C-H Methylation of Iminoamido Heterocycles with Sulfur Ylides**
- Authors
- Ghosh, P[Ghosh, Prithwish]; Kwon, NY[Kwon, Na Yeon]; Kim, S[Kim, Saegun]; Han, S[Han, Sangil]; Lee, SH[Lee, Suk Hun]; An, W[An, Won]; Mishra, NK[Mishra, Neeraj Kumar]; Han, SB[Han, Soo Bong]; Kim, IS[Kim, In Su]
- Issue Date
- Jan-2021
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- alkylation; C& #8722; H functionalization; methylation; N-heterocycles; sulfur ylides
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.60, no.1, pp.191 - 196
- Indexed
- SCIE
SCOPUS
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Volume
- 60
- Number
- 1
- Start Page
- 191
- End Page
- 196
- URI
- https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/2325
- DOI
- 10.1002/anie.202010958
- ISSN
- 1433-7851
- 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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