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- Title
2-(3-Bromophenyl)imidazo[2,1- b ]oxazole.
- Authors
Cores, Ángel; Villacampa, Mercedes; Menéndez, J. Carlos
- Abstract
The microwave-assisted reaction of 2-nitroimidazole with 3-bromophenacyl bromide in the presence of potassium carbonate as a base and dimethylformamide as a solvent afforded 2-(3-bromophenyl)imidazo[2,1-b]oxazole. The formation of this compound was explained via a domino mechanism comprising an initial N-alkylation reaction of the imidazole substrate, followed by the base-promoted deprotonation of the position adjacent to the carbonyl to give an enolate anion that finally cyclizes via an intramolecular SNAr reaction, with the loss of the nitro group as potassium nitrite. Then, the proposed 1-(3-bromophenacyl)-2-nitroimidazole intermediate could be isolated by reducing the reaction time and was shown to be a precursor of the imidazo[2,1-b]oxazole final product.
- Subjects
POTASSIUM carbonate; GROUP 15 elements; POTASSIUM bromide; PHTHALAZINE; PROTON transfer reactions; IMIDAZOLES; IMIDAZOPYRIDINES; NITRITES
- Publication
Molbank, 2023, Vol 2023, Issue 2, pM1616
- ISSN
1422-8599
- Publication type
Article
- DOI
10.3390/M1616