Synthesis and Single Crystal X-Ray Studies of 3-(3,5-Bis (trifluoromethyl) phenyl) Quinoline and 3-(4-Fluoro-3-methylphenyl) Quinoline
Malik Aman Ullah;Muhammad Adeel;Muhammad Nawaz Tahir;Irfan Ullah;Muhammad Raza Shah
a (Department of Chemistry, Gomal University, Dera Ismail Khan, KPK, Pakistan)
b (Department of Physics, University of Sargodha, Sargodha, Punjab, Pakistan)
c (ICCBS, HEJ Research Institute of Chemistry, University of Karachi, Karachi-75270, Sindh, Pakistan)
Synthesis and Single Crystal X-Ray Studies of 3-(3,5-Bis (trifluoromethyl) phenyl) Quinoline and 3-(4-Fluoro-3-methylphenyl) Quinoline
Malik Aman Ullah;Muhammad Adeel;Muhammad Nawaz Tahir;Irfan Ullah;Muhammad Raza Shah
a (Department of Chemistry, Gomal University, Dera Ismail Khan, KPK, Pakistan)
b (Department of Physics, University of Sargodha, Sargodha, Punjab, Pakistan)
c (ICCBS, HEJ Research Institute of Chemistry, University of Karachi, Karachi-75270, Sindh, Pakistan)
摘要The title compounds 3-(3,5-bis(trifluoromethyl)phenyl)quinoline (1) and 3-(4- fluoro-3-methylphenyl)quinoline (2) were synthesized through Suzuki-Miyaura Cross coupling reaction of 3-bromoquinoloine with aryl boronic acids. The title compounds were characterized by single-crystal X-ray diffraction, 1H NMR, 13C NMR, EI-MS, elemental analysis and IR. The crystals of 3-(3,5-bis(trifluoromethyl)phenyl)quinoline (C17H9F6N, Mr= 341.25) belongs to the monoclinic system, space group P21n, α = 12.3072(13), b = 4.9378(6), c = 24.493(2) Å, V = 1473.1(3) Å3, Z = 4, Dc= 1.539 Mg m−3, λ = 0.71073 Å, μ = 0.144 mm−1, F(000) = 688, the final R = 0.0715 and wR = 0.1873 for 1875 observed reflections with I > 2σ(I) and the crystal of 3-(4-fluoro-3- methylphenyl)quinoline (C16H12FN, Mr= 237.27) belongs to the orthorhombic system, space group Pca21, α = 23.794(2), b = 3.9094(3), c = 25.669(2) Å, V = 2387.7(4) Å3, Z = 8, Dc = 1.320 Mg m−3, λ = 0.71073 Å, μ = 0.088 mm−1, F(000) = 992, the final R = 0.0534 and wR = 0.1188 for 2270 observed reflections with I > 2σ(I).
Abstract：The title compounds 3-(3,5-bis(trifluoromethyl)phenyl)quinoline (1) and 3-(4- fluoro-3-methylphenyl)quinoline (2) were synthesized through Suzuki-Miyaura Cross coupling reaction of 3-bromoquinoloine with aryl boronic acids. The title compounds were characterized by single-crystal X-ray diffraction, 1H NMR, 13C NMR, EI-MS, elemental analysis and IR. The crystals of 3-(3,5-bis(trifluoromethyl)phenyl)quinoline (C17H9F6N, Mr= 341.25) belongs to the monoclinic system, space group P21n, α = 12.3072(13), b = 4.9378(6), c = 24.493(2) Å, V = 1473.1(3) Å3, Z = 4, Dc= 1.539 Mg m−3, λ = 0.71073 Å, μ = 0.144 mm−1, F(000) = 688, the final R = 0.0715 and wR = 0.1873 for 1875 observed reflections with I > 2σ(I) and the crystal of 3-(4-fluoro-3- methylphenyl)quinoline (C16H12FN, Mr= 237.27) belongs to the orthorhombic system, space group Pca21, α = 23.794(2), b = 3.9094(3), c = 25.669(2) Å, V = 2387.7(4) Å3, Z = 8, Dc = 1.320 Mg m−3, λ = 0.71073 Å, μ = 0.088 mm−1, F(000) = 992, the final R = 0.0534 and wR = 0.1188 for 2270 observed reflections with I > 2σ(I).
基金资助:This research was supported by HEC, Pakistan and WUS, Germany
通讯作者:
Muhammad Adeel: adeel.gu@yahoo.com
E-mail: adeel.gu@yahoo.com
作者简介: Muhammad Adeel: adeel.gu@yahoo.com
引用本文:
Malik Aman Ullah;Muhammad Adeel;Muhammad Nawaz Tahir;Irfan Ullah;Muhammad Raza S. Synthesis and Single Crystal X-Ray Studies of 3-(3,5-Bis (trifluoromethyl) phenyl) Quinoline and 3-(4-Fluoro-3-methylphenyl) Quinoline[J]. 结构化学, 2014, 33(1): 90-96.
Malik Aman Ullah;Muhammad Adeel;Muhammad Nawaz Tahir;Irfan Ullah;Muhammad Raza Shah. Synthesis and Single Crystal X-Ray Studies of 3-(3,5-Bis (trifluoromethyl) phenyl) Quinoline and 3-(4-Fluoro-3-methylphenyl) Quinoline. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2014, 33(1): 90-96.
(1)Woodward, R. R. The Chemistry of the Cinchona Alkaloids. Academic Press: New York ,Vol. 3, Ch. 16 1953.
(2)Stork, G.; Niu, D.; Fujimoto, R. A.; Koft, E. R.; Balkevec, J. M.; Tata, J. R.; Dake, G. R. The first stereoselective total synthesis of quinine. J. Am. Chem. Soc. 2001, 123, 3239–3242.
(4)Cappelli, A.; Giuliani, G.; Gallelli, A.; Valenti, S.; Anzini, M.; Mennuni, L.; Makovec, F.; Cupello, A. Structure-affinity relationship studies on arylpiperazine derivatives related to quipazine as serotonin transporter ligands. Molecular basis of the selectivity SERT/5HT3 receptor, Bioorg. Med. Chem.2005, 13, 3455–3460.
(5)Matsumiya, H.; Hoshino, H.; Yotsuyanagi, T. A novel fluorescence reagent, 10-hydroxybenzo[h]quinoline-7-sulfonate, for selective determination of beryllium(II) ion at pg cm−3 levels. Analyst2001, 126, 2082–2086.
(6)Prema, D.; Wiznycia, A. V.; Scott, B. M. T.; Hilborn, J.; Desper, J.; Levy, C. J. Dinuclear zinc(II) complexes of symmetric Schiff-base ligands with extended quinoline sidearms. J. Chem. Soc. ,Dalton Trans.2007, 4788–4796.
(7)Lutz, R. E.; Bailey, P. S.; Clark, M. T.; Codington, J. F.; Dinet, A. J.; Freek, J. A.; Harnest, G. H.; Leake, N. H.; Martin, T. A.; Rowlett, R. J.; Salsbury, J. M.; Shearer, N. H.; Smith, J. D.; Wilson, J. W. Antimalarials α-alkyl and dialkylaminomethyl-2-phenyl-4-quinolinemethanols. J. Am. Chem. Soc. 1946, 68, 1813–1831.
(9)Fang, K. C.; Chen, Y. L.; Sheu, J. Y.; Wang, T. C.; Tzeng, C. C. Synthesis, antibacterial, and cytotoxic evaluation of certain 7-substituted norfloxacin derivatives. J. Med. Chem. 2000, 43, 3809–3812.
(10)Chevalier, J.; Atifi, S.; Eyraud, A.; Mahamoud, A.; Barbe, J.; Pages, J. M. New pyridoquinoline derivatives as potential inhibitors of the fluoroquinolone efflux pump in resistant enterobacter aerogenes strains. J. Med. Chem. 2001, 44, 4023–4026.
(11)Majerz-Maniecka, K.; Oleksyn, B.; Musiol, R.; Podeszwa, B.; Polanski, J. Joint Meeting on Medicinal Chemistry. Vienna, Austria 2005, June 20–23. Sci Pharm 73 (Suppl. 1):194.
(13)Dassonneville, L.; Lansiaux, A.; Wattelet, A.; Wattez, N.; Mahieu, C.; Van Miert, S.; Pieters, L.; Bailly, C. Cytotoxicity and cell cycle effects of the plant alkaloids cryptolepine and neocryptolepine: relation to drug-induced apoptosis. Eur. J. Pharmacol. 2000, 409, 9–18.
(14)Ablordeppey, S. Y.; Fan, P.; Li, S.; Clark, A. M.; Hufford, C. D. Substituted indoloquinolines as new antifungal agents. Bioorg. Med. Chem. 2002, 10, 1337–1346.
(15)Khan, M. T. H. Quinoline analogs as antiangiogenic agents and telomerase inhibitors. In: Khan MTH, Gupta R (eds) Bioactive heterocycles. V. R. Springer-Verlag, Berlin. Top. Heterocycl. Chem. 2007, 11, 213–229.
(16)Jones, G. Comprehensive Heterocyclic Chemistry II, Vol 5. (Eds.: Katritzky, A. R; Rees, C. W.; Scriven, E. F. V.). Pergamon Press, Oxford 1996, 167–243.
2014, Vol. 33 
