The use of sulfur ylides in the synthesis of 3-alkyl(aryl)thio-4- trifluoromethylpyrroles from mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates
In this report, we describe a new method for the synthesis of densely functionalized pyrroles. Reaction of mesoionic 1,3-oxazolium-5-olates with various S-ylides proceeds via nucleophilic addition followed by opening of the oxazole ring and subsequent cyclization to multisubstituted pyrroles bearing both a trifluoromethyl and alkyl(aryl)thio group at 3- and 4-positions.
Saijo, Ryosuke,Kawase, Masami
scheme or table
p. 2782 - 2785
(2012/07/17)
New synthesis of 3-trifluoromethylpyrroles by condensation of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates with phosphorus ylides
Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines with trifluoroacetic anhydride, react with phosphorus ylides to give β-trifluoromethylpyrroles (2) in good yields. The novel ring transformations
Saijo, Ryosuke,Hagimoto, Yuri,Kawase, Masami
supporting information; experimental part
p. 4776 - 4779
(2011/01/03)
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