Issue 4, 2022

Generation of azaarene nitrile oxides from methyl azaarenes and t-BuONO enabling the synthesis of furoxans and 1,2,4-oxadiazoles

Abstract

A high-efficiency strategy for the synthesis of furoxans and 1,2,4-oxadiazoles has been developed, using tert-butyl nitrite (TBN) as the nitrogen source. Azaarene nitrile oxides as activated intermediates were generated in situ via methyl azaarene functionalization. When the reaction used TBN as the NO source under mild conditions, the corresponding furoxans were obtained in high yields (up to 92%). Unexpectedly, 1,2,4-oxadiazole bearing two quinoline groups was obtained, when the reaction was carried out in EtOH. Further transformations from furoxans to multifunctional blasting materials furazans, structural modifications of natural products and a gram-scale reaction proved the potential applications of this method.

Graphical abstract: Generation of azaarene nitrile oxides from methyl azaarenes and t-BuONO enabling the synthesis of furoxans and 1,2,4-oxadiazoles

Supplementary files

Article information

Article type
Research Article
Submitted
15 Dec 2021
Accepted
12 Jan 2022
First published
13 Jan 2022

Org. Chem. Front., 2022,9, 1121-1126

Generation of azaarene nitrile oxides from methyl azaarenes and t-BuONO enabling the synthesis of furoxans and 1,2,4-oxadiazoles

X. Zhang, J. Cao, J. Ren, L. Hong, R. Liang, K. Hao, K. Wei, B. Mi, Y. Liu and Y. Zhu, Org. Chem. Front., 2022, 9, 1121 DOI: 10.1039/D1QO01872H

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