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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2012-11, Vol.17 (12), p.14186-14204
Main Authors: Khoza, Tebogo Ankie, Maluleka, Marole Maria, Mama, Neliswa, Mphahlele, Malose Jack
Format: Article
Language:English
Subjects:
1-(2-amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones
2-aryl-6,8-bis(2-aryl-ethenyl)-4-methoxyquinolines
2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones
2-aryl-6,8-dibromo-4-methoxyquinolines
2-aryl-6,8-dibromoquinolin-4(1H)-ones
Absorption
Acids
Fluorescence
Iodine
Iodine - chemistry
MicroRNAs
Molecular Structure
Oxidation-Reduction
photophysical properties
Quinolines - chemical synthesis
Quinolines - chemistry
Suzuki-Miyaura cross-coupling
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules171214186