Molecules 2012, 17(12), 14186-14204; doi:10.3390/molecules171214186
Article

Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines

Tebogo Ankie Khoza 1 , Marole Maria Maluleka 1 , Neliswa Mama 2  and Malose Jack Mphahlele 1,* email
1 Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa 2 Department of Chemistry, Nelson Mandela Metropolitan University, P.O. Box 77000, Port Elizabeth 6031, South Africa
* Author to whom correspondence should be addressed.
Received: 8 November 2012; in revised form: 20 November 2012 / Accepted: 23 November 2012 / Published: 30 November 2012
(This article belongs to the Section Organic Synthesis)
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Abstract: Iodine-methanol mediated oxidative-aromatization of 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones afforded the corresponding 2-aryl-6,8-dibromo-4-methoxy-quinolines in high yield and purity. The isomeric 1-(2-amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones reacted with iodine in methanol afford in a single pot operation the corresponding 2-aryl-6,8-dibromo-4-methoxyquinoline (major) and 2-aryl-6,8-dibromoquinolin-4(1H)-one (minor) products that were separated in sequence by column chromatography on silica gel. Suzuki-Miyaura cross-coupling of the 6,8-dibromo-4-methoxyquinoline derivatives with excess arylvinylboronic acids afforded the corresponding 2-aryl-6,8-bis(2-arylethenyl)-4-methoxyquinolines. The absorption and fluorescence properties of these compounds were also determined.
Keywords: 1-(2-amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones; 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones; 2-aryl-6,8-dibromoquinolin-4(1H)-ones; 2-aryl-6,8-dibromo-4-methoxyquinolines; Suzuki-Miyaura cross-coupling; 2-aryl-6,8-bis(2-aryl-ethenyl)-4-methoxyquinolines; photophysical properties

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MDPI and ACS Style

Khoza, T.A.; Maluleka, M.M.; Mama, N.; Mphahlele, M.J. Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines. Molecules 2012, 17, 14186-14204.

AMA Style

Khoza TA, Maluleka MM, Mama N, Mphahlele MJ. Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines. Molecules. 2012; 17(12):14186-14204.

Chicago/Turabian Style

Khoza, Tebogo A.; Maluleka, Marole M.; Mama, Neliswa; Mphahlele, Malose J. 2012. "Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines." Molecules 17, no. 12: 14186-14204.

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