Synthesis of Acridines through Alkyne Addition to Diarylamines

Kristen E Berger; Grant M McCormick; Joseph A Jaye; Christina M Rozeske; Eric H Fort

doi:10.3390/molecules23112867

Synthesis of Acridines through Alkyne Addition to Diarylamines

Molecules. 2018 Nov 3;23(11):2867. doi: 10.3390/molecules23112867.

Authors

Kristen E Berger¹, Grant M McCormick², Joseph A Jaye³, Christina M Rozeske⁴, Eric H Fort⁵

Affiliations

¹ Department of Chemistry, University of St. Thomas, 2115 Summit Avenue, St. Paul, MN 55115, USA. berger46@purdue.edu.
² Department of Chemistry, University of St. Thomas, 2115 Summit Avenue, St. Paul, MN 55115, USA. grant.mccormick@unmc.edu.
³ Department of Chemistry, University of St. Thomas, 2115 Summit Avenue, St. Paul, MN 55115, USA. jaye4028@ucla.edu.
⁴ Department of Chemistry, University of St. Thomas, 2115 Summit Avenue, St. Paul, MN 55115, USA. christina.rozeske@gmail.com.
⁵ Department of Chemistry, University of St. Thomas, 2115 Summit Avenue, St. Paul, MN 55115, USA. ehfort@stthomas.edu.

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.

Keywords: acridine; cyclization; one-pot; polycycles; terminal-alkyne.

MeSH terms

Acridines / chemical synthesis*
Acridines / chemistry*
Alkynes / chemistry
Amines / chemistry*
Molecular Structure
Temperature

Substances

Acridines
Alkynes
Amines

Abstract

MeSH terms

Substances

Grants and funding