4,5-dihydroisoxazoles from 3-chloropentane-2,4-dione. In: Journal of Combinatorial Chemistry. 2008 ; Vol. 10, No. 4. pp. 521-525.
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