Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids

Readily available 4-bromobenzo[c][2,7]naphthyridine undergoes regioselective direct ring metalation at C-5 with TMPMgCl∙LiCl at −40 °C. Quenching with various electrophiles gives a broad range of 5-substituted products, which are building blocks for the synthesis of heterocyclic natural products and...

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Detalles Bibliográficos
Autores principales: Melzer, Benedikt C, Plodek, Alois, Bracher, Franz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6774065/
https://www.ncbi.nlm.nih.gov/pubmed/31598182
http://dx.doi.org/10.3762/bjoc.15.222
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author Melzer, Benedikt C
Plodek, Alois
Bracher, Franz
author_facet Melzer, Benedikt C
Plodek, Alois
Bracher, Franz
author_sort Melzer, Benedikt C
collection PubMed
description Readily available 4-bromobenzo[c][2,7]naphthyridine undergoes regioselective direct ring metalation at C-5 with TMPMgCl∙LiCl at −40 °C. Quenching with various electrophiles gives a broad range of 5-substituted products, which are building blocks for the synthesis of heterocyclic natural products and analogues thereof. In combination with a Parham-type cyclization a novel approach to pyrido[4,3,2-mn]acridones has been worked out.
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spelling pubmed-67740652019-10-09 Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids Melzer, Benedikt C Plodek, Alois Bracher, Franz Beilstein J Org Chem Full Research Paper Readily available 4-bromobenzo[c][2,7]naphthyridine undergoes regioselective direct ring metalation at C-5 with TMPMgCl∙LiCl at −40 °C. Quenching with various electrophiles gives a broad range of 5-substituted products, which are building blocks for the synthesis of heterocyclic natural products and analogues thereof. In combination with a Parham-type cyclization a novel approach to pyrido[4,3,2-mn]acridones has been worked out. Beilstein-Institut 2019-09-26 /pmc/articles/PMC6774065/ /pubmed/31598182 http://dx.doi.org/10.3762/bjoc.15.222 Text en Copyright © 2019, Melzer 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
Melzer, Benedikt C
Plodek, Alois
Bracher, Franz
Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids
title Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids
title_full Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids
title_fullStr Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids
title_full_unstemmed Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids
title_short Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids
title_sort functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. a novel approach to analogues of pyridoacridine alkaloids
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6774065/
https://www.ncbi.nlm.nih.gov/pubmed/31598182
http://dx.doi.org/10.3762/bjoc.15.222
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