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RESEARCH PRODUCT
Efficient Synthesis of 5-Chalcogenyl-1,3-oxazin-2-ones by Chalcogen-Mediated Yne-Carbamate Cyclisation: An Experimental and Theoretical Study
M. Carmen MuñozGonzalo BlayJosé R. PedroLuis R. DomingoAlicia Monleonsubject
Reaction mechanismCarbamateChemistrymedicine.medical_treatmentOrganic ChemistryRegioselectivityRing (chemistry)Medicinal chemistryChalcogenReagentElectrophilemedicineOrganic chemistryMoietyPhysical and Theoretical Chemistrydescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-12-23 | European Journal of Organic Chemistry |