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Synthesis 2021; 53(20): 3673-3682
DOI: 10.1055/a-1529-7678
DOI: 10.1055/a-1529-7678
short review
Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity
This research was supported by the Ministry of Science and Higher Education of the Russian Federation (agreement with the N.D. Zelinsky Institute of Organic Chemistry, RAS no. 075-15-2020-803).
Abstract
Five-membered heterocyclic N-oxides attract special attention due to their significant potential applications in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are in constant demand. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are summarized. The main routes involving transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. The transformations of these hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.
1 Introduction
2 Isoxazoline N-Oxides
3 1,2,3-Triazole 1-Oxides
4 1,2,5-Oxadiazole 2-Oxides
5 Conclusion
Key words
nitrogen heterocycles - isoxazolines - 1,2,3-triazoles - 1,2,5-oxadiazoles - C–H functionalization - ring cleavage - cycloadditionPublication History
Received: 08 May 2021
Accepted after revision: 16 June 2021
Accepted Manuscript online:
16 June 2021
Article published online:
05 August 2021
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