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Synlett
DOI: 10.1055/a-2604-4702
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Oxone-Mediated Mild Removal of an Azine Protecting/Directing Group for Applications in Organic Synthesis

Gokul Ganesan‡
a   National Center for Nanosciences and Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, India
c   Department of Chemistry, Jai Hind College Autonomous, ‘A’ Road, Churchgate, Mumbai 400020, Maharashtra, India
,
Pownthurai Balasubramaniam‡
a   National Center for Nanosciences and Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, India
,
Mukeshkumar Yadav‡
a   National Center for Nanosciences and Nanotechnology, University of Mumbai, Vidyanagari, Mumbai 400098, Maharashtra, India
,
Hardik Janwadkar
b   Department of Chemistry, Institute of Chemical Technology, N.P. Marg, Matunga, Mumbai 400019, India
,
Abhijit Papalkar
d   Department of Chemistry, Fergusson College, F.C. Road, Pune 411004, Maharashtra, India
,
Atul Chaskar∗
b   Department of Chemistry, Institute of Chemical Technology, N.P. Marg, Matunga, Mumbai 400019, India
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Abstract

Azine derivatives of carbonyl compounds are used as protecting groups and have recently been utilized as directing groups in C–H activation. The stability of the azine functional group limits its application in areas where its subsequent removal is desirable. We herein report a mild and efficient method for removal of an azine group using Oxone as a green oxidant in the presence of an acetone/water solvent system. Carbonyl regeneration occurs in high yields from a range of aldazine and ketazine derivatives. A gram-scale synthesis and removal of the azine directing group from an ortho-functionalized azine are performed to extend the application of this methodology.

Key words

azines - oxidative deprotection - Oxone - directing groups - carbonyl compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2604-4702.
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Publication History

Received: 02 February 2025

Accepted after revision: 08 May 2025

Accepted Manuscript online:
08 May 2025

Article published online:
03 July 2025

© 2025. Thieme. All rights reserved

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