Facilitation of addition-elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol.
SNAr displacement reactions of 6-cyclohexylmethoxy-2-fluoropurine, 6-amino-2-butylsulfonyl-4-cyclohexylmethoxypyrimidine and 2-amino-6-chloropurine with substituted anilines (e.g. the weakly nucleophilic 4-aminobenzenesulfonamide) are dramaticallyaccelerated in the presence of trifluoroacetic acid and occur especially efficiently in 2,2,2-trifluoroethanol solvent.
Whitfield
Hayley J
HJ
School of Natural Sciences--Chemistry, University of Newcastle upon Tyne, Bedson Building, Newcastle upon Tyne, UK NE1 7RU.
Griffin
Roger J
RJ
Hardcastle
Ian R
IR
Henderson
Andrew
A
Meneyrol
Jerome
J
Mesguiche
Veronique
V
Sayle
Kerry L
KL
Golding
Bernard T
BT
D015394:Molecular Structure; D011687:Purines / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D014269:Trifluoroacetic Acid / Q000737:chemistry*; D014270:Trifluoroethanol / Q000737:chemistry*
D011687:Purines; D011743:Pyrimidines; D012997:Solvents; D014270:Trifluoroethanol; D014269:Trifluoroacetic Acid