Synlett 2014; 25(15): 2176-2178
DOI: 10.1055/s-0034-1378518
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Pyridocarbazoles Analogues of Ellipticine

Ramu Meesala*, Mohammed Oday Ezzat, Mohd Nizam Mordi, Sharif Mahsufi Mansor
  • Centre For Drug Research, Universiti Sains Malaysia, Minden, 11800 USM, Penang, Malaysia   Fax: +6046568669   Email: cu_ram@yahoo.co.in
Further Information

Publication History

Received: 09 May 2014

Accepted after revision: 20 June 2014

Publication Date:
11 August 2014 (eFirst)

Abstract

Derivatives of pyrido[3,2-b]carbazole and pyrido[2,3-c]carbazole have been synthesized by the Vilsmeier–Haack reaction of N-(carbazol-3-yl)acetamides.

Supporting Information

 
  • References and Notes

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  • 17 General Procedure To a solution N-(6-ethoxy-9-ethyl-9H-carbazol-3-yl)acetamide (1 mmol) in POCl3 (10 mmol) at 0–5 °C with stirring dry DMF (2.5 mmol) was added dropwise, and the mixture was heated at 70 °C for 12 h. On completion of the reaction (TLC), the mixture was poured onto crushed ice, the mixture stirred for 15 min, and the resulting solid filtered, washed well with H2O and dried. The crude material was purified by column chromatography to separate the linear and angular products. 2-Chloro-9-ethoxy-6-ethyl-6H-pyrido[3,2-b]carbazole-3-carbaldehyde (2a) Mp 178–180. IR (KBR): 2921, 2844, 1683, 1576, 1471, 1286, 1169, 1084, 923 cm–1. 1H NMR (500 MHz, TMS, CDCl3): δ = 10.49 (1 H, s), 8.78 (1 H, s), 8.59 (1 H, s), 7.65–7.63 (2 H, m), 7.27 (1 H, d, J = 10.0 Hz), 7.21 (1 H, d, J = 2.0 Hz), 4.32 (2 H, q, J = 7.5 Hz), 4.12 (2 H, q, J = 7.0 Hz), 1.44 (3 H, t, J = 7.0 Hz), 1.40 (3 H, t, J = 10.0 Hz). 13C NMR (125 MHz, TMS, CDCl3): δ = 189.6, 153.4, 146.2, 143.0, 140.6, 139.6, 138.2, 131.2, 124.9, 124.8, 122.3, 118.9, 118.8, 109.4, 106.3, 104.8, 64.6, 38.1, 15.0, 13.4. GC–MS: m/z = 352.5. Anal. Calcd for C20H17ClN2O2: C, 68.09; H, 4.86; N, 7.94. Found: C, 68.23; H, 5.05; N, 7.85. 3-Chloro-10-ethoxy-7-ethyl-7H-pyrido[2,3-c]carbazole-2-carbaldehyde (3a) Mp 190–192. IR (KBR): 2935, 2850, 1673, 1585, 1460, 1283, 1175, 1087, 929 cm–1. 1H NMR (500 MHz, TMS, CDCl3): δ = 10.55 (1 H, s), 9.33 (1 H, s), 7.94 (1 H, d, J = 9.5 Hz), 7.87 (1 H, d, J = 9.5 Hz), 7.83 (1 H, d, J = 2.0 Hz), 7.41 (1 H, d, J = 9.0 Hz), 7.16–7.14 (1 H, m), 4.42 (2 H, q, J = 7.5 Hz), 4.18 (2 H, q, J = 7.0 Hz), 1.48 (3 H, t, J = 7.0 Hz), 1.42 (3 H, t, J = 7.0 Hz). 13C NMR (125 MHz, TMS, CDCl3): δ = 189.7, 154.2, 146.4, 146.3, 137.5, 134.6, 134.0, 126.1, 125.8, 123.2, 123.0, 118.0, 115.9, 115.0, 110.5, 105.8, 64.7, 38.0, 15.1, 14.6. GC–MS: m/z = 352.5. Anal. Calcd for C20H17ClN2O2: C, 68.09; H, 4.86; N, 7.94. Found: C, 67.79; H, 4.78; N, 8.16.
  • 18 CCDC number of 2d is 1001381. Formula: C18H13Cl1N2O1, unit cell parameters: a = 12.360(3), b = 13.961(3), c = 8.999(2), α = 90°, β = 108.336(3)°, γ = 90°, space group P21/c.