Synthesis of 5-(thiazol-5-yl)-4,5-dihydroisoxazoles from 3-chloropentane-2,4-dione.
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.
Milinkevich
Kristin A
KA
Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616, USA.
Ye
Long
L
Kurth
Mark J
MJ
D017606:Chlorine Compounds / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010420:Pentanes / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
C531375:3-chloropentane-2,4-dione; D017606:Chlorine Compounds; D007555:Isoxazoles; D010420:Pentanes; D013438:Sulfhydryl Compounds; D006859:Hydrogen