Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones
Abstract
:1. Instruction
2. Results and Discussion
3. Experimental
3.1. Material and Methods
3.2. Starting Materials
3.2.1. Reaction of 1a–f with 2,3-Dichloropyrazine (2)
3.2.2. 5,12-Dihydropyrazino[2,3-c:5,6-c′]difuro[2,3-c:4,5-c′]diquinoline-6,14(5H,12H)-Dione (3a)
3.2.3. 2,10-Dichloro-5,12-Dihydropyrazino[2,3-c:5,6-c′]difuro[2,3-c:4,5-c′]-Diquinoline-6,14(5H,12H)-Dione (3b)
3.2.4. 3,11-Dichloro-5,12-Dihydropyrazino[2,3-c:5,6-c′]difuro[2,3-c:4,5-c′]diquinoline-6,14(5H,12H)-Dione (3c)
3.2.5. 2,10-Dibromo-5,12-Dihydropyrazino[2,3-c:5,6-c′]difuro[2,3-c:4,5-c′]diquinoline-6,14(5H,12H)-Dione (3d)
3.2.6. 5,12-Dihydro-3,11-Dimethylpyrazino[2,3-c:5,6-c′]difuro[2,3-c:4,5-c′]diquinoline-6,14(5H,12H)-Dione (3e)
3.2.7. 5,12-Dihydro-2,10-Dimethylpyrazino[2,3-c:5,6-c′]difuro[2,3-c:4,5-c′]diquinoline-6,14(5H,12H)-Dione (3f)
3.3. Reaction of 1a–f with (E)-1,2-Dibenzoylethene (4)
3.3.1. 2-(4-Hydroxy-2-oxo-1,2-Dihydroquinolin-3-yl)-1,4-Diphenylbutane-1,4-Dione (6a)
3.3.2. 2-(6-Chloro-4-Hydroxy-2-oxo-1,2-Dihydroquinolin-3-yl)-1,4-Diphenylbutane-1,4-Dione (6b)
3.3.3. 2-(7-Chloro-4-Hydroxy-2-oxo-1,2-Dihydroquinolin-3-yl)-1,4-Diphenylbutane-1,4-Dione (6c)
3.3.4. 2-(6-Bromo-4-Hydroxy-2-oxo-1,2-Dihydroquinolin-3-yl)-1,4-Diphenylbutane-1,4-Dione (6d)
3.3.5. 2-(4-Hydroxy-7-Methyl-2-oxo-1,2-Dihydroquinolin-3-yl)-1,4-Diphenylbutane-1,4-Dione (6e)
3.3.6. 2-(4-Hydroxy-6-Methyl-2-oxo-1,2-Dihydroquinolin-3-yl)-1,4-Diphenylbutane-1,4-Dione (6f)
3.3.7. 4-(Benzo[d]oxazol-2-yl)-3-Hydroxy-1H-Benzo[4,5]oxazolo[3,2-a]pyridine-1-one (11)
3.3.8. (4-(Benzo[d]oxazol-2-yl)-3-Hydroxy-1-oxo-1H-Benzo[4,5]oxazolo[3,2-a]pyridin-2-yl)-1,4-Diphenylbutane-1,4-Dione (12)
3.4. Crystal Structure Determinations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
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Aly, A.A.; Hassan, A.A.; Mohamed, N.K.; El-Haleem, L.E.A.; Bräse, S.; Polamo, M.; Nieger, M.; Brown, A.B. Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones. Molecules 2019, 24, 3782. https://doi.org/10.3390/molecules24203782
Aly AA, Hassan AA, Mohamed NK, El-Haleem LEA, Bräse S, Polamo M, Nieger M, Brown AB. Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones. Molecules. 2019; 24(20):3782. https://doi.org/10.3390/molecules24203782
Chicago/Turabian StyleAly, Ashraf A., Alaa A. Hassan, Nasr K. Mohamed, Lamiaa E. Abd El-Haleem, Stefan Bräse, Mika Polamo, Martin Nieger, and Alan B. Brown. 2019. "Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones" Molecules 24, no. 20: 3782. https://doi.org/10.3390/molecules24203782