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Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

An efficient sequence based on the Ugi-azide reaction and rhodium(III)-catalyzed intermolecular annulation has been established for the preparation of tetrazole-isoquinolone/pyridone hybrids. Several N-acylaminomethyltetrazoles were reacted with arylacetylenes to form the hybrid products in moderate...

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Autores principales: Ojeda, Gerardo M, Ranjan, Prabhat, Fedoseev, Pavel, Amable, Lisandra, Sharma, Upendra K, Rivera, Daniel G, Van der Eycken, Erik V
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6808192/
https://www.ncbi.nlm.nih.gov/pubmed/31666879
http://dx.doi.org/10.3762/bjoc.15.237
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author Ojeda, Gerardo M
Ranjan, Prabhat
Fedoseev, Pavel
Amable, Lisandra
Sharma, Upendra K
Rivera, Daniel G
Van der Eycken, Erik V
author_facet Ojeda, Gerardo M
Ranjan, Prabhat
Fedoseev, Pavel
Amable, Lisandra
Sharma, Upendra K
Rivera, Daniel G
Van der Eycken, Erik V
author_sort Ojeda, Gerardo M
collection PubMed
description An efficient sequence based on the Ugi-azide reaction and rhodium(III)-catalyzed intermolecular annulation has been established for the preparation of tetrazole-isoquinolone/pyridone hybrids. Several N-acylaminomethyltetrazoles were reacted with arylacetylenes to form the hybrid products in moderate to very good yields. The method relies on the capacity of the rhodium catalyst to promote C(sp(2))–H activation in the presence of a suitable directing group. The Ugi-azide reaction provides broad molecular diversity and enables the introduction of the tetrazole moiety, which may further assist the catalytic reaction by coordinating the metal center. The scope of the isoquinolones is very wide and may be extended to the preparation of complex compounds having heterocyclic moieties such as pyridone, furan, thiophene and pyrrole, as well as the corresponding benzo-fused derivatives. The developed procedure is simple, reproducible and does not require inert conditions.
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spelling pubmed-68081922019-10-30 Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids Ojeda, Gerardo M Ranjan, Prabhat Fedoseev, Pavel Amable, Lisandra Sharma, Upendra K Rivera, Daniel G Van der Eycken, Erik V Beilstein J Org Chem Full Research Paper An efficient sequence based on the Ugi-azide reaction and rhodium(III)-catalyzed intermolecular annulation has been established for the preparation of tetrazole-isoquinolone/pyridone hybrids. Several N-acylaminomethyltetrazoles were reacted with arylacetylenes to form the hybrid products in moderate to very good yields. The method relies on the capacity of the rhodium catalyst to promote C(sp(2))–H activation in the presence of a suitable directing group. The Ugi-azide reaction provides broad molecular diversity and enables the introduction of the tetrazole moiety, which may further assist the catalytic reaction by coordinating the metal center. The scope of the isoquinolones is very wide and may be extended to the preparation of complex compounds having heterocyclic moieties such as pyridone, furan, thiophene and pyrrole, as well as the corresponding benzo-fused derivatives. The developed procedure is simple, reproducible and does not require inert conditions. Beilstein-Institut 2019-10-16 /pmc/articles/PMC6808192/ /pubmed/31666879 http://dx.doi.org/10.3762/bjoc.15.237 Text en Copyright © 2019, Ojeda 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
Ojeda, Gerardo M
Ranjan, Prabhat
Fedoseev, Pavel
Amable, Lisandra
Sharma, Upendra K
Rivera, Daniel G
Van der Eycken, Erik V
Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
title Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
title_full Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
title_fullStr Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
title_full_unstemmed Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
title_short Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
title_sort combining the ugi-azide multicomponent reaction and rhodium(iii)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6808192/
https://www.ncbi.nlm.nih.gov/pubmed/31666879
http://dx.doi.org/10.3762/bjoc.15.237
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