A three-component, Zn(OTf)(2)-mediated entry into trisubstituted 2-aminoimidazoles

A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)(2)-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported base-promoted unimolecular cyclization of propargylu...

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Detalles Bibliográficos
Autores principales: Lukin, Alexei, Bakholdina, Anna, Kryukova, Anna, Sapegin, Alexander, Krasavin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6541334/
https://www.ncbi.nlm.nih.gov/pubmed/31164943
http://dx.doi.org/10.3762/bjoc.15.103
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author Lukin, Alexei
Bakholdina, Anna
Kryukova, Anna
Sapegin, Alexander
Krasavin, Mikhail
author_facet Lukin, Alexei
Bakholdina, Anna
Kryukova, Anna
Sapegin, Alexander
Krasavin, Mikhail
author_sort Lukin, Alexei
collection PubMed
description A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)(2)-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported base-promoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.
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spelling pubmed-65413342019-06-04 A three-component, Zn(OTf)(2)-mediated entry into trisubstituted 2-aminoimidazoles Lukin, Alexei Bakholdina, Anna Kryukova, Anna Sapegin, Alexander Krasavin, Mikhail Beilstein J Org Chem Letter A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)(2)-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported base-promoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines. Beilstein-Institut 2019-05-07 /pmc/articles/PMC6541334/ /pubmed/31164943 http://dx.doi.org/10.3762/bjoc.15.103 Text en Copyright © 2019, Lukin 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 Letter
Lukin, Alexei
Bakholdina, Anna
Kryukova, Anna
Sapegin, Alexander
Krasavin, Mikhail
A three-component, Zn(OTf)(2)-mediated entry into trisubstituted 2-aminoimidazoles
title A three-component, Zn(OTf)(2)-mediated entry into trisubstituted 2-aminoimidazoles
title_full A three-component, Zn(OTf)(2)-mediated entry into trisubstituted 2-aminoimidazoles
title_fullStr A three-component, Zn(OTf)(2)-mediated entry into trisubstituted 2-aminoimidazoles
title_full_unstemmed A three-component, Zn(OTf)(2)-mediated entry into trisubstituted 2-aminoimidazoles
title_short A three-component, Zn(OTf)(2)-mediated entry into trisubstituted 2-aminoimidazoles
title_sort three-component, zn(otf)(2)-mediated entry into trisubstituted 2-aminoimidazoles
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6541334/
https://www.ncbi.nlm.nih.gov/pubmed/31164943
http://dx.doi.org/10.3762/bjoc.15.103
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