Issue 33, 2022, Issue in Progress
From the journal:

RSC Advances

Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols†

Haiting Yin, ORCID logo a   Yunjun Wu,a   Xiaoxia Gu,a   Zhijun Feng,a   Meifang Wang,ab   Dexiang Feng,a   Ming Wang,a   Ziyang Chenga  and  Shaoyin Wang ORCID logo *ab  

* Corresponding authors

a Department of Chemistry, Institute of Synthesis and Application of Medical Materials, Chunhui Scientific Research Interest Group, Wannan Medical College, Wuhu 241002, China

b The Key Laboratory of Antiinflammatory and Immune Medicine, Ministry of Education, Anhui Medical University, Hefei 230032, China
E-mail: wsychem@163.com

Abstract

Two acid-catalyzed tandem reactions between 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols are described. Depending mainly on the propargylic alcohol used, these tandem reactions proceed via either a Friedel–Crafts-type allenylation followed by 6-endo-dig cyclization sequence to form pyrano[3,2-c]quinolones or a Friedel–Crafts-type alkylation and 5-exo-dig ring closure sequence to afford furo[3,2-c]quinolones in moderate-to-high yields. The pyrano[3,2-c]quinolones products could be further transformed to tetracyclic 4,9-dihydro-5H-cyclopenta[lmn]phenanthridin-5-one derivatives.

Graphical abstract: Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D2RA03416F
Article type
Paper
Submitted
01 Jun 2022
Accepted
17 Jul 2022
First published
21 Jul 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 21066-21078

Permissions

Request permissions

Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols

H. Yin, Y. Wu, X. Gu, Z. Feng, M. Wang, D. Feng, M. Wang, Z. Cheng and S. Wang, RSC Adv., 2022, 12, 21066 DOI: 10.1039/D2RA03416F

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