Recent Advances in Direct C–H Functionalization of Pyrimidines

Abstract

Data spanning the period 2000–2017 on the direct C–H functionalization of pyrimidines are collected and discussed in this review. This demonstrates the surge of interest and creativity that this field of chemistry has experienced during the last two decades. Plausible applications of highly functionalized pyrimidines are also discussed.1 Introduction2 Transition-Metal-Catalyzed C–H Functionalization of Pyrimidine Derivatives3 Transition-Metal-Free Direct C–H Functionalization of Pyrimidine Derivatives4 Deprotonative Metalation of Pyrimidine Derivatives5 Conclusions

Synthesis, photophysical and redox properties of the 2,5,7-tri(het)aryl-[1,2,4]triazolo[1,5-a]pyrimidines

“…One of the main routes to substituted pyrimidines is the direct C-H functionalization, 1,14 otherwise known as nucleophilic aromatic substitution of hydrogen (SN H ). 15,16 This approach can also be applied to the TAPsystem, as already demonstrated by Jie Wu and colleagues who synthesized 2,7-diaryl-substituted TAPs using direct copper-catalyzed CH functionalization.…”

An Efficient Access to Pyrimidine‐based Polyfunctional Heterocycles with Anticipated Antibacterial Activity

“…Interestingly, pyrimidines are not only revealing a profound antitumor activity but also acting as unique HIV reverse transcriptase inhibitors . Moreover, many pyrimidine derivatives are considered to be antibiotics, anticonvulsant, and calcium channel blockers . Clearly, pyrimidines owe their therapeutic applications to the fact that pyrimidine base is existing in uracil, thymine, and cytosine, which are crucial building units of the two essential nucleic acids, deoxyribonucleic acid, and ribonucleic acid.…”

Palladium-Catalyzed C–H Heteroarylation of 2,5-Disubstituted Imidazoles

“…Direct functionalization of unactivated C-H bonds of organic molecules requires no preactivation steps, and can thus facilitate the synthesis and structural optimization of functional organic compounds, including drugs, starting from readily available starting materials. [1][2][3][4][5][6][7][8][9][10] In our studies toward the development of small-molecule aggregation inhibitors of amyloid β peptides (Aβ) as potential drugs to treat Alzheimer's disease, 11) we became interested in the synthesis of biaryl compounds comprising a six-membered N-heterocycle and an imidazole ring. More generally, arylated imidazoles are a fundamental scaffold of various drug-lead molecules.…”