Quaternization of azido-N-heteroarenes with Meerwein reagent: A straightforward synthesis of 2-azido(benzo)imidazolium and related azido-N-heteroarenium tetrafluoroborates. (14th September 2022)

• Record Type: Journal Article
• Authors: Li, Yan; Wan, Ting-Biao; Guo, Bin; Qi, Xiao-Wen; Zhu, Chifan; Shen, Mei-Hua; Xu, Hua-Dong
• Is Part Of: Tetrahedron letters. Volume 106(2022)
• Publication Date: 2022-09-14
• Subjects: 2-Azido(benzo)imidazolium salt -- Organic azide -- Quaternization -- Meerwein reagent -- Diazotransfer reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154063
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 2-Azido(benzo)imidazolium salts have been made through quaternization of 2-Azido(benzo)imidazoles with Meerwein reagent at ambient conditions. This one-pot protocol is also applicable to 4 or 3-azidopyridines and appropriate azido(iso)quinolines to prepare correlative azido- N -heteroarenium salts. When compared with their precursors, improved diazotransfer reactivity was observed for several representative azido- N -heteroarenium salts in reaction with diethyl malonate.