Liquid-phase synthesis of isoxazoles and isoxazolines through a 1,3-dipolar of nitrile oxides is described. Soluble polymer-supported nitrile oxides generated in situ react with dipolarophiles to afford isoxazoles and isoxazolines in good yields and purity.
(a) ThompsonL.A., and EllmanJ. A., Chem. Rev., 1996, 96, 555.
2.
DolleR.E., J. Comb. Chem., 2001, 3, 477.
3.
HanH., WolfeM. M., BrennerS., and JandaK. D., Proc. Natl. Acad. Sci. U.S.A., 1995, 92, 6419.
4.
(a) WentworthJ., and JandaK. D., Chem. Commun., 1999, 1917.
5.
GeekelerK.E., Adv. Polym. Sci., 1995, 121, 31.
6.
Reviews on liquid-phase organic synthesis (LPOS): (a) GravertD.J., and JandaK. D., Chem. Rev., 1997, 97, 489.
7.
HarwigC.W., GravertD. J., and JandaK. D., Chemtracts: Org. Chem., 1999, 12, 1.
8.
GravertD.J., and JandaK. D., In Molecular Diversity and Combinatorial Synthesis: Libraries and Drug Discovery; ChaikenI.M., and JandaK. D., eds, ACS Symp. Ser.; American Chemical Society: Washington, D C, 1996; 118.
9.
VandersteenA.M., HanH., and JandaK. D., Mol. Diversity, 1996, 2, 89.
ZhaoX.Y., MetzW. A., SieberF., and JandaK. D., Tetrahedron Lett., 1998, 39, 8433.
12.
ZhuJ., and HegedusL. S., J. Org. Chem., 1995, 60, 5831.
13.
BlaskovichM.A., and KahnM., J. Org. Chem., 1998, 63, 1119.
14.
A search in MDDR (MDL data base) revealed the presence of more than 250 structures based on the isoxazole scaffold and endowed with several pharmacological activities used for analgesia, inflammation, immunology and CNS diseases (such as anxiety, memory impairment, depression, Parkinson's and stroke).
15.
For the first example of a liquid-phase 1,3-dipolar cycloaddition reaction see MooreM., and NorrisP., Tetrahedron Lett., 1998, 39, 7027.
16.
(a) ShankarB.B., YangD. Y., GirtonS., and GangulyA. K., Tetrahedron Lett., 1998, 39, 2447.
17.
BatraS., RastogiS. K., KunduB., PatraA., and BhaduriA. P., Tetrahedron Lett., 2000, 41, 5971.
18.
LucaL.D., GiacomelliG., and RiuA., J. Org. Chem., 2001, 66, 6823.