Issue 28, 2019
From the journal:

RSC Advances

Aerobic, metal-free synthesis of 6H-chromeno[4,3-b]quinolin-6-ones†

Nhan N. H. Ton,a   Ha V. Dang,a   Nam T. S. Phan ORCID logo a  and  Tung T. Nguyen ORCID logo *a  

* Corresponding authors

a Faculty of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam
E-mail: tungtn@hcmut.edu.vn

Abstract

A Friedländer-based method for transition-metal free, aerobic synthesis of chromene-fused quinolinones is reported. The coupling of 4-hydrocoumarins and 2-aminobenzyl alcohols proceeds in the presence of acetic acid solvent and oxygen oxidant, affording 6H-chromeno[4,3-b]quinolin-6-ones in good to excellent yields. The reactions are tolerant of functionalities such as alkyl, methoxy, bromo, chloro, and N-heterocycle. Isosteric cyclic 1,3-diketones and 2-amino acetophenones also give fused quinolinones under reaction conditions. The method herein offers a rapid and benign synthesis of hitherto challenging N-heterocycles. To our best knowledge, such a convenient pathway to obtain chromene-fused quinolinones have not been known in the literature.

Graphical abstract: Aerobic, metal-free synthesis of 6H-chromeno[4,3-b]quinolin-6-ones

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C9RA02267H
Article type
Paper
Submitted
25 Mar 2019
Accepted
17 May 2019
First published
23 May 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 16215-16222

Permissions

Request permissions

Aerobic, metal-free synthesis of 6H-chromeno[4,3-b]quinolin-6-ones

Nhan N. H. Ton, H. V. Dang, N. T. S. Phan and T. T. Nguyen, RSC Adv., 2019, 9, 16215 DOI: 10.1039/C9RA02267H

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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