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Keywords = 2-aryl-2,3-dihydroquinolin-4(1H)-ones

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8 pages, 2367 KB  
Protocol
Synthesis Chalones and Their Isomerization into Flavanones and Azaflavanones
by Djenisa H. A. Rocha, Patrícia A. A. M. Vaz, Diana C. G. A. Pinto and Artur M. S. Silva
Methods Protoc. 2019, 2(3), 70; https://doi.org/10.3390/mps2030070 - 15 Aug 2019
Cited by 22 | Viewed by 4767
Abstract
Flavanones [2-aryl-2,3-dihydrochromen-4(1H)ones] and 2-aryl-2,3-dihydroquinolin-4(1H)-ones are valuable precursors in the synthesis of important pharmacological scaffolds, so efficient methodologies towards their synthesis are important in the medicinal chemistry context. Their synthesis also involves theoretical concepts such as aldol condensation, isomerization, and [...] Read more.
Flavanones [2-aryl-2,3-dihydrochromen-4(1H)ones] and 2-aryl-2,3-dihydroquinolin-4(1H)-ones are valuable precursors in the synthesis of important pharmacological scaffolds, so efficient methodologies towards their synthesis are important in the medicinal chemistry context. Their synthesis also involves theoretical concepts such as aldol condensation, isomerization, and catalysis that make it useful in an undergraduate organic chemistry laboratory. The use of both microwave irradiation as a source of energy to promote reactions and efficient catalysts are considered within green chemistry principles, mostly because the reaction yields are improved and reaction time decreased. In this paper, the efficiency of microwave irradiation use in the synthesis of chalcone derivatives and efficient catalyst systems to promote their isomerization into flavanones and 2-aryl-2,3-dihydroquinolin-4(1H)-ones is demonstrated. Full article
(This article belongs to the Collection Green Chemistry)
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19 pages, 1192 KB  
Article
Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines
by Tebogo Ankie Khoza, Marole Maria Maluleka, Neliswa Mama and Malose Jack Mphahlele
Molecules 2012, 17(12), 14186-14204; https://doi.org/10.3390/molecules171214186 - 30 Nov 2012
Cited by 10 | Viewed by 6229
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 [...] Read more.
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. Full article
(This article belongs to the Section Organic Chemistry)
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