A novel protocol for ionic liquid (IL)-mediated C(sp3)–H bond functionalization of 3,5-dimethyl-4-nitroisoxazoles 4 to substituted o-amino benzaldehydes 5 was developed in excellent yields. Isoxazolyl aryl ethanones 7 have been synthesized from isoxazolyl aryl ethanol synthon 6. Furthermore, utilizing the later as synthons for IL promoted Friedlander synthesis of highly functionalized isoxazole substituted quinoline libraries 9. The merit of this synthesis is easily available and economical starting materials, effective utilization of all the reactants, and simple workup procedure. It is noteworthy that ionic liquid used in C(sp3)–H bond functionalization and Friedlander synthesis reactions can be recycled and reused five times without significant decrease in activity.
Journal of the Iranian Chemical Society – Springer Journals
Published: May 28, 2018
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