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Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3-oxides


Mloston, Grzegorz; Celeda, Malgorzata; Prakash, G K Surya; Olah, George A; Heimgartner, Heinz (2000). Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3-oxides. Helvetica Chimica Acta, 83:728-738.

Abstract

The reaction of 1,4,5-trisubstituted 1H-imidazole 3-oxides 1 with Ac2O in CH2Cl2 at 0 - 5° leads to the corresponding 1,3-dihydro-2H-imidazol-2-ones 4 in good yields. In refluxing Ac2O, the N-oxides 1 are transformed to N-acetylated 1,3-dihydro-2H-imidazol-2-ones 5. The proposed mechanisms for these reactions are analogous to those for N-oxides of 6-membered heterocycles (Scheme 2). A smooth synthesis of 1H-imidazole-2-carbonitriles 2 starting with 1 is achieved by treatment with trimethylsilanecarbonitrile (Me3SiCN) in CH2Cl2 at 0 - 5° (Scheme 3).

Abstract

The reaction of 1,4,5-trisubstituted 1H-imidazole 3-oxides 1 with Ac2O in CH2Cl2 at 0 - 5° leads to the corresponding 1,3-dihydro-2H-imidazol-2-ones 4 in good yields. In refluxing Ac2O, the N-oxides 1 are transformed to N-acetylated 1,3-dihydro-2H-imidazol-2-ones 5. The proposed mechanisms for these reactions are analogous to those for N-oxides of 6-membered heterocycles (Scheme 2). A smooth synthesis of 1H-imidazole-2-carbonitriles 2 starting with 1 is achieved by treatment with trimethylsilanecarbonitrile (Me3SiCN) in CH2Cl2 at 0 - 5° (Scheme 3).

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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
Language:English
Date:2000
Deposited On:29 Oct 2013 10:54
Last Modified:07 Dec 2017 23:12
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Loker Hydrocarbon Institute, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/(SICI)1522-2675(20000412)83:4<728::AID-HLCA728>3.0.CO;2-B

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