tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes

The Journal of Organic Chemistry
Prasenjit SauBhisma K Patel

Abstract

A sequential construction of C-C, C-O, C═N, and C═O bonds from alkenes leading to the direct synthesis of isoxazolines in the presence of tert-butyl nitrite, quinoline, and the Sc(OTf)3 catalyst in DCE at 80 °C has been accomplished. An unprecedented three consecutive C-H functionalizations of two styrenes are involved in this isoxazoline synthesis. In this radical-mediated reaction, one-half of the aryl alkene is converted into an intermediate 2-nitroketone, which serves as a 1,3-dipolarophile and undergoes cycloaddition with the other half of the unreacted aromatic terminal alkene. The use of an alkyne in lieu of an alkene leads to the formation of isoxazole under identical reaction conditions.

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Citations

Nov 23, 2018·Organic & Biomolecular Chemistry· Preeti, Krishna Nand Singh
Oct 10, 2019·Organic & Biomolecular Chemistry·Dahan WangGuo-Jun Deng
Sep 21, 2019·Chemistry, an Asian Journal·Anjali DahiyaBhisma K Patel
May 18, 2021·European Journal of Medicinal Chemistry·Girish Chandra AryaVikas Jaitak

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