Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt

A synthesis of fluorinated pyrimidines under mild conditions from amidine hydrochlorides and the recently described potassium 2-cyano-2-fluoroethenolate was developed. A broad substrate scope was tested and mostly excellent yields were obtained. The synthesis of fluorinated aminopyrazoles from the s...

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Detalles Bibliográficos
Autores principales: Lucas, Tobias, Dietz, Jule-Philipp, Opatz, Till
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7113542/
https://www.ncbi.nlm.nih.gov/pubmed/32273906
http://dx.doi.org/10.3762/bjoc.16.41
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author Lucas, Tobias
Dietz, Jule-Philipp
Opatz, Till
author_facet Lucas, Tobias
Dietz, Jule-Philipp
Opatz, Till
author_sort Lucas, Tobias
collection PubMed
description A synthesis of fluorinated pyrimidines under mild conditions from amidine hydrochlorides and the recently described potassium 2-cyano-2-fluoroethenolate was developed. A broad substrate scope was tested and mostly excellent yields were obtained. The synthesis of fluorinated aminopyrazoles from the same fluorinated precursor could be demonstrated but proceeded with lower efficiency.
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spelling pubmed-71135422020-04-09 Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt Lucas, Tobias Dietz, Jule-Philipp Opatz, Till Beilstein J Org Chem Full Research Paper A synthesis of fluorinated pyrimidines under mild conditions from amidine hydrochlorides and the recently described potassium 2-cyano-2-fluoroethenolate was developed. A broad substrate scope was tested and mostly excellent yields were obtained. The synthesis of fluorinated aminopyrazoles from the same fluorinated precursor could be demonstrated but proceeded with lower efficiency. Beilstein-Institut 2020-03-20 /pmc/articles/PMC7113542/ /pubmed/32273906 http://dx.doi.org/10.3762/bjoc.16.41 Text en Copyright © 2020, Lucas et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Lucas, Tobias
Dietz, Jule-Philipp
Opatz, Till
Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
title Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
title_full Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
title_fullStr Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
title_full_unstemmed Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
title_short Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
title_sort synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7113542/
https://www.ncbi.nlm.nih.gov/pubmed/32273906
http://dx.doi.org/10.3762/bjoc.16.41
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