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- W2786799894 abstract "Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C–C and C–S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of the thioester group. The reactions are proposed to proceed through Curtius rearrangement of the initially formed α-keto acyl azide to generate an acyl isocyanate intermediate, which reacts further with an additional amount of azide or water and rearranges to afford the corresponding products. To demonstrate the potentiality of the method, one-step syntheses of pivaloylurea and isovaleroylurea, displaying anticonvulsant activities, have been carried out." @default.
- W2786799894 created "2018-02-23" @default.
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- W2786799894 date "2018-02-08" @default.
- W2786799894 modified "2023-10-17" @default.
- W2786799894 title "Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C–C and C–S Bond Cleavages: Synthesis of <i>N</i>-Acylureas and Amides" @default.
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- W2786799894 doi "https://doi.org/10.1021/acs.joc.7b03054" @default.
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