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Molecules 2018, 23(11), 2867; https://doi.org/10.3390/molecules23112867

Synthesis of Acridines through Alkyne Addition to Diarylamines

Department of Chemistry, University of St. Thomas, 2115 Summit Avenue, St. Paul, MN 55115, USA
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Academic Editor: Igor V. Alabugin
Received: 15 October 2018 / Revised: 30 October 2018 / Accepted: 31 October 2018 / Published: 3 November 2018
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)
Full-Text   |   PDF [654 KB, uploaded 3 November 2018]   |  

Abstract

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. View Full-Text
Keywords: cyclization; acridine; one-pot; terminal-alkyne; polycycles cyclization; acridine; one-pot; terminal-alkyne; polycycles
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Berger, K.E.; McCormick, G.M.; Jaye, J.A.; Rozeske, C.M.; Fort, E.H. Synthesis of Acridines through Alkyne Addition to Diarylamines. Molecules 2018, 23, 2867.

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