Synthesis of some 5-perfluoroalkenyl derivatives of uracil

Synthesis and applications of fluorinated nucleoside analogues

“…Particularly the palladium catalyzed cross couplings of thermally stable perfluoroalkenyl zinc reagents with aryl iodides in Negishi reactions are very convenient and useful tool in the synthesis of arylperfluoroalkenes. Koroniak and coworkers used a general procedure for palladium(0) catalysed coupling of organometallic, unsaturated fragments with aromatic species, to develop a convenient method for the preparation of 5-perfluoroalkenylsubstituted uracils [130,131]. 1,3-Dimethyl-5-iodouracil and 1,3-dimethyl-5-bromo-6-azauracil reacted smoothly with perfluoroalkenylzinc iodides in the presence of Pd(PPh 3 ) 4 catalyst resulting in the formation of the derivatives 331 as potential synthons of appropriate nucleoside analogues (Scheme 64).…”

Photoisomerization of fluorinated 1,3-dimethyl-5-propenyl uracils as a cycle of sequential reactions: Electrocyclization in its use in light-fueled nanomotors

“…The electronic donating/ accepting properties of substituents at the terminal position of a diene or cyclobutene could determine mode of motion and a stereospecificity of this reaction. Recently, we have studied extensively synthetic methodology to access 5-fluorinated alkenyl uracils as well as to determine their structural properties [13][14][15][16][17]. We have reported photochemical isomerization of 1,3-dimethyl-5-(1,2,3,3,3-pentafluoropropenyl)uracil [15] showing that torquoselectivity might be an important factor for understanding the mechanism of this transformation.…”

Palladium-catalysed cross coupling of perfluoroalkenyl zinc reagents with 5-halo-6-azauracils

“…[3][4][5] We reported a synthesis of some perfluoroalkenyl derivatives of uracil as potential synthons of appropriate nucleosides. 6 Our continuing interest in fluorinated analogues of nucleic acid bases prompted us to explore the possibility of using an 6-aza analogue of uracil. Numerous examples of reactions show that uracil and 6-azauracil derivatives behave in a similar way, but sometimes the seemingly simple reactions of 6-azauracil derivatives can make their chemistry fascinating.…”