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 language | English (US) |
|---|---|
| Pages (from-to) | 521-525 |
| Number of pages | 5 |
| Journal | Journal of Combinatorial Chemistry |
| Volume | 10 |
| Issue number | 4 |
| DOIs | |
| State | Published - Jul 2008 |
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ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
- Chemistry(all)
- Discrete Mathematics and Combinatorics
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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 journal › Article
}
TY - JOUR
T1 - Synthesis of 5-(thiazol-5-yl)-4,5-dihydroisoxazoles from 3-chloropentane-2,4-dione
AU - Milinkevich, Kristin A.
AU - Ye, Long
AU - Kurth, Mark J.
PY - 2008/7
Y1 - 2008/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=49049086496&partnerID=8YFLogxK
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U2 - 10.1021/cc800033m
DO - 10.1021/cc800033m
M3 - Article
C2 - 18505299
AN - SCOPUS:49049086496
VL - 10
SP - 521
EP - 525
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
SN - 2156-8952
IS - 4
ER -