Catalytic C–H bond functionalisation of purine and pyrimidine nucleosides: a synthetic and mechanistic perspective

Abstract

C-H bond functionalisation of heteroarenes, especially nucleosides, has received a lot of attention in the past few years. This review describes the state-of the art in this area with a global aspiration for possibly functionalising purine and pyrimidine moieties in more complex biomolecular systems, such as DNA/RNA in the near future.'

Thermal Decomposition of Sulfur Compounds and their Role in Coke Formation during Steam Cracking of Heptane

“…The developed strategy was successfully extended to prepare an arylated pyrimidine base by using the 5‐phenyluracil iodonium salt ( 1q ), which afforded 5‐phenyluracil ( 2q ) in 50 % yield. Arylated uracils are well known for their interesting medicinal properties 16…”

Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

“…It showed that the content of Ru in the solution phase was negligible (2.1 ppb). While from these results, it may be possible that the actual catalyst for the reactions under the standard conditions was the leached homogeneous species of Ru, such as clusters [53][54][55][56][57][58][61][62][63][64][65], the ICP-MS results taken in conjunction with the results of the Hg poisoning test and, more importantly, the three-phase test, could allow us to reach the conclusion that the reactions were catalysed by a heterogeneous process.…”

Concise Xanthine Synthesis through a Double‐Amidination Reaction of a 6‐Chlorouracil with Amidines using Base‐Metal Catalysis

“…S N AE of the C6h alogen by an amidine leads to an N-uracil amidine (B), which can be further converted to the corresponding xanthine (C)b yad irect oxidative amidination reaction. [7] The required amidine reagents can be easily prepared using aP innera pproach, starting from the corresponding nitriles and amines,a nd allow regioselective installation of R 7 at N7. [8,9] In comparison to the Traube synthesis, our approach is shorter,p revents ap ost-functionalization step An ew and concise route towards xanthines through ad oubleamidination reactioni sd escribed;c onsecutive intermolecular CÀCl and intramolecular oxidative CÀHa midination.…”

“…Herein we report a new and general approach towards N 1‐, N 3‐, N 7‐, and C 8‐substituted xanthines, involving two consecutive C−N bond‐forming steps starting from readily available N 1, N 3‐substituted 6‐chlorouracils ( A , Scheme ). S N AE of the C 6 halogen by an amidine leads to an N ‐uracil amidine ( B ), which can be further converted to the corresponding xanthine ( C ) by a direct oxidative amidination reaction . The required amidine reagents can be easily prepared using a Pinner approach, starting from the corresponding nitriles and amines, and allow regioselective installation of R 7 at N 7 .…”