A three-component approach to isoxazolines and isoxazoles under metal-free conditions

Dahan Wang; Feng Zhang; Fuhong Xiao; Guo-Jun Deng

doi:10.1039/C9OB01909J

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A three-component approach to isoxazolines and isoxazoles under metal-free conditions†

Dahan Wang,^a Feng Zhang,^b Fuhong Xiao

*^a and Guo-Jun Deng

*^a

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* Corresponding authors

^a Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Key Laboratory for Green Organic Synthesis and Application of Hunan. Province, College of Chemistry, Xiangtan University, Xiangtan 411105, China
E-mail: fhxiao@xtu.edu.cn, gjdeng@xtu.edu.cn

^b College of Science, Hunan Agricultural University, Changsha 410128, China

Abstract

A 1,3-dipolar cycloaddition of 2-methylquinoline, tert-butyl nitrite (TBN) and alkynes or alkenes for the synthesis of biheteroaryls containing both isoxazoline/isoxazole and quinoline motifs has been developed. In this protocol, TBN serves as a convenient N–O source to convert 2-methylquinoline into intermediate nitrile oxides in situ.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB01909J
Article type: Paper
Submitted: 31 Aug 2019
Accepted: 01 Oct 2019
First published: 02 Oct 2019

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Org. Biomol. Chem., 2019,17, 9163-9168

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A three-component approach to isoxazolines and isoxazoles under metal-free conditions

D. Wang, F. Zhang, F. Xiao and G. Deng, Org. Biomol. Chem., 2019, 17, 9163 DOI: 10.1039/C9OB01909J

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Organic & Biomolecular Chemistry

A three-component approach to isoxazolines and isoxazoles under metal-free conditions†

Abstract

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A three-component approach to isoxazolines and isoxazoles under metal-free conditions

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