Diversity-oriented synthesis of imidazo[1,2- a][1,3,5]triazine derivatives from 2-amine-[1,3,5]triazines with ketones

Wanqiu Zhao; Cheng Zhang; Pengzhen Zhong; Wei Zhou; Chen Zhang; Dong-Mei Cui

doi:10.1039/d1cc04294g

Diversity-oriented synthesis of imidazo[1,2- a][1,3,5]triazine derivatives from 2-amine-[1,3,5]triazines with ketones

Chem Commun (Camb). 2021 Oct 14;57(82):10715-10718. doi: 10.1039/d1cc04294g.

Authors

Wanqiu Zhao¹, Cheng Zhang¹, Pengzhen Zhong¹, Wei Zhou¹, Chen Zhang², Dong-Mei Cui¹

Affiliations

¹ College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, China. cuidongmei@zjut.edu.cn.
² School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.

PMID: 34581713
DOI: 10.1039/d1cc04294g

Abstract

An I₂-mediated annulation of 2-amino[1,3,5]triazines and ketones for the synthesis of imidazo[1,2-a][1,3,5]triazines is presented. Electron rich, or electron poor acetophenone and heterocycle ketones, as well as propiophenone, are functionalized with 2-amino-[1,3,5]triazines. Another class of imidazo[1,2-a][1,3,5]triazines tethered with an additional 1,2-dicarbonyl motif through the combination of annulation and C-H functionalization were obtained instead by changing the reaction conditions. The new methods are practically straightforward and applicable on a gram scale.