Publication: Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3-oxides
Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3-oxides
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Mlostoń, G., Celeda, M., Prakash, G. K. S., Olah, G. A., & Heimgartner, H. (2000). Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3-oxides. Helvetica Chimica Acta, 83, 728–738. https://doi.org/10.1002/(SICI)1522-2675(20000412)83:4<728::AID-HLCA728>3.0.CO;2-B
Abstract
Abstract
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 -
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- Mlostoń, Grzegorz
- Celeda, Malgorzata
- Prakash, G K Surya
- Olah, George A
- Heimgartner, Heinz
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Mlostoń, G., Celeda, M., Prakash, G. K. S., Olah, G. A., & Heimgartner, H. (2000). Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3-oxides. Helvetica Chimica Acta, 83, 728–738. https://doi.org/10.1002/(SICI)1522-2675(20000412)83:4<728::AID-HLCA728>3.0.CO;2-B
