Issue 4, 2022, Issue in Progress

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

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

Supplementary files

Article information

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

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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