A library of 3-aryl-4,5-dihydroisoxazole-5-carboxamides.
Parallel solution phase methods for the preparation of a 72-membered 3-aryl-4,5-dihydroisoxazole-5-carboxamide library is reported. The reaction order (nitrile oxide 1,3-dipolar cycloaddition followed by amide formation, or vice versa) was investigated both experimentally and computationally to determine which route would result in the highest yields, minimize purification efforts, and give higher 1,3-dipolar cycloaddition regioselectivity. Automated preparative HPLC was used to purify the final products to >or=90% purity on a 10+ mg scale.
Jeddeloh
Melissa R
MR
Department of Chemistry, University of California, 1 Shields Avenue, Davis, California 95616-5295, USA.
Holden
Jason B
JB
Nouri
Dustin H
DH
Kurth
Mark J
MJ
D000577:Amides / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D007555:Isoxazoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical
D000577:Amides; D007555:Isoxazoles