C-H Methylation of Iminoamido Heterocycles with Sulfur Ylides.

C-H Methylation of Iminoamido Heterocycles with Sulfur Ylides. Angew Chem Int Ed Engl. 2020 Sep 15;: Authors: Ghosh P, Kwon NY, Kim S, Han S, Lee SH, An W, Mishra NK, Han SB, Kim IS Abstract The direct methylation of N -heterocycles is an important transformation for the advancement of pharmaceuticals, agrochemicals, functional materials, and other chemical entities. Herein, the unprecedented C(sp 2 )-H methylation of iminoamido heterocycles as nucleoside base analogues is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional group tolerance were attained. Moreover, this method can be readily applied to the site-selective methylation of azauracil nucleosides. The feasibility of gram-scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium-labeling experiments aided the elucidation of a plausible reaction mechanism. PMID: 32930471 [PubMed - as supplied by publisher]
Source: Angewandte Chemie - Category: Chemistry Authors: Tags: Angew Chem Int Ed Engl Source Type: research