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

Mathan Sankaran; Kumarasamy Chandraprakash; Chokkalingam Uvarani; Kailasam Natesan Vennila; Devadasan Velmurugan; Palathurai Subramaniam Mohan

doi:10.1055/s-0032-1317488

Synlett, Table of Contents

Synlett 2012; 23(19): 2858-2864
DOI: 10.1055/s-0032-1317488

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

Mathan Sankaran

^aSchool of Chemical Sciences, Bharathiar University, Coimbatore 641046, India Fax: +91(422)2459845 Email: psmohan59@gmail.com

,

Kumarasamy Chandraprakash

^aSchool of Chemical Sciences, Bharathiar University, Coimbatore 641046, India Fax: +91(422)2459845 Email: psmohan59@gmail.com

,

Chokkalingam Uvarani

^aSchool of Chemical Sciences, Bharathiar University, Coimbatore 641046, India Fax: +91(422)2459845 Email: psmohan59@gmail.com

,

Kailasam Natesan Vennila

^bCentre for Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600025, India

,

Devadasan Velmurugan

^bCentre for Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600025, India

,

Palathurai Subramaniam Mohan*

^aSchool of Chemical Sciences, Bharathiar University, Coimbatore 641046, India Fax: +91(422)2459845 Email: psmohan59@gmail.com

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Abstract

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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

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References

References and Notes

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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: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].

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