Transition Metal Free Intermolecular Direct Oxidative C–N Bond Formation to Polysubstituted Pyrimidines Using Molecular Oxygen as the Sole Oxidant

Abstract

Various polysubstituted pyrimidines are smoothly formed via a base-promoted intermolecular oxidation C-N bond formation of allylic C(sp(3))-H and vinylic C(sp(2))-H of allyllic compounds with amidines using O2 as the sole oxidant. This protocol features protecting group free nitrogen sources, good functional group tolerance, high atom economy, and environmental advantages.

Research developments in the syntheses, anti-inflammatory activities and structure–activity relationships of pyrimidines

“…SAR analysis veried that the introduction of two aryl moieties on the adjacent positions 2 and 3 in imidazo [1,2-a]pyrimidine analogs selectively improved the inhibitory effects of the target derivatives against COX-2 activity. 86 Singour and coworkers reported the synthesis of ve 2chloropyrimidine derivatives (50)(51)(52)(53)(54) by the reaction of 2,4,6 trichloropyrimidine either with aromatic amines or amides (Scheme 23). The synthesized 2-chloropyrimidines were subsequently investigated for their COX-2 inhibitory activities.…”

Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes

“…The allyl group is an important structural unit for latefunctional group transformations. [126] The introduction of allyl moieties into organic compounds is significant. Photocatalyzed α-allylic alkylations of tertiary amines have attracted continuous attention, compared with the traditional cross-dehydrogenative coupling (CDC) strategies.…”

Recent Approaches to the Synthesis of Pyrimidine Derivatives

“…Wu and Jiang very recently described the condensation of amidines with allylarene compounds 16 under basic conditions in the presence of oxygen (Scheme ) . The reaction mechanism is different from those of the reactions described above, because it is unlikely that an enone or a related intermediate is formed in the process.…”