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Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes
[Image: see text] N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of α,β-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NH...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7590975/ https://www.ncbi.nlm.nih.gov/pubmed/32312044 http://dx.doi.org/10.1021/acs.joc.0c00657 |
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author | Dzieszkowski, Krzysztof Barańska, Izabela Rafiński, Zbigniew |
author_facet | Dzieszkowski, Krzysztof Barańska, Izabela Rafiński, Zbigniew |
author_sort | Dzieszkowski, Krzysztof |
collection | PubMed |
description | [Image: see text] N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of α,β-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NHC-activation-based path with the use of 6-aminouracils as stable α,β-diEWG cyclic vinylogous amides for the efficient synthesis of bicyclic N-unprotected lactams similar to those in many useful drugs. |
format | Online Article Text |
id | pubmed-7590975 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-75909752020-10-28 Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes Dzieszkowski, Krzysztof Barańska, Izabela Rafiński, Zbigniew J Org Chem [Image: see text] N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of α,β-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NHC-activation-based path with the use of 6-aminouracils as stable α,β-diEWG cyclic vinylogous amides for the efficient synthesis of bicyclic N-unprotected lactams similar to those in many useful drugs. American Chemical Society 2020-04-21 2020-05-15 /pmc/articles/PMC7590975/ /pubmed/32312044 http://dx.doi.org/10.1021/acs.joc.0c00657 Text en This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Dzieszkowski, Krzysztof Barańska, Izabela Rafiński, Zbigniew Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes |
title | Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed
by N-Heterocyclic Carbenes |
title_full | Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed
by N-Heterocyclic Carbenes |
title_fullStr | Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed
by N-Heterocyclic Carbenes |
title_full_unstemmed | Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed
by N-Heterocyclic Carbenes |
title_short | Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed
by N-Heterocyclic Carbenes |
title_sort | construction of dihydropyrido[2,3-d]pyrimidine scaffolds via aza-claisen rearrangement catalyzed
by n-heterocyclic carbenes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7590975/ https://www.ncbi.nlm.nih.gov/pubmed/32312044 http://dx.doi.org/10.1021/acs.joc.0c00657 |
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