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Synthesis of optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole rings


Wroblewska, Aneta; Mloston, Grzegorz; Heimgartner, Heinz (2015). Synthesis of optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole rings. Tetrahedron: Asymmetry, 26(34):1448-1452.

Abstract

Optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole units were obtained via a multistep synthesis with the [3+2] cycloaddition of Boc-protected (S)-(pyrrolidin-2-yl)methyl azide with 2-ethynylimidazoles in the presence of CuI (CuAAC reaction) as the key step. Typical for terminal alkynes, the reactions occurred regioselectively and 1,4-disubstituted 1,2,3-triazoles were formed exclusively. The deprotection of the pyrrolidine N-atom was performed by treatment with TFA under standard conditions.

Abstract

Optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole units were obtained via a multistep synthesis with the [3+2] cycloaddition of Boc-protected (S)-(pyrrolidin-2-yl)methyl azide with 2-ethynylimidazoles in the presence of CuI (CuAAC reaction) as the key step. Typical for terminal alkynes, the reactions occurred regioselectively and 1,4-disubstituted 1,2,3-triazoles were formed exclusively. The deprotection of the pyrrolidine N-atom was performed by treatment with TFA under standard conditions.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:31 December 2015
Deposited On:08 Dec 2015 15:53
Last Modified:08 Dec 2017 15:30
Publisher:Elsevier
ISSN:0957-4166
Funders:National Science Center (Cracow), Foundation of the University of Lodz
Publisher DOI:https://doi.org/10.1016/j.tetasy.2015.10.019

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