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DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement. 2022
Ab Majeed Ganai, and
Tabasum Khan Pathan, and
Nisar Sayyad, and
Babita Kushwaha, and
Narva Deshwar Kushwaha, and
Andreas G Tzakos, and
Rajshekhar Karpoormath
Department of Pharmaceutical Chemistry, Discipline of Pharmaceutical Sciences, College of Health Sciences, University of KwaZulu-Natal (Westville) Durban 4000 South Africa karpoormath@ukzn.ac.za.
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%).
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