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Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes

We describe the synthesis of so far synthetically not accessible 3,6-substituted-4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines as nitrogen-rich heterocycles. The target compounds were obtained in five steps, including an amidation and a cyclative cleavage reaction as key reaction steps. The introdu...

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Autores principales: Wippert, Nicolai, Nieger, Martin, Herlan, Claudine, Jung, Nicole, Bräse, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8630434/
https://www.ncbi.nlm.nih.gov/pubmed/34900007
http://dx.doi.org/10.3762/bjoc.17.187
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author Wippert, Nicolai
Nieger, Martin
Herlan, Claudine
Jung, Nicole
Bräse, Stefan
author_facet Wippert, Nicolai
Nieger, Martin
Herlan, Claudine
Jung, Nicole
Bräse, Stefan
author_sort Wippert, Nicolai
collection PubMed
description We describe the synthesis of so far synthetically not accessible 3,6-substituted-4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines as nitrogen-rich heterocycles. The target compounds were obtained in five steps, including an amidation and a cyclative cleavage reaction as key reaction steps. The introduction of two side chains allowed a variation of the pyrazolo[3,4-d][1,2,3]triazine core with commercially available building blocks, enabling the extension of the protocol to gain other derivatives straightforwardly. Attempts to synthesize 3,7-substituted-4,7-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, the regioisomers of the successfully gained 3,6-substituted 4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, were not successful under similar conditions due to the higher stability of the triazene functionality in the regioisomeric precursors and thus, the failure of the removal of the protective group.
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spelling pubmed-86304342021-12-09 Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes Wippert, Nicolai Nieger, Martin Herlan, Claudine Jung, Nicole Bräse, Stefan Beilstein J Org Chem Full Research Paper We describe the synthesis of so far synthetically not accessible 3,6-substituted-4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines as nitrogen-rich heterocycles. The target compounds were obtained in five steps, including an amidation and a cyclative cleavage reaction as key reaction steps. The introduction of two side chains allowed a variation of the pyrazolo[3,4-d][1,2,3]triazine core with commercially available building blocks, enabling the extension of the protocol to gain other derivatives straightforwardly. Attempts to synthesize 3,7-substituted-4,7-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, the regioisomers of the successfully gained 3,6-substituted 4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, were not successful under similar conditions due to the higher stability of the triazene functionality in the regioisomeric precursors and thus, the failure of the removal of the protective group. Beilstein-Institut 2021-11-22 /pmc/articles/PMC8630434/ /pubmed/34900007 http://dx.doi.org/10.3762/bjoc.17.187 Text en Copyright © 2021, Wippert et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Wippert, Nicolai
Nieger, Martin
Herlan, Claudine
Jung, Nicole
Bräse, Stefan
Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
title Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
title_full Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
title_fullStr Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
title_full_unstemmed Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
title_short Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
title_sort synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8630434/
https://www.ncbi.nlm.nih.gov/pubmed/34900007
http://dx.doi.org/10.3762/bjoc.17.187
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