한빛사 논문
성균관대학교
Prithwish Ghosh,[a,†] Na Yeon Kwon,[a,†] Saegun Kim,[a] Sangil Han,[a] Suk Hun Lee,[a] Won An,[a] Neeraj Kumar Mishra,[a] Soo Bong Han,[b,c] and In Su Kim*[a]
[a] School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea
[b] Division of Bio & Drug Discovery, Korea Research Institute of Chemical Technology, Daejeon 34114, Republic of Korea
[c] Department of Medicinal and Pharmaceutical Chemistry, University of Science and Technology, Daejeon 34113, Republic of Korea
*Corresponding author
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.
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TOP52020년 후보
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