Multicomponent Synthesis of Imidazo[1,2- a]pyridines: Aerobic Oxidative Formation of C-N and C-S Bonds by Flavin-Iodine-Coupled Organocatalysis

Hayaki Okai; Kazumasa Tanimoto; Ryoma Ohkado; Hiroki Iida

doi:10.1021/acs.orglett.0c02929

Multicomponent Synthesis of Imidazo[1,2- a]pyridines: Aerobic Oxidative Formation of C-N and C-S Bonds by Flavin-Iodine-Coupled Organocatalysis

Org Lett. 2020 Oct 16;22(20):8002-8006. doi: 10.1021/acs.orglett.0c02929. Epub 2020 Oct 2.

Authors

Hayaki Okai¹, Kazumasa Tanimoto¹, Ryoma Ohkado¹, Hiroki Iida¹

Affiliation

¹ Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan.

PMID: 33006477
DOI: 10.1021/acs.orglett.0c02929

Abstract

Herein, we report an aerobic oxidative C-N bond-forming process that enables the facile synthesis of imidazo[1,2-a]pyridines and takes advantage of a coupled organocatalytic system that uses flavin and iodine. Furthermore, the dual catalytic system can be applied to the one-pot, three-step synthesis of 3-thioimidazo[1,2-a]pyridines from aminopyridines, ketones, and thiols.

Publication types

Research Support, Non-U.S. Gov't