Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Dzieszkowski, Krzysztof, Barańska, Izabela, Rafiński, Zbigniew
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
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
_version_ 1783600899425304576
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
work_keys_str_mv AT dzieszkowskikrzysztof constructionofdihydropyrido23dpyrimidinescaffoldsviaazaclaisenrearrangementcatalyzedbynheterocycliccarbenes
AT baranskaizabela constructionofdihydropyrido23dpyrimidinescaffoldsviaazaclaisenrearrangementcatalyzedbynheterocycliccarbenes
AT rafinskizbigniew constructionofdihydropyrido23dpyrimidinescaffoldsviaazaclaisenrearrangementcatalyzedbynheterocycliccarbenes