Issue 48, 2022

In situ generation of imines by the Staudinger/aza-Wittig tandem reaction combined with thermally induced Wolff rearrangement for one-pot three-component β-lactam synthesis

Abstract

A new efficient protocol for diastereoselective three-component one-pot lactam synthesis involving the in situ generation of imines via the Staudinger/aza-Wittig tandem reaction combined with the Wolff-rearrangement and ketene–imine cycloaddition was developed to produce a series of 24 novel structurally diverse β-lactam- or 1,3-oxazine-products. It was shown that this synthesis can be performed both as a two step-procedure and true MCR with simultaneous loading of all reactants. The intramolecular version of the 1st step provided facile access to seven-membered cyclic imines, which allowed further preparation of a series of rare tricyclic β-lactams. For the intermolecular version of the 1st step (acyclic imine generation), it was shown that the outcome of the synthesis is different from that using pre-synthesized and isolated imines. Additionally, this is the first example of the implementation of the Staudinger/aza-Wittig tandem reaction for the preparation of four-membered heterocycles.

Graphical abstract: In situ generation of imines by the Staudinger/aza-Wittig tandem reaction combined with thermally induced Wolff rearrangement for one-pot three-component β-lactam synthesis

Supplementary files

Article information

Article type
Paper
Submitted
10 Oct 2022
Accepted
14 Nov 2022
First published
15 Nov 2022

Org. Biomol. Chem., 2022,20, 9679-9683

In situ generation of imines by the Staudinger/aza-Wittig tandem reaction combined with thermally induced Wolff rearrangement for one-pot three-component β-lactam synthesis

P. Paramonova, R. Lebedev, O. Bakulina, D. Dar'in and M. Krasavin, Org. Biomol. Chem., 2022, 20, 9679 DOI: 10.1039/D2OB01852G

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