Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones

• Viktor M. Tkachuk,
• Oleh O. Lukianov,
• Mykhailo V. Vovk,
• Isabelle Gillaizeau and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191

• access to other C5-substituted and C5-unsubstituted pyrimidin-2(1H)-ones is beyond the synthetic scope of this approach. At the same time, simple N1-unsubstituted pyrimidin-2(1H)-ones 1 (see Figure 1b) are readily available on a multigram scale from inexpensive reagents [32][33][34] and can serve as

• required for the coupling are not tolerated with the highly electrophilic ketimine moiety of 4-trifluoromethylpyrimidin-2(1H)-ones. The CEL reaction was successfully applied in the N-arylation of many heterocyclic systems [35][36][37] including non-fluorinated pyrimidin-2(1H)-ones [38][39] under mild

• pyrimidin-2(1H)-ones 5a–e exhibit fluorescence properties with emission of λmax = 490–532 nm in CH2Cl2 solution. In order to analyze the effect exerted on the Chan–Evans–Lam arylation by 4-, 5-, and 6-substituents on the pyrimidine ring and also aiming at the further functionalization of pyrimidin-2(1H)-one

Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones

• Sergii V. Melnykov,
• Andrii S. Pataman,
• Yurii V. Dmytriv,
• Svitlana V. Shishkina,
• Mykhailo V. Vovk and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2017, 13, 2617–2625, doi:10.3762/bjoc.13.259

• synthesis of novel isomeric 4(6)-trifluoromethylated 1,2,3,4-tetrahydro- and perhydro-(2-oxopyrimidin-4-yl)acetic acid derivatives. Keywords: ketimines; malonic acid; Michael- and Mannich-type decarboxylative addition; pyrimidin-2(1H)-ones; regioselectivity; trifluoromethyl group; Introduction

• regioisomeric Mannich-type 1,2-adducts are more likely to be formed. These observations allowed us to develop selective methods for the synthesis of functionalized partially saturated 4-trifluoromethyl-substituted pyrimidin-2(1H)-ones, in particular, 4,5-dihydroorotic acid analogues 3 [39]. Here we report the