Direct Access to 2-Thioxooxazolidin-4-ones and Oxazolidine-2,4-diones from [alpha]-Keto Thioesters through Thiolate Transfer

We report a direct synthesis of 2-thioxooxazolidin-4-ones and oxazolidine-2,4-diones from [alpha]-keto thioesters with sodium thiocyanate or potassium cyanate, respectively. The reactions proceed through nucleophilic substitution of a thioester with thiocyanate/cyanate anion, thiolate anion addition...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-12, Vol.359 (24), p.4405
Main Authors: Maity, Rajib, Naskar, Sandip, Mal, Kanchan, Biswas, Sandipa, Das, Indrajit
Format: Article
Language:English
Subjects:
Anions
Carbonyls
Oxazolidine
Sodium thiocyanate
Thioesters
Online Access:Get full text
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Summary:We report a direct synthesis of 2-thioxooxazolidin-4-ones and oxazolidine-2,4-diones from [alpha]-keto thioesters with sodium thiocyanate or potassium cyanate, respectively. The reactions proceed through nucleophilic substitution of a thioester with thiocyanate/cyanate anion, thiolate anion addition to carbonyl carbon, and subsequent intramolecular C-O heterocyclization.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701020