The Synthesis of Five-Membered N-Heterocycles by Cycloaddition of Nitroalkenes with (In)Organic Azides and Other 1,3-Dipoles

Shandev Pookkandam Parambil; Santhini Pulikkal Veettil; Wim Dehaen

doi:10.1055/a-1547-0196

Synthesis 2022; 54(04): 910-924
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

Shandev Pookkandam Parambil‡

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

^bDepartment of Applied Chemistry, Cochin University of Science and Technology, Kerala 682022, India

,

Santhini Pulikkal Veettil‡

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

,

Wim Dehaen ∗

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

› Institutsangaben

Abstract

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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 - pyrazoles

Volltext

Referenzen

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