Synlett, Inhaltsverzeichnis Synlett 2014; 25(15): 2176-2178DOI: 10.1055/s-0034-1378518 letter © Georg Thieme Verlag Stuttgart · New YorkSynthesis of Novel Pyridocarbazoles Analogues of Ellipticine Autor*innen Institutsangaben Ramu Meesala* Centre For Drug Research, Universiti Sains Malaysia, Minden, 11800 USM, Penang, Malaysia Fax: +6046568669 eMail: cu_ram@yahoo.co.in Mohammed Oday Ezzat Centre For Drug Research, Universiti Sains Malaysia, Minden, 11800 USM, Penang, Malaysia Fax: +6046568669 eMail: cu_ram@yahoo.co.in Mohd Nizam Mordi Centre For Drug Research, Universiti Sains Malaysia, Minden, 11800 USM, Penang, Malaysia Fax: +6046568669 eMail: cu_ram@yahoo.co.in Sharif Mahsufi Mansor Centre For Drug Research, Universiti Sains Malaysia, Minden, 11800 USM, Penang, Malaysia Fax: +6046568669 eMail: cu_ram@yahoo.co.in Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) 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. Key words Key wordspyrido[3,2-b]carbazoles - pyrido[2,3-c]carbazoles - N-(carbazol-3-yl)acetamides - Vilsmeier–Haack reagent Volltext Referenzen References and Notes 1 Goodwin S, Smith AF, Horning EC. J. Am. Chem. Soc. 1959; 81: 1903 2a Schmidt AW, Reddy KR, Knölker H.-J. Chem. Rev. 2012; 112: 3193 2b Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303 2c Kansal VK, Potier P. Tetrahedron 1986; 42: 2389 2d Sainsbury M. Synthesis 1977; 437 2e Barone R, Chanon M. Heterocycles 1981; 16: 1357 2f Hewlins MJ. E, Oliveira-Campos A.-M, Shannon PV. R. Synthesis 1984; 289 2g Gribble GW, Saulnier MG. Heterocycles 1985; 23: 1277 2h Suffness M, Cordell GA In The Alkaloids . Vol. 25. Brossi A. Academic Press; New York: 1985: 89 2i Suffness M, Cordell GA In The Alkaloids . Vol. 25. Brossi A. Academic Press; New York: 1985: 304 2j Pindur U. Pharm. Unserer Zeit 1987; 47 3a Gribble GW In Advances in Heterocyclic Natural Product Synthesis . Vol. 1. Pearson WH. JAI Press; Greenwich, CT: 1990: 43 3b Gribble GW In The Alkaloids . Vol. 39. Brossi A. Academic Press; New York: 1990: 239 3c Gribble GW. Synlett 1991; 289 3d Pindur U, Haber M, Sattler K. Pharm. Unserer Zeit 1992; 21 3e Potier P. Chem. Soc. Rev. 1992; 21: 113 3f Álvarez M, Joule JA In The Alkaloids . Vol. 57. Cordell GA. Academic Press; New York: 2001: 235 3g Knölker H.-J, Reddy KR In The Alkaloids . Vol. 65. Cordell GA. Academic Press; New York: 2008: 1 4a Chabane H, Lamazzi C, Thiéry V, Guillaumet G, Besson T. Tetrahedron Lett. 2002; 43: 2483 4b Grummitt AR, Harding MM, Anderberg PI, Rodger A. Eur. J. Org. Chem. 2003; 63 4c Saturnino C, Buonerba M, Boatto G, Pascale M, Moltedo O, Napoli LD, Montesarchio D, Lancelot J.-C, de Caprariis P. Chem. Pharm. Bull. 2003; 51: 971 4d Tran-Thi HA, Nguyen-Thi T, Michel S, Tillequin F, Koch M, Pfeiffer B, Pierré A, Trinh-Van-Dufat H. Chem. Pharm. Bull. 2004; 52: 540 5a Meesala R, Nagarajan R. Tetrahedron 2009; 65: 6050 5b Caruso A, Lancelot J.-C, El-Kashef H, Sinicropi MS, Legay R, Lesnard A, Rault S. Tetrahedron 2009; 65: 10400 5c Al-Trawneh SA, Zahra JA, Kamal MR, El-Abadelah MM, Zani F, Incerti M, Cavazzoni A, Alfieri RR, Petronini PG, Vicini P. Bioorg. Med. Chem. 2010; 18: 5873 5d Gaddam V, Ramesh S, Nagarajan R. Tetrahedron 2010; 66: 4218 5e Bouclé S, Guillard J. Synthesis 2011; 1616 5f Chaitanya TK, Nagarajan R. Org. Biomol. Chem. 2011; 9: 4662 5g Jella RR, Nagarajan R. Synlett 2011; 529 6 Stiborová M, Rupertová M, Schmeiser Heinz H, Frei E. Biomed. Pap. Med. Fac. Univ. Palacky Olomouc Czech. Repub. 2006; 150: 13 (7) 7a Marsais F, Pineau P, Nivolliers F, Mallat M, Turck A, Godard A, Queguiner G. J. Org. Chem. 1992; 57: 565 7b Gribble GW, Saulnier MG, Sibi MP, Obaza-Nutaitis JA. J. Org. Chem. 1984; 49: 4518 7c Alvarez M, Joule JA In The Chemistry of Heterocyclic Compounds . Saxton JE. Wiley; Chichester, UK: 1994: 261-278 7d Ishikura M, Hino A, Yaginuma T, Agata I, Katagiri N. Tetrahedron 2000; 56: 193 7e Mal D, Senapati BK, Pahari P. Synlett 2005; 994 7f Miki Y, Hachiken H, Yanase N. Org. Biomol. Chem. 2001; 2213 8 Ohashi M, Oki T. Exp. Opin. Ther. Patents 1996; 6: 1285 9a Weinkauf RL, Chen AY, Yu C, Liu L, Barrows L, Voie E. J. Bioorg. Med. Chem. 1994; 2: 781 9b Fidesser E, Haider N, Jbara R. ARKIVOC 2001; (v): 133 10 Vilsmeier A, Haack A. Ber. Dtsch. Chem. Ges. 1927; 60: 119 11a Fujisawa T, Lida S, Sato T. Chem. Lett. 1984; 1173 11b Newman MS, Sujeeth PK. J. Org. Chem. 1978; 43: 4367 11c Boeckman RK. Jr, Ganem B. Tetrahedron Lett. 1974; 15: 913 12 Venugopal M, Umarani R, Perumal PT, Rajadurai S. Tetrahedron Lett. 1991; 32: 3235 13 Rao MS. C, Rao GS. K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1988; 27: 213 14a Meth-Cohn O, Narine AB. Tetrahedron Lett. 1978; 23: 2045 14b Khan AK, Shoeb A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985; 24: 62 15a Sreenivasulu M, Rao KG. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1989; 28: 584 15b Mahata PK, Venkatesh C, Syam Kumar UK, Ila H, Junjappa H. J. Org. Chem. 2003; 68: 3966 15c Chupp JP, Metz S. J. Heterocycl. Chem. 1979; 16: 65 15d Katrtizky AR, Arend M. J. Org. Chem. 1998; 63: 9989 16a Harrowven DC, Setton BJ, Coulton S. Tetrahedron Lett. 2001; 42: 2907 16b Katritzky AR, Arend MJ. J. Org. Chem. 1998; 63: 9989 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. Zusatzmaterial Zusatzmaterial Supporting Information (PDF) (opens in new window)
