One-Pot Synthesis of 2,3,4-Triarylquinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-chloro-3-iodoquinolines with Arylboronic Acids
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. General
3.2. Typical procedure for the one-pot synthesis of 2,3,4-triarylquinolines 2
3.3. Synthesis of 2-aryl-4-chloro-3-(4-fluorophenyl)quinolines 2e-h. typical procedure
3.4. Reaction of 2e-h with aniline. typical procedure
3.5. Hydrolysis of 4 with acetic acid: typical procedure
4. Crystal Structure Solution and Refinement
5. Conclusions
Acknowledgements
References and Notes
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Sample Availability: Samples of the compounds are available from the authors. |
Comp | 4-R | Ar | % Yield (3) |
---|---|---|---|
a b c d e f g h | H F Cl OMe H F Cl OMe | -C6H5 -C6H5 -C6H5 -C6H5 p-FC6H4- p-FC6H4- p-FC6H4- p-FC6H4- | 59 55 61 58 72 75 62 62 |
4-R | % Yield (2) | % Yield (4) |
---|---|---|
H F Cl OMe | 60 (e) 55 (f) 61 (g) 79 (h) | 53 (a) 52 (b) 69 (c) 61 (d) |
Comp | % 4-R | % Yield (5) |
---|---|---|
a b c d | H F Cl OMe | 70 70 65 65 |
Ring | Torsion angles/deg (molecule A) | Torsion angles/deg (molecule B) | ||
---|---|---|---|---|
2-Ar | N(1)-C(1)-C(22)-C(23) | 42.09° | N(2)-C(28)-C(49)-C(50) | 60.22° |
C(2)-C(1)-C(22)-C(27) | 45.80° | C(29)-C(28)-C(49)-C(54) | 60.07° | |
3-Ar | C(1)-C(2)-C(10)-C(11) | 68.03° | C(30)-C(29)-C(37)-C(42) | 68.93° |
C(3)-C(2)-C(10)-C(15) | 67.27° | C(28)-C(29)-C(37)-C(38) | 66.95° | |
4-Ar | C(2)-C(3)-C(16)-C(17) | 68.08° | C(31)-C(30)-C(43)-C(48) | 74.75° |
C(4)-C(3)-C(16)-C(21) | 68.29° | C(29)-C(30)-C(43)-C(44) | 71.34° |
Empirical formula Formula weight Temperature Wavelength Crystal system Space group Unit cell dimensions Volume Z Density (calculated) Absorption coefficient F(000) Crystal size Theta range for data collection Index ranges Reflections collected Independent reflections Completeness to theta = 27.00° Absorption correction Max. and min. transmission Refinement method Data / restraints / parameters Goodness-of-fit on F2 Final R indices [I>2sigma(I)] R indices (all data) Largest diff. peak and hole | C56H38F6N2O 868.88 173(2) K 0.71073 Å Triclinic P-1 a = 10.2571(2) Å α = 103.2890(10)°. b = 13.2887(2) Å β = 99.4540(10)°. c = 16.7681(3) Å γ = 96.9390(10)°. 2164.00(7) Å3 2 1.333 Mg/m3 0.097 mm−1 900 0.44 × 0.37 × 0.37 mm3 1.27 to 27.00°. -13<=h<=13, -16<=k<=16, -21<=l<=21 40665 9440 [R(int) = 0.0484] 100.0 % None 0.9650 and 0.9586 Full-matrix least-squares on F2 9440 / 0 / 588 1.055 R1 = 0.0424, wR2 = 0.1057 R1 = 0.0640, wR2 = 0.1158 0.218 and -0.379 e.Å−3 |
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Mphahlele, M.J.; Mphahlele, M.M. One-Pot Synthesis of 2,3,4-Triarylquinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-chloro-3-iodoquinolines with Arylboronic Acids. Molecules 2010, 15, 7423-7437. https://doi.org/10.3390/molecules15107423
Mphahlele MJ, Mphahlele MM. One-Pot Synthesis of 2,3,4-Triarylquinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-chloro-3-iodoquinolines with Arylboronic Acids. Molecules. 2010; 15(10):7423-7437. https://doi.org/10.3390/molecules15107423
Chicago/Turabian StyleMphahlele, Malose Jack, and Mamasegare Mabel Mphahlele. 2010. "One-Pot Synthesis of 2,3,4-Triarylquinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-chloro-3-iodoquinolines with Arylboronic Acids" Molecules 15, no. 10: 7423-7437. https://doi.org/10.3390/molecules15107423