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- W1576978836 abstract "Abstract A very efficient synthesis of 5‐chalcogenyl‐1,3‐oxazin‐2‐ones has been accomplished by the chalcogen‐mediated yne–carbamate cyclisation of chiral, non‐racemic N ‐Cbz‐protected propargylic amines using PhXY (X = Se, S, Te; Y = Br or Cl) as electrophile sources. The reactions gave good‐to‐excellent yields for a wide range of substrates. In all cases the reaction was totally regioselective, occurring by a 6‐ endo ‐ dig process regardless of the nature of the reagent and of the substituents in the starting material. This methodology permits the formation of the 1,3‐oxazin‐2‐one moiety as well as the simultaneous installation of a chalcogen functionality onto the heterocyclic ring. The experimental results have been rationalised by theoretical studies at the B3LYP/6‐311G* level of theory." @default.
- W1576978836 created "2016-06-24" @default.
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- W1576978836 date "2014-12-23" @default.
- W1576978836 modified "2023-10-15" @default.
- W1576978836 title "Efficient Synthesis of 5-Chalcogenyl-1,3-oxazin-2-ones by Chalcogen-Mediated Yne-Carbamate Cyclisation: An Experimental and Theoretical Study" @default.
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- W1576978836 doi "https://doi.org/10.1002/ejoc.201403169" @default.
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