Synthesis of 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones via an unexpected microwave-assisted cascade reaction

An unprecedented route for the synthesis of N-1 substituted 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones is disclosed starting from 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones. The method comprises treatment of various 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones with Na2CO3 in water under microwave irradiation providing the respective 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones in good yields, via hydrolysis of the thioether bond and subsequent nucleophilic displacement of the chlorine by the in situ generated thiophenol. The obtained compounds are excellent precursors for the diversity oriented synthesis of pharmacologically active α,β-dicarbonyl compounds.

Graphical abstractAn unprecedented route for the synthesis of N-1 substituted 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones is disclosed starting from 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones. The method comprises treatment of various 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones with Na2CO3 in water under microwave irradiation providing the respective 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones in good yields, via hydrolysis of the thioether bond and subsequent nucleophilic displacement of the chlorine by the in situ generated thiophenol. The obtained compounds are excellent precursors for the diversity oriented synthesis of pharmacologically active α,β-dicarbonyl compounds.Figure optionsDownload full-size imageDownload as PowerPoint slide