Issue 16, 2024

Catalyst-free synthesis of hydrazino-containing glycine derivatives via a diaziridine in situ formation/ring-opening cascade

Abstract

Glycine derivatives are prevalent structural motifs that can be easily found in many bioactive molecules and natural isolates. To date, chemical synthesis of hydrazino-containing glycine derivatives has mainly focused on the utilization of metal catalysts or light-irradiation methods. Herein, we report a three-component reaction of amines, azodicarboxylates, and diazoalkanes under green and sustainable reaction conditions, leading to a wide range of hydrazino-containing glycine derivatives in good to excellent yields. Compared to the reported methods, the as-developed method does not require catalysts or light irradiation. The success of the scale-up reaction, synthetic transformation of the formed glycine products, and the direct aqueous media synthesis further rendered the method attractive and valuable. Control experiments together with detailed mechanism studies revealed that the in situ formed diaziridines are the key reaction intermediates.

Graphical abstract: Catalyst-free synthesis of hydrazino-containing glycine derivatives via a diaziridine in situ formation/ring-opening cascade

Supplementary files

Article information

Article type
Communication
Submitted
26 May 2024
Accepted
11 Jul 2024
First published
12 Jul 2024

Green Chem., 2024,26, 9104-9109

Catalyst-free synthesis of hydrazino-containing glycine derivatives via a diaziridine in situ formation/ring-opening cascade

C. Rong, Q. Li and J. Xuan, Green Chem., 2024, 26, 9104 DOI: 10.1039/D4GC02565B

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