Download PDF
Synlett
DOI: 10.1055/a-2604-4702
letter

OXONE MEDIATED MILD REMOVAL OF AZINE PROTECTING/ DIRECTING GROUP FOR APPLICATION IN ORGANIC SYNTHESES

Gokul Ganesan
1   National Centre for Nanosciences and Nanotechnology, University of Mumbai, MUMBAI, India (Ringgold ID: RIN29396)
2   Department of Chemistry, Jai Hind College, Mumbai, India (Ringgold ID: RIN210758)
,
Pownthurai Balasubramaniam
3   National Centre for Nanosciences and Nanotechnology, University of Mumbai, Mumbai, India (Ringgold ID: RIN29396)
,
Mukeshkumar Yadav
3   National Centre for Nanosciences and Nanotechnology, University of Mumbai, Mumbai, India (Ringgold ID: RIN29396)
,
Hardik Janwadkar
4   Department of Chemistry, Mumbai University Institute of Chemical Technology, Mumbai, India (Ringgold ID: RIN80493)
,
Abhijit Papalkar
5   Department of Chemistry, Fergusson College, Pune, India (Ringgold ID: RIN209969)
,
Atul Changdev Chaskar
4   Department of Chemistry, Mumbai University Institute of Chemical Technology, Mumbai, India (Ringgold ID: RIN80493)
› Author Affiliations
› Further Information
 PDF Download All articles of this category

Abstract Azine derivatives of carbonyl compounds have been used as protecting groups in the past and as directing groups in CH activation recently. Stability of the azine functional groups limits its application in areas where removal of the group is desirable. We hereby report a mild and efficient removal of the azine group using a green oxidant oxone in the presence of acetone water solvent system. The carbonyl regeneration has been afforded in high yields from a range of aldazine and ketazine derivatives to demonstrate the substrate scope. Gram scale synthesis and removal of azine DG from an ortho functionalized azine has been performed to extend the application of the methodology.



Publication History

Received: 02 February 2025

Accepted after revision: 08 May 2025

Accepted Manuscript online:
08 May 2025

© . Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany