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

Authors

Suraj M. Sutar, Karnatak University
Pavankumar Prabhala, Karnatak University
Hemantkumar M. Savanur, P.C. Jabin Science College
Rajesh G. Kalkhambkar, Karnatak University
Gopalakrishnan Aridoss, Ltd.Follow
Kenneth K. Laali, University of North FloridaFollow

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

Citation Information

Sutar, Prabhala, P., Savanur, H. M., Kalkhambkar, R. G., Aridoss, G., & Laali, K. K. (2021). 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. ChemistrySelect., 6(19), 4741–4749. https://doi.org/10.1002/slct.202100505