5-Membered N-heterocyclic compounds by dimethyl carbonate chemistry

A stable four-membered N-heterocyclic carbene.

The synthesis of the first four-membered N-heterocyclic carbene is described. Depending on the substituents on the nitrogen atoms, it is possible to characterize at room temperature the carbene dimer or the free carbene. Crystallographic analyses are provided for these carbene species.

New developments in dimethyl carbonate chemistry*

Dimethylcarbonate (DMC) is a valuable methylating reagent which can replace methyl halides and dimethylsulfate in the methylation of a variety of nucleophiles. It couples tunable reactivity and unprecedented selectivity toward mono-Cand mono-N-methylation in the reactions of acidic CH2 and primary aromatic amines, respectively. In addition, it is a prototype example of a green reagent, since it...

Construction of Five-Membered Heterocyclic Compounds via Radical Cyclization

Introduction of Medicinal Chemistry & Heterocyclic Compounds

Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate.

The reaction of 1,4-diols with dimethyl carbonate in the presence of a base led to selective and high-yielding syntheses of related five-membered cyclic ethers. This synthetic pathway has the potential for a wide range of applications. Distinctive cyclic ethers and industrially relevant compounds were synthesized in quantitative yield. The reaction mechanism for the cyclization was investigated...