期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2015, 期 5, 页码 1020-1027出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403169
关键词
Cyclization; Regioselectivity; Nitrogen heterocycles; Chalcogens; Reaction mechanisms; Density functional calculations
资金
- Ministerio de Economia y Competitividad (MINECO), Gobierno de Espana
- European Union (EU) (Fondos Europeos para el Desarrollo Regional (FEDER) [CTQ2009-13083, CTQ2013-47494-P]
- Generalitat Valenciana [ACOMP2012-212, ISIC2012/001]
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-toexcellent 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.
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