Synthesis of Acridines through Alkyne Addition to Diarylamines

A new synthesis of substituted acridines is achieved by palladium-catalyzed addition of terminal acetylenes between the aryl rings of bis(2-bromophenyl)amine. By including a diamine base and elevating the temperature, the reaction pathway favors the formation of acridine over a double Sonogashira re...

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Detalles Bibliográficos
Autores principales: Berger, Kristen E., McCormick, Grant M., Jaye, Joseph A., Rozeske, Christina M., Fort, Eric H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278640/
https://www.ncbi.nlm.nih.gov/pubmed/30400283
http://dx.doi.org/10.3390/molecules23112867
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author Berger, Kristen E.
McCormick, Grant M.
Jaye, Joseph A.
Rozeske, Christina M.
Fort, Eric H.
author_facet Berger, Kristen E.
McCormick, Grant M.
Jaye, Joseph A.
Rozeske, Christina M.
Fort, Eric H.
author_sort Berger, Kristen E.
collection PubMed
description A new synthesis of substituted acridines is achieved by palladium-catalyzed addition of terminal acetylenes between the aryl rings of bis(2-bromophenyl)amine. By including a diamine base and elevating the temperature, the reaction pathway favors the formation of acridine over a double Sonogashira reaction to form bis(tolan)amine. This method is demonstrated with several aryl-alkynes and alkyl-alkynes.
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spelling pubmed-62786402018-12-13 Synthesis of Acridines through Alkyne Addition to Diarylamines Berger, Kristen E. McCormick, Grant M. Jaye, Joseph A. Rozeske, Christina M. Fort, Eric H. Molecules Article A new synthesis of substituted acridines is achieved by palladium-catalyzed addition of terminal acetylenes between the aryl rings of bis(2-bromophenyl)amine. By including a diamine base and elevating the temperature, the reaction pathway favors the formation of acridine over a double Sonogashira reaction to form bis(tolan)amine. This method is demonstrated with several aryl-alkynes and alkyl-alkynes. MDPI 2018-11-03 /pmc/articles/PMC6278640/ /pubmed/30400283 http://dx.doi.org/10.3390/molecules23112867 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Berger, Kristen E.
McCormick, Grant M.
Jaye, Joseph A.
Rozeske, Christina M.
Fort, Eric H.
Synthesis of Acridines through Alkyne Addition to Diarylamines
title Synthesis of Acridines through Alkyne Addition to Diarylamines
title_full Synthesis of Acridines through Alkyne Addition to Diarylamines
title_fullStr Synthesis of Acridines through Alkyne Addition to Diarylamines
title_full_unstemmed Synthesis of Acridines through Alkyne Addition to Diarylamines
title_short Synthesis of Acridines through Alkyne Addition to Diarylamines
title_sort synthesis of acridines through alkyne addition to diarylamines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278640/
https://www.ncbi.nlm.nih.gov/pubmed/30400283
http://dx.doi.org/10.3390/molecules23112867
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