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Synthesis and Selected Transformations of 2-Unsubstituted Imidazole N-Oxides Using a Ball-Milling Mechanochemical Approach


Mlostoń, Grzegorz; Celeda, Malgorzata; Heimgartner, Heinz; Duda, Damian; Obijalska, Emilia; Jasiński, Marcin (2022). Synthesis and Selected Transformations of 2-Unsubstituted Imidazole N-Oxides Using a Ball-Milling Mechanochemical Approach. Catalysts, 12:589.

Abstract

Synthetically relevant 2-unsubstituted imidazole N-oxides were obtained by using the ball-milling mechanochemical method. The presented approach extended the scope of the known method and enabled the preparation of hitherto little known N(1)-aryl-substituted derivatives, which are of interest as starting materials for the synthesis of more complex imidazole-based organic materials, generally in good to excellent yields. In addition, selected one-pot mechanochemical transformations including N- and O-alkylations as well as sulfur transfer reactions based on either (3+2)-cycloaddition reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione or sulfurization of the transient imidazol-2-ylidenes, generated from corresponding imidazolium salts, were studied. The reported results can be considered as a continuation of long-term studies focused on the synthesis and applications of 2-unsubstituted imidazole N-oxides.
Keywords: imidazole N-oxides; mechanochemistry; imidazolium salts; NHC carbenes; sulfur-transfer reactions; imidazole-2-thiones

Abstract

Synthetically relevant 2-unsubstituted imidazole N-oxides were obtained by using the ball-milling mechanochemical method. The presented approach extended the scope of the known method and enabled the preparation of hitherto little known N(1)-aryl-substituted derivatives, which are of interest as starting materials for the synthesis of more complex imidazole-based organic materials, generally in good to excellent yields. In addition, selected one-pot mechanochemical transformations including N- and O-alkylations as well as sulfur transfer reactions based on either (3+2)-cycloaddition reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione or sulfurization of the transient imidazol-2-ylidenes, generated from corresponding imidazolium salts, were studied. The reported results can be considered as a continuation of long-term studies focused on the synthesis and applications of 2-unsubstituted imidazole N-oxides.
Keywords: imidazole N-oxides; mechanochemistry; imidazolium salts; NHC carbenes; sulfur-transfer reactions; imidazole-2-thiones

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:imidazole N-oxides; mechanochemistry; imidazolium salts; NHC carbenes; sulfur- transfer reactions; imidazole-2-thiones
Language:English
Date:28 May 2022
Deposited On:30 May 2022 06:23
Last Modified:26 Feb 2024 02:53
Publisher:MDPI Publishing
ISSN:2073-4344
OA Status:Gold
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.3390/catal12060589
Project Information:
  • : FunderNational Science Centre (Cracow, Poland)
  • : Grant ID2016/23/G/ST5/04115/1
  • : Project Title
  • Content: Published Version
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)