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Synthesis 2022; 54(04): 910-924
DOI: 10.1055/a-1547-0196
DOI: 10.1055/a-1547-0196
special topic
Cycloadditions – Established and Novel Trends – in Celebration of the 70th Anniversary of the Nobel Prize Awarded to Otto Diels and Kurt Alder
The Synthesis of Five-Membered N-Heterocycles by Cycloaddition of Nitroalkenes with (In)Organic Azides and Other 1,3-Dipoles
W.D. acknowledges financial support from Fonds Wetenschappelijk Onderzoek, KU Leuven (grant C14/19/78).
Abstract
Cycloaddition reactions have emerged as rapid and powerful methods for constructing heterocycles and carbocycles. [3+2] Cycloadditions of nitroalkenes with various 1,3-dipoles have been an interesting research area for many organic chemists. This review outlines the synthesis of N-substituted and NH-1,2,3-triazoles along with other five-membered N-heterocycles through cycloaddition reactions of nitroalkenes.
1 Introduction
2 Synthesis of 1,2,3-Triazoles
2.1 Synthesis of NH-1,2,3-Triazoles
2.2 Synthesis of N-Substituted 1,2,3-Triazoles
3 Synthesis of Pyrrolidines and Pyrroles
4 Synthesis of Pyrazoles
5 Conclusion
Key words
nitroalkenes - 1,3-dipolar cycloaddition - azides - triazoles - pyrrolidines - pyrroles - pyrazolesPublication History
Received: 31 May 2021
Accepted after revision: 09 July 2021
Accepted Manuscript online:
09 July 2021
Article published online:
19 August 2021
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