Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines
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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2012-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/17/12/14186 |
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| author | Tebogo Ankie Khoza Marole Maria Maluleka Neliswa Mama Malose Jack Mphahlele |
| author_facet | Tebogo Ankie Khoza Marole Maria Maluleka Neliswa Mama Malose Jack Mphahlele |
| author_sort | Tebogo Ankie Khoza |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T01:48:48Z |
| format | Article |
| id | doaj.art-d86cf299f96c4277b555aea7a1a1189f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T01:48:48Z |
| publishDate | 2012-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d86cf299f96c4277b555aea7a1a1189f2022-12-22T03:53:00ZengMDPI AGMolecules1420-30492012-11-011712141861420410.3390/molecules171214186Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolinesTebogo Ankie KhozaMarole Maria MalulekaNeliswa MamaMalose Jack MphahleleIodine-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.http://www.mdpi.com/1420-3049/17/12/141861-(2-amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones2-aryl-6,8-dibromoquinolin-4(1H)-ones2-aryl-6,8-dibromo-4-methoxyquinolinesSuzuki-Miyaura cross-coupling2-aryl-6,8-bis(2-aryl-ethenyl)-4-methoxyquinolinesphotophysical properties |
| spellingShingle | Tebogo Ankie Khoza Marole Maria Maluleka Neliswa Mama Malose Jack Mphahlele Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines Molecules 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 |
| title | Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines |
| title_full | Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines |
| title_fullStr | Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines |
| title_full_unstemmed | Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines |
| title_short | Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines |
| title_sort | synthesis and photophysical properties of 2 aryl 6 8 bis arylethenyl 4 methoxyquinolines |
| topic | 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 |
| url | http://www.mdpi.com/1420-3049/17/12/14186 |
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