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DOI: 10.1055/s-0036-1588984
Efficient Access to Original 6-Substituted 5-Nitro-2,3-dihydroimidazo[2,1-b]oxazoles
Publication History
Received: 25 January 2017
Accepted after revision: 08 March 2017
Publication Date:
04 April 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201712/lookinside/thumbnails/ss-2017-t0048-op_10-1055_s-0036-1588984-1.jpg)
Abstract
A one-pot sequential intramolecular cyclization and Suzuki–Miyaura or Sonogashira reaction under microwave irradiation are reported in the 5-nitro-2,3-dihydroimidazo[2,1-b]oxazole series. The intramolecular cyclization of 1-(2,4-dibromo-5-nitro-1H-imidazol-1-yl)propan-2-ol between the hydroxyethyl group and the bromine atom at the 2-position is carried out first, followed by optimization and generalization of the Suzuki–Miyaura and Sonogashira cross-coupling reactions of the bromine atom at the 4-position. The various boronic acids and alkynyl derivatives used to perform these palladium-catalyzed cross-coupling reactions allowed to substitute the 6-position of 5-nitro-2,3-dihydroimidazo[2,1-b]oxazole compounds.
Key words
5-nitroimidazole - Suzuki–Miyaura reaction - Sonogashira reaction - intramolecular cyclization - microwave - palladiumSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588984.
- Supporting Information
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