TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes

The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki‐coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel‐Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS‐ethynyl)‐substituted n...

Descripción completa

Detalles Bibliográficos
Autores principales: Ahrens, Lukas, Maier, Steffen, Misselwitz, Erik, Oeser, Thomas, Rominger, Frank, Freudenberg, Jan, Bunz, Uwe H. F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362069/
https://www.ncbi.nlm.nih.gov/pubmed/33938059
http://dx.doi.org/10.1002/chem.202101246
_version_ 1783738080634601472
author Ahrens, Lukas
Maier, Steffen
Misselwitz, Erik
Oeser, Thomas
Rominger, Frank
Freudenberg, Jan
Bunz, Uwe H. F.
author_facet Ahrens, Lukas
Maier, Steffen
Misselwitz, Erik
Oeser, Thomas
Rominger, Frank
Freudenberg, Jan
Bunz, Uwe H. F.
author_sort Ahrens, Lukas
collection PubMed
description The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki‐coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel‐Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS‐ethynyl)‐substituted naphtha[1,8‐gh:5,4‐g′h′]diquinoline and naphtho[1,8‐bc:5,4‐b′c′]diacridine. Nitrogen incorporation stabilizes the bisacenes with respect to oxidation compared to their consanguine nonaza analogs.
format Online
Article
Text
id pubmed-8362069
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-83620692021-08-17 TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes Ahrens, Lukas Maier, Steffen Misselwitz, Erik Oeser, Thomas Rominger, Frank Freudenberg, Jan Bunz, Uwe H. F. Chemistry Communications The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki‐coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel‐Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS‐ethynyl)‐substituted naphtha[1,8‐gh:5,4‐g′h′]diquinoline and naphtho[1,8‐bc:5,4‐b′c′]diacridine. Nitrogen incorporation stabilizes the bisacenes with respect to oxidation compared to their consanguine nonaza analogs. John Wiley and Sons Inc. 2021-05-27 2021-07-21 /pmc/articles/PMC8362069/ /pubmed/33938059 http://dx.doi.org/10.1002/chem.202101246 Text en © 2021 The Authors. Published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Ahrens, Lukas
Maier, Steffen
Misselwitz, Erik
Oeser, Thomas
Rominger, Frank
Freudenberg, Jan
Bunz, Uwe H. F.
TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes
title TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes
title_full TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes
title_fullStr TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes
title_full_unstemmed TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes
title_short TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes
title_sort tips‐ethynylated naphthodiquinoline and naphthodiacridine: novel diazabisacenes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362069/
https://www.ncbi.nlm.nih.gov/pubmed/33938059
http://dx.doi.org/10.1002/chem.202101246
work_keys_str_mv AT ahrenslukas tipsethynylatednaphthodiquinolineandnaphthodiacridinenoveldiazabisacenes
AT maiersteffen tipsethynylatednaphthodiquinolineandnaphthodiacridinenoveldiazabisacenes
AT misselwitzerik tipsethynylatednaphthodiquinolineandnaphthodiacridinenoveldiazabisacenes
AT oeserthomas tipsethynylatednaphthodiquinolineandnaphthodiacridinenoveldiazabisacenes
AT romingerfrank tipsethynylatednaphthodiquinolineandnaphthodiacridinenoveldiazabisacenes
AT freudenbergjan tipsethynylatednaphthodiquinolineandnaphthodiacridinenoveldiazabisacenes
AT bunzuwehf tipsethynylatednaphthodiquinolineandnaphthodiacridinenoveldiazabisacenes

Ejemplares similares