Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds

The condensation of 5-alkoxycarbonyl-1H-pyrrolediones with cyclic ketazinones was systematically investigated. It was discovered that the regioselectivity of this reaction can be easily swapped between two alternative directions affording derivatives of partially hydrogenated indole or benzofurane....

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Detalles Bibliográficos
Autores principales: Dubovtsev, Alexey Yu, Dmitriev, Maksim V, Maslivets, Аndrey N, Rubin, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5669231/
https://www.ncbi.nlm.nih.gov/pubmed/29114325
http://dx.doi.org/10.3762/bjoc.13.218
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author Dubovtsev, Alexey Yu
Dmitriev, Maksim V
Maslivets, Аndrey N
Rubin, Michael
author_facet Dubovtsev, Alexey Yu
Dmitriev, Maksim V
Maslivets, Аndrey N
Rubin, Michael
author_sort Dubovtsev, Alexey Yu
collection PubMed
description The condensation of 5-alkoxycarbonyl-1H-pyrrolediones with cyclic ketazinones was systematically investigated. It was discovered that the regioselectivity of this reaction can be easily swapped between two alternative directions affording derivatives of partially hydrogenated indole or benzofurane. The control of this regioselectivity is efficiently governed by steric effects at the hydrazone moiety of the ketazinone reagent.
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spelling pubmed-56692312017-11-07 Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds Dubovtsev, Alexey Yu Dmitriev, Maksim V Maslivets, Аndrey N Rubin, Michael Beilstein J Org Chem Full Research Paper The condensation of 5-alkoxycarbonyl-1H-pyrrolediones with cyclic ketazinones was systematically investigated. It was discovered that the regioselectivity of this reaction can be easily swapped between two alternative directions affording derivatives of partially hydrogenated indole or benzofurane. The control of this regioselectivity is efficiently governed by steric effects at the hydrazone moiety of the ketazinone reagent. Beilstein-Institut 2017-10-19 /pmc/articles/PMC5669231/ /pubmed/29114325 http://dx.doi.org/10.3762/bjoc.13.218 Text en Copyright © 2017, Dubovtsev 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), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 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
Dubovtsev, Alexey Yu
Dmitriev, Maksim V
Maslivets, Аndrey N
Rubin, Michael
Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_full Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_fullStr Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_full_unstemmed Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_short Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
title_sort regiodivergent condensation of 5-alkoxycarbonyl-1h-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5669231/
https://www.ncbi.nlm.nih.gov/pubmed/29114325
http://dx.doi.org/10.3762/bjoc.13.218
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