Copper-Catalyzed Coupling of Arylethynes and Aryltriazenes to Access Libraries of 1,2-Diketones and Their Efficacy in Synthesis of Triaryloxazoles, Imidazoles and Diaryl-Diazepines

Document Type

Article

Publication Date

5-20-2021

Abstract

Libraries of diaryl-1,2-diketones were synthesized by oxidative coupling of 1-aryl-ethynes with 1-aryl-triazenes, employing tetramethylguanidinium ionic liquid [TMG][CF3COO] and Cu(OAc)2. The synthesized compounds served as scaffolds for facile one-pot synthesis of diverse libraries of pharmaceutically important heterocycles in ionic liquid solvents. Thus BMIM-ionic liquid/CuI was utilized for the synthesis of triaryl-oxazoles, [TMG][HSO4]/NH4OAc was used to prepare triaryl-imidazoles, and [TMG][OAc] was employed for the synthesis of diaryl-diazepines. Reactions were performed in fresh as well as in recycled ionic liquids. The reported methods expand the available protocols for the synthesis of diaryl-1,2-diketones, and enable facile access to pharmaceutically important nitrogen heterocycles.

Publication Title

ChemistrySelect

Volume

6

Issue

19

First Page

4741

Last Page

4749

Digital Object Identifier (DOI)

10.1002/slct.202100505

E-ISSN

23656549

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