Issue 4, 2022, Issue in Progress
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RSC Advances

DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement†

Ab Majeed Ganai,a   Tabasum Khan Pathan,a   Nisar Sayyad,a   Babita Kushwaha,a   Narva Deshwar Kushwaha,a   Andreas G. Tzakosb  and  Rajshekhar Karpoormath ORCID logo *a  

* Corresponding authors

a Department of Pharmaceutical Chemistry, Discipline of Pharmaceutical Sciences, College of Health Sciences, University of KwaZulu-Natal (Westville), Durban 4000, South Africa
E-mail: karpoormath@ukzn.ac.za

b Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, Ioannina, Greece

Abstract

Herein we report an efficient one-pot synthesis of [1,2,4]triazolo[1,5 a][1,3,5]triazines from commercially available substituted aryl/heteroaryl aldehydes and substituted 2-hydrazinyl-1,3,5-triazines via N-bromosuccinimide (NBS) mediated oxidative C–N bond formation. Isomerisation of [1,2,4]triazolo[4,3-a][1,3,5]triazines to [1,2,4]triazolo[1,5-a][1,3,5]triazines is driven by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) affording both isomers with good to excellent yields (70–96%).

Graphical abstract: DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement

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Article information

DOI
https://doi.org/10.1039/D1RA07749J
Article type
Paper
Submitted
20 Oct 2021
Accepted
11 Dec 2021
First published
12 Jan 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 2102-2106

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DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement

A. M. Ganai, T. K. Pathan, N. Sayyad, B. Kushwaha, N. D. Kushwaha, A. G. Tzakos and R. Karpoormath, RSC Adv., 2022, 12, 2102 DOI: 10.1039/D1RA07749J

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