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

Molecules

Tebogo Ankie Khoza¹  Marole Maria Maluleka¹  Neliswa Mama¹ 

[1] ¹Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa ²Department of Chemistry, Nelson Mandela Metropolitan University, P.O. Box 77000, Port Elizabeth 6031, South Africa

关键词: 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;   

DOI  :  10.3390/molecules171214186

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.