A Convenient Method of Facilitating Aryl–Aryl Bond-Formation Reactions in the Synthesis of Biquinoline- and Quinoline-Bearing Chromene Derivatives

Abstract

A method to derive functionalized biquinoline- and quinoline-bearing chromene bicyclic systems through aryl–aryl bond formation in a one-pot synthesis is described. The X-ray structure analysis provides insight into the mode of orientation of the molecules and opens the way to the synthesis of various hybrid molecules by making use of suitable substituents at R¹, R², and R³.

Key words

one-pot synthesis - quinoline - chromene - sulfuric acid - p-toluenesulphonic acid

• References and Notes

• 1a Zhang JY. P, Zhang KY. H, Jiang S, Ye L, Yang G, Wang Y. J. Solid State Chem. 2006; 179: 438
• 1b Zhou J, Yan S, Zheng X, Lic L, Jin L. Cryst. Eng. Commun. 2009; 11: 2640
• 1c Pucci D, Crispini A, Ghedini M, Szerb EI, Deda ML. Dalton Trans. 2011; 4614
• 2 Depero LE, Curri ML. Curr. Opin. Solid State Mater. Sci. 2004; 8: 103
• 3 Ruben M, Rojo J, Salguero FJ. R, Uppadine LH, Lehn JM. Angew. Chem. Int. Ed. 2004; 43: 3644
• 4 Maspoch D, Ruiz-Molinaa D, Veciana J. Chem. Soc. Rev. 2007; 36: 770
• 5 Yan Y, Huang J. Coord. Chem. Rev. 2010; 254: 1072
• 6 Batten SR, Robson R. Angew. Chem. Int. Ed. 1998; 37: 1460 ; Angew. Chem. 1998, 110, 1559
• 7a Janiak C. Angew. Chem. Int. Ed. Engl. 1997; 36: 1431 ; Angew. Chem. 1997, 109, 1499
• 7b Yaghi OM, Li H, Davis C, Richardson D, Groy TL. Acc. Chem. Res. 1998; 31: 474
• 8 Lehn JM. Supramolecular Chemistry . Wiley-VCH; Weinheim: 1995
• 9 MacGillivray LR, Groeneman RH, Atwood JL. J. Am. Chem. Soc. 1998; 120: 2676
• 10 Horcajada P, Chalati T, Serre C, Gillet B, Sebrie C, Baati T, Couvreur P, Gref R. Nature Materials 2010; 9: 172
• 11 Batten SR, Robson R. Angew. Chem. Int. Ed. 1998; 37: 1460 ; Angew. Chem. 1998, 110, 1559
• 12a Janiak C. Angew. Chem., Int. Ed. Engl. 1997; 36: 1431 ; Angew. Chem. 1997, 109: 1499
• 12b Yaghi OM, Li H, Davis C, Richardson D, Groy TL. Acc. Chem. Res. 1998; 31: 474
• 13 Hunter CA. Angew. Chem., Int. Ed. Engl. 1995; 34: 1079 ; Angew. Chem. 1995, 107, 1181
• 14 Brunet P, Simard M, Wuest JD. J. Am. Chem. Soc. 1997; 119: 2737
• 15 Raynes K, Foley M, Tilley L, Deady LW. Biochem. Pharmacol. 1996; 52: 551
• 16 Ali BasemF, Al-Souod K, Al-Ja’ar N, Nasser A, Zaghal MH, Judeh Z, Al-Far R, Al-Refai M, Al-Obaidi KH. J. Coord. Chem. 2006; 59: 229
• 17 Wrasidlo W, Norris SO, Wolfe JF, Katto T, Stille JK. Macromolecules 1976; 9: 512
• 18 Wrasidlo W, Stille JK. Macromolecules 1976; 9: 505
• 19 Ichikawa J, Mori T, Miyazaki H, Wada Y. Synlett 2004; 1219
• 20 Saavedra LA, Vallejos CG, Kouznetsov VV, Gutierrez CM, Meléndez Gómez CM, Leonor Y, Méndez V, Jaimes JH. B. Synthesis 2010; 593
• 21 Viau L, Senechal K, Maury O, Guegan JP, Dupau P, Toupet L, Bozec HL. Synthesis 2003; 577
• 22 Janiak C, Deblon S, Uehlin L. Synthesis 1999; 959
• 23 Aksenov AV, Goncharov VI. Chem. Heterocycl. Compd. (Engl. Transl.) 2008; 44: 12
• 24 Hu YZ, Zhang G, Thummel RP. Org. Lett. 2003; 5: 2251
• 25 Pucci D, Crispini A, Ghedini M, Szerb EI, Deda ML. Dalton Trans. 2011; 4614
• 26a Oparine MP. Ber. Dtsch. Chem. Ges. B 1931; 64: 569
• 26b Bak BJ. J. Org. Chem. 1956; 21: 797
• 27 Nakano S. J. Pharm. Soc. Jpn. 1959; 79: 310
• 28 Lekhok KC, Bhuyan D, Prajapati D, Boruah RC. Mol. Diversity 2010; 14: 841
• 29 Jian FZ, Xiao JS, Feng WL, Meng L, Lu L. Z. Res. Chem. Intermed. DOI: 10.1007/s11164-012-0696-5
• 30 6,6′-Dinitro-4,4′-diphenyl-2,3′-biquinolin-2′(1′H)-one (3g): To a stirred suspension of 2-amino-5-nitrobenzophenone (2d; 1 mmol) in acetic acid (20 mL), appropriate 3-acetyl-6-nitro-4-phenylquinolin-2(1H)-one (1d; 1 mmol) was added, followed by the addition of a catalytic amount of H₂SO₄ (0.5 equiv). The reaction mixture was heated to reflux for 3–5 h and the course of the reaction was monitored by TLC. After cooling to r.t., the mixture was poured into crushed ice (500 g) and the resulting residue was filtered to afford the desired product, which was purified by silica gel column chromatography (hexane–EtOAc, 7:3 v/v) to afford the target compound (72%) as a pale-yellow solid. Mp 254–258 °C. IR (KBr): 3311.18, 2865.7, 1822.4, 1653.66, 1532.17, 1334.5, 1258.32, 1069.33, 897.70, 703.89 cm^–1. ¹H NMR (400 MHz, DMSO-d ₆): δ = 12.88 (s, 1 H, Q-NH), 8.63 (d, J = 2.5 Hz, 1 H, ArH), 8.42–8.45 (m, 2 H, ArH), 8.11 (d, J = 9.0 Hz, 1 H, ArH), 7.98 (d, J = 2.5 Hz, 1 H, ArH), 7.61–7.65 (m, 5 H, ArH), 7.46 (dd, J = 1.5, 8 Hz, 2 H, ArH), 7.33–7.36 (m, 5 H, ArH). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 161.36, 158.77, 150.02, 149.08, 145.87, 143.61, 142.16, 136.31, 134.45, 132.98, 131.69, 129.88, 129.58, 129.04, 128.77, 125.86, 123.93, 113.33, 119.71, 117.21. MS: m/z = 514 [M + H]. Anal. Calcd for C₃₀H₁₈N₄O₅: C, 70.03; H, 3.53; N, 10.89. Found: C, 69.98; H, 3.55; N, 10.92%.
• 31 Xuegang C, Dongfang Q, Liang M, Xanxiang C, Yanhou G, Zhiyuan X, Lixiang W. Transition Met. Chem. 2006; 31: 639
• 32 7-Methoxy-3-(4-phenylquinolin-2-yl)-2H-chromen-2-one (5g): To a stirred suspension of 2-aminobenzophenone (2a; 1 mmol) in acetic acid (20 mL), appropriate 3-acetyl-7-methoxy-2H-chromen-2-one (4b; 1 mmol) was added, followed by the addition of a catalytic amount of H₂SO₄ (0.5 equiv). The reaction mixture was heated to reflux for 3–5 h, then the course of the reaction was monitored by TLC. After cooling to r.t., the mixture was poured into crushed ice (500 g); the resulting residue was filtered to afford the desired product, which was purified by silica gel column chromatography (hexane–EtOAc, 8:2 v/v) to afford the target compound (82%) as a pale-green solid. Mp 216–220 °C. IR (KBr): 3059.51, 1718.26, 617.02, 1583.27, 1502.28, 1358.6, 1237.11, 1187.94, 1021.12, 834.06, 703.89 cm^–1; ¹H NMR (400 MHz, DMSO-d ₆): δ = 8.99 (s, 1 H, C4-H), 8.40 (s, 1 H, C4–H), 8.22 (d, J = 8.50 Hz, 1 H, ArH), 7.97 (d, J = 8.50 Hz, 1 H, ArH), 7.76 (t, J = 8.00 Hz, 1 H, ArH), 7.51–7.60 (m, 6 H, ArH), 6.95 (d, J = 2.00 Hz, 1 H, ArH), 6.93 (dd, J = 2.50, 10.00 Hz, 1 H, ArH). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 163.46, 160.80, 156.23, 152.16, 148.69, 148.52, 143.82, 138.22, 130.08, 129.76, 129.74, 129.48, 128.53, 128.38, 126.65, 126.26, 125.79, 122.57, 121.81, 113.41, 113.19, 100.31, 55.86; MS: m/z = 379 [M + H]. Anal. Calcd for C₂₅H₁₇NO₃: C, 79.14; H, 4.52; N, 3.69. Found: C, 7.19; H, 4.49; N, 3.71%.
• 33 Cif files for 5f and 5g have been deposited with the Cambridge Crystallographic Data Centre as CCDC-895741 (5f) and 890933 (5g). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK. [Fax: [phone] or e-mail: [e-mail]].