Expedient Base-Mediated Desulfitative Dimethylamination, Oxidation, or Etherification of 2-(Methylsulfanyl)-3,5-dihydro-4H-imidazol-4-one Scaffolds

Shahnawaz Khan; Vikas Tyagi; Rohit Mahar; Vikas Bajpai; Brijesh Kumar; Prem M. S. Chauhan

doi:10.1055/s-0033-1338499

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(17): 2405-2412
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

Shahnawaz Khan

^aMedicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, 226 001, India eMail: premsc58@hotmail.com eMail: prem_chauhan_2000@yahoo.com Fax: +91(522)2623405

,

Vikas Tyagi

^aMedicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, 226 001, India eMail: premsc58@hotmail.com eMail: prem_chauhan_2000@yahoo.com Fax: +91(522)2623405

,

Rohit Mahar

^bSophisticated Analytical Instrument Facility, CSIR-Central Drug Research Institute, Lucknow, 226 001, India

,

Vikas Bajpai

^bSophisticated Analytical Instrument Facility, CSIR-Central Drug Research Institute, Lucknow, 226 001, India

,

Brijesh Kumar

^bSophisticated Analytical Instrument Facility, CSIR-Central Drug Research Institute, Lucknow, 226 001, India

,

Prem M. S. Chauhan*

^aMedicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, 226 001, India eMail: premsc58@hotmail.com eMail: prem_chauhan_2000@yahoo.com Fax: +91(522)2623405

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Abstract

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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.

Key words

heterocycles - aminations - etherifications - oxidations - ketones - amines - ethers

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Referenzen

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