Selective introduction of a fluorine atom into a bioactive molecule often yields compounds with useful and specific properties. We have studied the fluorination of some pharmacologically active compounds by using the N-fluoro[(bistrifluoromethyl)sulfonyl]-imide 1 as the source of “positive fluorine”. 3-[1-Phenyl-3-oxobutyl]-2H-benzopyran-2,4- dione (warfarin) was cleanly fluorinated by treatment with the N-fluoroimide 1 and the corresponding 3-fluorowarfarin 2 (RC6H5) was formed. Similarly, sulfinpyrazone and several barbituricacidderivatives afforded corresponding fluorination products 3 (RC6H5SO) and 4 (R1, R2=H, alk., ar., …). Various other fluorinated analogues of pharmacologically active compounds (e.g. 2, Rp-Cl-C6H4; 3, RC2H5) have also been synthetized. Desired products have invariably been isolated in high yields. The different reactivities of the various functional groups present in the employed substrate provided interesting information on selectivity and functional group compatibility of electrophilicfluorination reactions with the N-fluoroimide 1.
Electrophilic fluorination of warfarin, sulfinpyrazone and barbituric acid derivatives
RESNATI, GIUSEPPE
1992-01-01
Abstract
Selective introduction of a fluorine atom into a bioactive molecule often yields compounds with useful and specific properties. We have studied the fluorination of some pharmacologically active compounds by using the N-fluoro[(bistrifluoromethyl)sulfonyl]-imide 1 as the source of “positive fluorine”. 3-[1-Phenyl-3-oxobutyl]-2H-benzopyran-2,4- dione (warfarin) was cleanly fluorinated by treatment with the N-fluoroimide 1 and the corresponding 3-fluorowarfarin 2 (RC6H5) was formed. Similarly, sulfinpyrazone and several barbituricacidderivatives afforded corresponding fluorination products 3 (RC6H5SO) and 4 (R1, R2=H, alk., ar., …). Various other fluorinated analogues of pharmacologically active compounds (e.g. 2, Rp-Cl-C6H4; 3, RC2H5) have also been synthetized. Desired products have invariably been isolated in high yields. The different reactivities of the various functional groups present in the employed substrate provided interesting information on selectivity and functional group compatibility of electrophilicfluorination reactions with the N-fluoroimide 1.File | Dimensione | Formato | |
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