6533b7d0fe1ef96bd125a3be
RESEARCH PRODUCT
Synthesis of Densely Functionalised 5-Halogen-1,3-oxazin-2-ones byHalogen-Mediated Regioselective Cyclisation of N-Cbz-ProtectedPropargylic Amines: A Combined Experimental and Theoretical Study
Luis R. DomingoJosé R. PedroAlicia MonleonGonzalo BlayM. Carmen Muñozsubject
Propargylic aminesReaction mechanismChemistryReaction mechanismsOrganic ChemistryRegioselectivityGeneral ChemistryCatalysisOxazinonesDensity functional calculationsRegioselectivityHalocyclisationYield (chemistry)FISICA APLICADAHalogenElectrophileOrganic chemistrydescription
A very efficient synthesis of 5-halogen-1,3-oxazin-2-ones has been accomplished by the halocyclisation reaction of chiral nonracemic N-carbobenzyloxy (N-Cbz)-protected propargylic amines by using I-2, Br-2 and Cl-2 as electrophile sources. The nature of the halogen influences the reaction time and yield. However, in all cases the reaction is totally regioselective taking place through a 6-endo-dig process regardless of the nature of the halogen and of the substituents in the starting material. To rationalise the experimental results, theoretical studies at the B3LYP/6-311G* level have been performed.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-05-31 |