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Silver(I)-catalysed carboxylative cyclisation of primary propargylic amines in neat water using potassium bicarbonate as a carboxyl source: an environment-friendly synthesis of Z-5-alkylidene-1,3-oxazolidin-2-ones

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Abstract

Herein, we report a mild and environment-friendly synthesis of Z-5-alkylidene-2-oxazolidinones in neat water, using a low loading (2 mol%) of silver carbonate as a catalyst. Instead of pressurised gaseous carbon dioxide, potassium bicarbonate was used as the source of carboxyl. An interesting solvent effect and a C–N cleavage side reaction with a 6-endo-dig mechanism are also discussed.

Graphical abstract: Silver(i)-catalysed carboxylative cyclisation of primary propargylic amines in neat water using potassium bicarbonate as a carboxyl source: an environment-friendly synthesis of Z-5-alkylidene-1,3-oxazolidin-2-ones

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Publication details

The article was received on 16 May 2019, accepted on 16 Jul 2019 and first published on 27 Jul 2019


Article type: Paper
DOI: 10.1039/C9GC01650C
Green Chem., 2019, Advance Article

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    Silver(I)-catalysed carboxylative cyclisation of primary propargylic amines in neat water using potassium bicarbonate as a carboxyl source: an environment-friendly synthesis of Z-5-alkylidene-1,3-oxazolidin-2-ones

    J. Qin, B. Wang and G. Lin, Green Chem., 2019, Advance Article , DOI: 10.1039/C9GC01650C

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