Synthesis of 5-fluorovinyl derivatives of pyrimidines via Suzuki–Miyaura coupling and their 1,3-dipolar cycloaddition reactions with nitrones

Kinetic aspects of [3+2] cycloaddition reactions between (E)-3,3,3-trichloro-1-nitroprop-1-ene and ketonitrones

“…The mechanistic aspects of [3?2] cycloaddition reactions have recently drawn ever greater attention from organic chemists [1][2][3][4][5][6][7][8][9][10]. It turned out that in the case of reactions including strongly electrophilic dipolarophiles, a stepwise, zwitterionic mechanism may compete with a classical one-step mechanism.…”

“…In recent years, it has been proven that such a mechanism takes place e.g. in the case of [3?2] cycloadditions between N-methylnitrone and fluorinated alkenes [6] as well as between azomethine ylides and dialkyl-2,3-dicyanobut-2-enedioates [10]. The stepwise, zwitterionic mechanism of [3?2] cycloaddition may also be enforced by the presence of ionic liquids in the reaction medium [3].…”

The nitrogen inversion in fused isoxazolidinyl derivatives of substituted uracil: synthesis, NMR and computational analysis

“…In the course of our work on fluorovinyl derivatives of nucleic acid bases and their cycloaddition reactions with nitrones [32][33][34], we decided to synthesize a series of isoxazolidinyl derivatives of 5-fluorouracil in 1,3-dipolar cycloaddition of N-fluorovinyl-5-fluorouracil with nitrones. Unexpectedly, we obtained exclusively, without any competitive reaction, the cycloaddition product not to exocyclic, but to endocyclic double bond with the formation of fused ring.…”

Synthesis and applications of fluorinated nucleoside analogues

“…Wó jtowicz-Rajchel and Koroniak described very recently the synthesis of 5-fluoroalkenyl derivatives of pyrimidines via Suzuki-Miyaura coupling reactions [132].…”

“…Wó jtowicz and Koroniak described in 2012 a simple two-step synthesis of a new class of fluorinated isoxazolidinyl derivatives of pyrimidine [132]. The reactions proceed via the Suzuki-Miyaura coupling followed by highly regioselective 1,3-dipolar cycloaddition with nitrones.…”