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Synthesis 2013; 45(17): 2405-2412
DOI: 10.1055/s-0033-1338499
DOI: 10.1055/s-0033-1338499
paper
Expedient Base-Mediated Desulfitative Dimethylamination, Oxidation, or Etherification of 2-(Methylsulfanyl)-3,5-dihydro-4H-imidazol-4-one Scaffolds
Further Information
Publication History
Received: 30 January 2013
Accepted after revision: 03 June 2013
Publication Date:
11 July 2013 (online)
Abstract
The dimethylamino functionality is generally introduced onto the 3,5-dihydro-4H-imidazol-4-one skeleton by treatment of a halogenated derivative with low-boiling dimethylamine at a high temperature and pressure. The corresponding aliphatic ethers are usually prepared by Williamson ether synthesis, but the available transition-metal-catalyzed methods require highly toxic reagents (such as dimethyl sulfate or methyl halides) and expensive metal catalysts, and they entail harsh reaction conditions and complex workups. A simple and efficient method is described for base-mediated desulfitative dimethylamination, oxidation, or etherification at the C2-position of the 2-(methylsulfanyl)-3,5-dihydro-4H-imidazol-4-one scaffold by using potassium carbonate and aqueous N,N-dimethylformamide or an aliphatic alcohol.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are copies of 1H and 13C NMR spectra of all the compounds.
- Supporting Information
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