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

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]triazol...

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Autores principales: Ganai, Ab Majeed, Pathan, Tabasum Khan, Sayyad, Nisar, Kushwaha, Babita, Kushwaha, Narva Deshwar, Tzakos, Andreas G., Karpoormath, Rajshekhar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8979044/
https://www.ncbi.nlm.nih.gov/pubmed/35425261
http://dx.doi.org/10.1039/d1ra07749j
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author Ganai, Ab Majeed
Pathan, Tabasum Khan
Sayyad, Nisar
Kushwaha, Babita
Kushwaha, Narva Deshwar
Tzakos, Andreas G.
Karpoormath, Rajshekhar
author_facet Ganai, Ab Majeed
Pathan, Tabasum Khan
Sayyad, Nisar
Kushwaha, Babita
Kushwaha, Narva Deshwar
Tzakos, Andreas G.
Karpoormath, Rajshekhar
author_sort Ganai, Ab Majeed
collection PubMed
description 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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spelling pubmed-89790442022-04-13 DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement Ganai, Ab Majeed Pathan, Tabasum Khan Sayyad, Nisar Kushwaha, Babita Kushwaha, Narva Deshwar Tzakos, Andreas G. Karpoormath, Rajshekhar RSC Adv Chemistry 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%). The Royal Society of Chemistry 2022-01-12 /pmc/articles/PMC8979044/ /pubmed/35425261 http://dx.doi.org/10.1039/d1ra07749j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Ganai, Ab Majeed
Pathan, Tabasum Khan
Sayyad, Nisar
Kushwaha, Babita
Kushwaha, Narva Deshwar
Tzakos, Andreas G.
Karpoormath, Rajshekhar
DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement
title DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement
title_full DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement
title_fullStr DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement
title_full_unstemmed DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement
title_short DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement
title_sort dbu mediated one-pot synthesis of triazolo triazines via dimroth type rearrangement
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8979044/
https://www.ncbi.nlm.nih.gov/pubmed/35425261
http://dx.doi.org/10.1039/d1ra07749j
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