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. 2008 Sep-Oct;10(5):658-63.
doi: 10.1021/cc800055x. Epub 2008 Aug 1.

Solution phase synthesis of a diverse library of highly substituted isoxazoles

Jesse P Waldo  1 , Saurabh Mehta, Benjamin Neuenswander, Gerald H Lushington, Richard C Larock
Affiliations

Solution phase synthesis of a diverse library of highly substituted isoxazoles

Jesse P Waldo et al. J Comb Chem. 2008 Sep-Oct.

Abstract

The iodocyclization of O-methyloximes of 2-alkyn-1-ones affords 4-iodoisoxazoles, which undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles. The palladium-catalyzed processes have been adapted to parallel synthesis utilizing commercially available boronic acid, acetylene, styrene, and amine sublibraries. Accordingly, a diverse 51-member library of 3,4,5-trisubstituted isoxazoles has been generated.

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Figures

Figure 1
Figure 1
4-Iodoisoxazole sublibrary.
Figure 2
Figure 2
Terminal acetylene sublibrary.
Figure 3
Figure 3
Styrene sublibrary.
Figure 4
Figure 4
Boronic acid sublibrary.
Figure 5
Figure 5
Primary amine sublibrary.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
See this image and copyright information in PMC

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