Issue 21, 2022

One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions

Abstract

A new one-pot and divergent synthesis of multisubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions was developed. The four-component reactions of 2-acylanilines, aldehydes, (carboxymethyl)(dimethyl)sulfonium bromides and isocyanides gave Ugi adducts, which were subsequently treated with DBU to produce polysubstituted quinolin-2(1H)-ones or oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones in good overall yields by intramolecular Knoevenagel condensation/hydrolysis or intramolecular Corey–Chaykovsky epoxidation reactions.

Graphical abstract: One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions

Supplementary files

Article information

Article type
Research Article
Submitted
14 Jul 2022
Accepted
15 Sep 2022
First published
16 Sep 2022

Org. Chem. Front., 2022,9, 5983-5988

One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions

M. Yang, H. Pan, H. Kong and M. Ding, Org. Chem. Front., 2022, 9, 5983 DOI: 10.1039/D2QO01130A

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