Triflic anhydride mediated cyclization of 5-hydroxy-substituted pyrrolidinones for the preparation of α-trifluoromethylsulfonamido furans

A Padwa, P Rashatasakhon…

Index: Padwa, Albert; Rashatasakhon, Paitoon; Rose, Mickea Journal of Organic Chemistry, 2003 , vol. 68, # 13 p. 5139 - 5146

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Citation Number: 28

Abstract

The reaction of α-angelica lactone with alkylamines under aqueous conditions afforded 5- hydroxy-5-methylpyrrolidinones in high yield. When the reaction was carried out under anhydrous conditions, the only products obtained were the corresponding 4-oxopentanoic acid amides. Treatment of either class of compound with triflic anhydride (Tf2O) in pyridine resulted in the formation of various substituted sulfonamidofurans. The suggested ...