Azidomethylation of Nucleobases and Related N-Heterocycles, Benzazoles, and Bis(arene)sulfonimides Using Azidomethyl Esters with Silyl Triflates

Ryoga Sawahata; Yuga Takagi; Yoshiaki Kitamura

doi:10.1021/acs.orglett.4c00938

Azidomethylation of Nucleobases and Related N-Heterocycles, Benzazoles, and Bis(arene)sulfonimides Using Azidomethyl Esters with Silyl Triflates

Org Lett. 2024 May 10;26(18):3806-3809. doi: 10.1021/acs.orglett.4c00938. Epub 2024 Apr 25.

Authors

Ryoga Sawahata¹, Yuga Takagi², Yoshiaki Kitamura^{1

2

3

4}

Affiliations

¹ Department of Life Science and Chemistry, Graduate School of Natural Science and Technology, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
² Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
³ United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
⁴ Center for One Medicine Innovative Translational Research (COMIT), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.

PMID: 38662603
DOI: 10.1021/acs.orglett.4c00938

Abstract

An efficient method for the azidomethylation of amines using azidomethyl esters with silyl triflates is described. This protocol enables the azidomethylation of various amines that can be activated with silyl groups, including nucleobases.