The reaction of cyclic carbinol amides with triflic anhydride as a method to prepare alpha-trifluoromethyl-sulfonamido furans.
[reaction: see text] A novel synthesis of alpha-trifluoromethyl-sulfonamido furans via the reaction of cyclic carbinol amides with triflic anhydride has been developed. The reaction proceeds under very mild conditions with a wide set of representative lactams to provide the alpha-trifluoromethyl-sulfonamido-substituted furan in high yield. Rapid access to a 5-substituted indoline can be achieved by thermolysis of the N-but-3-enyl-substituted sulfonamido furan.
Rashatasakhon
Paitoon
P
Department of Chemistry, Emory University, Atlanta, Georgia 30322,USA.
Padwa
Albert
A
D000577:Amides / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis; D007769:Lactams / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry
D000577:Amides; D005663:Furans; D006571:Heterocyclic Compounds; D007211:Indoles; D007769:Lactams; D008698:Mesylates; D013449:Sulfonamides; C057812:indoline; C474725:triflic anhydride