Issue 36, 2023

Microwave-assisted chemoselective synthesis and photophysical properties of 2-arylazo-biphenyl-4-carboxamides from hydrazonals

Abstract

The reaction of 3-oxo-2-arylhydrazonopropanals with acetoacetanilide in an equimolar ratio, under DBU/1,4-dioxane/microwave irradiation reaction conditions, resulted in chemoselective formation of 4-arylazo-5-hydroxy-benzamide derivatives. The structures of the obtained biphenyl-4-carboxamides were characterized by several spectroscopic techniques including IR, 1H- and 13C-NMR, MS and HRMS, and X-ray single crystals of three examples. The photophysical properties of the new products were also evaluated, with a particular focus on their absorption and emission spectra, which provided valuable information regarding their optical properties. The new compounds emitted 513–549 nm green fluorescence in acetone solution under UV irradiation.

Graphical abstract: Microwave-assisted chemoselective synthesis and photophysical properties of 2-arylazo-biphenyl-4-carboxamides from hydrazonals

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
08 Jul 2023
Accepted
07 Aug 2023
First published
22 Aug 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 25054-25068

Microwave-assisted chemoselective synthesis and photophysical properties of 2-arylazo-biphenyl-4-carboxamides from hydrazonals

A. M. Alazemi, K. M. Dawood, H. M. Al-Matar and W. M. Tohamy, RSC Adv., 2023, 13, 25054 DOI: 10.1039/D3RA04558G

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