Issue 2, 2021

Palladium-catalyzed cascade reactions in aqueous media: synthesis and photophysical properties of pyrazino-fused quinazolinones

Abstract

Heterocycle-fused quinazolinone derivatives have attracted great attention due to their diversified biological and optical activities. In this study, a novel one-pot palladium-catalyzed cascade C–C coupling/cyclization/aromatization of 2-(4-oxoquinazolin-3(4H)-yl)acetonitrile derivatives with arylboronic acids has been disclosed to synthesize 1,3-diaryl-6H-pyrazino[2,1-b]quinazolin-6-one in water. This protocol provides an efficient access to valuable pyrazino-fused quinazolinones in a green solvent (i.e., water) with yields ranging from moderate to excellent. Furthermore, the photophysical properties of these molecules were investigated. The resultant pyrazino-fused quinazolinones exhibit tunable fluorescence, and 3e displays the aggregation induced emission properties with a large Stokes shift. This study provides a useful approach to the development of pyrazino-fused quinazolinones, which have potential applications in chemistry, biology, and materials science.

Graphical abstract: Palladium-catalyzed cascade reactions in aqueous media: synthesis and photophysical properties of pyrazino-fused quinazolinones

Supplementary files

Article information

Article type
Research Article
Submitted
09 Oct 2020
Accepted
21 Nov 2020
First published
23 Nov 2020

Org. Chem. Front., 2021,8, 304-309

Palladium-catalyzed cascade reactions in aqueous media: synthesis and photophysical properties of pyrazino-fused quinazolinones

Y. Zhang, W. Xiong, L. Chen, Y. Shao, R. Li, Z. Chen, J. Ge, N. Lv and J. Chen, Org. Chem. Front., 2021, 8, 304 DOI: 10.1039/D0QO01244K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements