scholarly journals Synthesis of Acridines through Alkyne Addition to Diarylamines

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2867 ◽  
Author(s):  
Kristen Berger ◽  
Grant McCormick ◽  
Joseph Jaye ◽  
Christina Rozeske ◽  
Eric Fort
Keyword(s):  
Reaction Pathway ◽  
Sonogashira Reaction ◽  
New Synthesis ◽  
Palladium Catalyzed ◽  
Terminal Acetylenes ◽  
Alkyne Addition ◽  
Aryl Alkynes

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.

Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction

2021 ◽  
Vol 43 (1) ◽  
pp. 95-95
Author(s):  
Rifhat Bibi Rifhat Bibi ◽  
Muhammad Yaseen Muhammad Yaseen ◽  
Haseen Ahmad Haseen Ahmad ◽  
Ismat Ullah Khan Ismat Ullah Khan ◽  
Shaista Parveen Shaista Parveen ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Reaction ◽  
Terminal Alkynes ◽  
Vinyl Halides ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Alkyne Derivatives

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

ChemInform Abstract: A NEW SYNTHESIS OF ANTHRAMYCIN VIA PALLADIUM-CATALYZED CARBONYLATION

1982 ◽  
Vol 13 (46) ◽  
Author(s):  
M. ISHIKURA ◽  
M. MORI ◽  
M. TERASHIMA ◽  
Y. BAN
Keyword(s):  
New Synthesis ◽  
Palladium Catalyzed

Palladium-catalyzed oxidative homocoupling reaction of terminal acetylenes using trans-bidentatable 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene

2012 ◽  
Vol 39 (1) ◽  
pp. 359-370 ◽  
Author(s):  
Shingo Atobe ◽  
Motohiro Sonoda ◽  
Yuki Suzuki ◽  
Takuya Yamamoto ◽  
Haruna Masuno ◽  
...  
Keyword(s):  
Palladium Catalyzed ◽  
Terminal Acetylenes ◽  
Homocoupling Reaction ◽  
Oxidative Homocoupling
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