Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids
Abstract
:1. Introduction
2. Results and Discussion
3/4 | 4-R | 4-X | % Yield 2 | % Yield 3 | % Yield 4 |
a | 4-H | 4-H | 24 ( 2a) | 12 | 57 |
b | 4-F | 4-H | 24 ( 2a) | 16 | 65 |
c | 4-Cl | 4-H | 24 ( 2a) | 10 | 54 |
d | 4-OMe | 4-H | 24 ( 2a) | 11 | 66 |
e | 4-H | 4-F | 20 ( 2b) | - | 65 |
f | 4-F | 4-F | 20 ( 2b) | - | 66 |
g | 4-Cl | 4-F | 20 ( 2b) | - | 56 |
h | 4-OMe | 4-F | 20 ( 2b) | - | 64 |
i | 4-H | 4-MeO | 17 ( 2c) | - | 63 |
j | 4-F | 4-MeO | 17 ( 2c) | 57 | |
k | 4-Cl | 4-MeO | 17 ( 2c) | - | 60 |
l | 4-OMe | 4-MeO | 17 ( 2c) | 9 | 68 |
3. Experimental
3.1. General
3.2. Typical Procedure for the PdCl2(PPh3)2-PCy3 Catalyzed Cross-Coupling Reactions of 1 with ArB(OH)2
3.2.1. Biphenyl (2a), 4-Azido-2,3-diphenylquinoline (3a) and 4-Amino-2,3-diphenylquinoline (4a)
3.2.2. Biphenyl (2a), 4-Azido-2-(4-fluorophenyl)-3-phenylquinoline (3b) and 4-Amino-2-(4-fluoro-phenyl)-3-phenylquinoline (4b)
3.2.3. Biphenyl (2a), 4-Azido-2-(4-chlorophenyl)-3-phenylquinoline (3c) and 4-Amino-2-(4-chloro-phenyl)-3-phenylquinoline (4c)
3.2.5. 4,4'-Difluoro-1,1'-biphenyl (2b) and 4-Amino-3-(4-fluorophenyl)-2-(phenyl)quinoline (4e)
3.2.6. 1-Fluoro-4-(4-fluorophenyl)benzene (2b) and 4-Amino-2,3-bis(4-fluorophenyl)quinoline (4f)
3.2.7. 1-Fluoro-4-(4-fluorophenyl)benzene (2b) and 4-Amino-2-(4-chlorophenyl)-3-(4-fluorophenyl)quinoline (4g)
3.2.8. 1-Fluoro-4-(4-fluorophenyl)benzene (2b) and 4-Amino-3-(4-fluorophenyl)-2-(4-methoxyphenyl)quinoline (4h)
3.2.9. 1-Methoxy-4-(4-methoxyphenyl)benzene (2c) and 4-Amino-3-(4-methoxyphenyl)-2-phenylquinoline (4i)
3.2.10. 1-Methoxy-4-(4-methoxyphenyl)benzene (2c) and 4-Amino-2-(4-fluorophenyl)-3-(4-methoxyphenyl)-quinoline (4j)
3.2.11. 1-Methoxy-4-(4-methoxyphenyl)benzene (2c) and 4-Amino-2-(4-chlorophenyl)-3-(4-methoxyphenyl)-quinoline (4k)
3.2.12. 1-Methoxy-4-(4-methoxyphenyl)benzene (2c), 4-Azido-2,3-bis(4-methoxyphenyl)quinoline (3l) and 4-Amino-2,3-bis(4-methoxyphenyl)quinoline (4l)
3.3. Typical Procedure for the Pd(OAc)2-Catalyzed Cross-Coupling Reactions of 1c,d with PhB(OH)2
3.3.1. Biphenyl (2a), 4-Azido-2-(4'-chlorophenyl)-3-phenylquinoline (3c) and 4-Amino-2-(4'-chloro-phenyl)quinoline (4c)
3.3.2. Biphenyl (2a), 4-Azido-2-(4'-methoxyphenyl)-3-phenylquinoline (3d) and 4-Amino-2-(4'-methoxyphenyl)quinoline (4d)
4. Conclusions
Acknowledgements
Conflict of Interest
References and Notes
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Mphahlele, M.J.; Mphahlele, M.M. Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids. Molecules 2011, 16, 8958-8972. https://doi.org/10.3390/molecules16118958
Mphahlele MJ, Mphahlele MM. Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids. Molecules. 2011; 16(11):8958-8972. https://doi.org/10.3390/molecules16118958
Chicago/Turabian StyleMphahlele, Malose Jack, and Mamasegare Mabel Mphahlele. 2011. "Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids" Molecules 16, no. 11: 8958-8972. https://doi.org/10.3390/molecules16118958