Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.
O-Ethyl S-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl xanthate was readily prepared on a large scale and shown to undergo very efficient intermolecular radical additions to unactivated alkenes. The products were further elaborated by exploiting both radical and ionic processes to provide a variety of trifluoromethyl-substituted derivatives, including medicinally relevant triazoles. In particular, the application of a radical allylation on the initial adducts leads to structures that are able to undergo intramolecular [4 + 2] cycloaddition reactions.
Laboratoire de SynthèseOrganique, UMR 7652 CNRS/EcolePolytechnique Palaiseau 91128 Cedex, France.
Ling
L
Qin
Laboratoire de SynthèseOrganique, UMR 7652 CNRS/EcolePolytechnique Palaiseau 91128 Cedex, France.
Samir Z
SZ
Zard
D000475:Alkenes / Q000737:chemistry*; D061565:Cycloaddition Reaction; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
D000475:Alkenes; D005663:Furans; C000600272:O-ethyl S-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)methyl xanthate; D010069:Oxadiazoles; D014230:Triazoles; C583463:1,3,4-oxadiazole; C045575:1,2,4-triazole