The Scientific World Journal

Research Article

Zinc Oxide Nanoparticles Catalyzed Condensation Reaction of Isocoumarins and 1,7-Heptadiamine in the Formation of Bis-Isoquinolinones

Table 4

Physical data.


Va	White solid, mp 121–123°C, IR cm⁻¹ 1647 (C=O), 1336 (C–N), ¹H NMR (400 MHz, CDCl₃) 0.96 (m, 6H), 1.46 (m, 4H), 3.86 (t, 4H, J = 8.0 Hz, N-CH₂), 6.38 (s, 2H), 7.37–7.63 (m, 16H), 8.44 (d, 2H, J = 4.0 Hz) ppm. ¹³C NMR (100 MHz, CDCl₃) 26.55, 28.32, 28.61, 45.55 (symmetrical aliphatic carbons), 107.84, 125.34, 125.83, 126.63, 128.01, 128.81, 128.98, 129.14, 132.32, 136.21, 136.39, 143.75, 162.85 (symmetrical carbonyl carbons) ppm, HRMS [EI, M+] calcd for C₃₇H₃₄N₂O₂ m/z 538.2620, found 537.8527.

Vb	Off white solid, mp 110–112°C, IR cm⁻¹ 1647 (C=O), 1339 (C–N), ¹H NMR (400 MHz, CDCl₃) 0.88 (m, 6H), 1.25 (s, 6H), 1.45 (m, 4H), 3.85 (t, 4H, J = 4.0 Hz, N-CH₂), 6.35 (s, 2H), 7.26–7.47 (m, 14H), 8.41 (d, 2H, J = 8.0 Hz) ppm; ¹³C NMR (100 MHz, CDCl₃) 26.62, 28.40, 28.70, 29.90, 45.58 (symmetrical aliphatic carbons), 107.80, 125.49, 125.83, 126.65, 128.21, 128.57, 129.04, 129.20, 132.31, 135.13, 136.45, 143.79, 162.77 (symmetrical carbonyl carbons) ppm, HRMS [EI, M+] calcd for C₃₉H₃₈N₂O₂ m/z 566.2933, found 565.7487.

Vc	White solid, mp 117–119°C, IR cm⁻¹ 1646 (C=O), 1336 (C–N), 694 (C–F), ¹H NMR (500 MHz, CDCl₃) 1.02 (m, 6H), 1.48 (m, 4H),), 3.88 (t, 4H, J = 7.5 Hz, N-CH₂), 6.37 (s, 2H), 7.28–7.66 (m, 14H), 8.44 (d, 2H, J = 8.0 Hz) ppm. ¹³C NMR (125 MHz, CDCl₃) 26.41, 28.39, 28.62, 45.45 (symmetrical aliphatic carbons), 107.95, 123.21, 125.35, 125.77, 126.80, 127.99, 130.68, 131.69, 132.33, 135.13, 136.07, 142.37, 162.67 (symmetrical carbonyl carbons) ppm, HRMS [EI, M+] calcd for C₃₇H₃₂F₂N₂O₂ m/z 574.659, found 574.5888.

Vd	Pale yellow solid, mp 135–138°C, IR cm⁻¹ 1646 (C=O), 1337 (C–N), 687 (C–Cl), ¹H NMR (400 MHz, CDCl₃) 1.03 (m, 6H), 1.45 (m, 4H), 3.85 (t, 4H, J = 7.6 Hz, N-CH₂), 6.35 (s, 2H), 7.26–7.64 (m, 14H), 8.41 (d, 2H, J = 0.4 Hz) ppm. ¹³C NMR (100 MHz, CDCl₃) 26.41, 28.37, 28.60, 45.55 (symmetrical aliphatic carbons), 108.06, 125.29, 125.77, 126.80, 127.96, 128.72, 130.40, 132.34, 134.61, 135.03, 136.07, 142.31, 162.70 (symmetrical carbonyl carbons) ppm, HRMS [EI, M+] calcd for C₃₇H₃₂Cl₂N₂O₂ m/z 606.1841, found 606.8743.

Ve	White solid, mp 125–127°C, IR cm⁻¹ 1677 (C=O), 1321 (C–N), 696 (C–Br), ¹H NMR (500 MHz, CDCl₃) 1.02 (m, 6H), 1.48 (m, 4H), 3.88 (t, 4H, J = 7.5 Hz, N-CH₂), 6.38 (s, 2H), 7.28–7.66 (m, 14H), 8.44 (d, 2H, J = 8.0 Hz) ppm. ¹³C NMR (125 MHz, CDCl₃) 26.41, 28.38, 28.62, 45.46 (symmetrical aliphatic carbons), 107.98, 123.21, 125.33, 125.78, 126.81, 127.99, 130.68, 131.69, 132.34, 135.12, 136.07, 142.36, 162.68 (symmetrical carbonyl carbons) ppm, HRMS [EI, M+] calcd for C₃₇H₃₂Br₂N₂O₂ m/z 696.4702, found 696.3511.