I2-catalyzed reactions of Schiff base and alkyl aldehyde towards benzo[f]quinoline derivatives

Journal of Heterocyclic Chemistry

Volumn 45, Issue 4, 2008, Pages 1027-1031

  Wang, Xiang Shan ^a,b   Li, Qing ^a   Zhang, Mei Mei ^b   Yao, Chang Sheng ^a   Tu, Shu Jiang ^a,b  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYL GROUP; BENZO[F]QUINOLINE DERIVATIVE; IODINE; QUINOLINE DERIVATIVE; SCHIFF BASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; INFRARED SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 47749096814     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450412     Document Type: Article

References (39)

1. Brock, E. D.; Lewis, D. M.; Yousaf, T. I.; Harper, H. H. (The Procter and Gamble Company USA) W09951688, 1999.
2. [a] Beagley, P.; Blackie, M. A. L.; Chibale, K.; Clarkson, C.; Meijboom, R.; Moss, J. R.; Smith, P.; Su, H. Dalton Trans. 2003, 3046-3051.
3. [b] Sawada, Y.; Kayakiri, H.; Abe, Y.; Mizutani, T.; Inamura, N.; Asano, M.; Hatori, C.; Aramori, I.; Oku, T.; Tanaka, H. J. Med. Chem. 2004, 47, 2853-2863.
4. [c] Ma, Z.; Hano, Y.; Nomura, T.; Chen, Y. Bioorg. Med. Chem. Lett. 2004, 14, 1193-1196.
5. [d] Denton, T. T.; Zhang, X.; Cashman, J. R. J. Med. Chem. 2005, 48, 224-239.
6. [e] Fokialakis, N.; Magiatis, P.; Chinou, L.; Mitaku, S.; Tillequin, F. Chem. Pharm. Bull. 2002, 50, 413-414.
7. [f] Fossa, P.; Mosti, L.; Menozzi, G.; marzano, C.; Baccichetti, F.; Bordin, F. Bioorg. Med. Chem. 2002, 10, 743-751.
8. [g] Ryckebusch, A.; Derprez-Poulain, R.; Maes, L.; Debreu-Fontaine, M. A.; Mouray, E.; Grellier, P.; Sergheraert, C.; J. Med. Chem. 2003, 46, 542-557.
9. [h] Morgan, L. R.; Jursic, B. S.; Hooper, C. L.; Neumann, D. M.; Thangaraj, K.; Leblanc, B. Bioorg. Med. Chem. Lett. 2002, 12, 3407-3411.
10. Sakata, G.; Makino, K.; Karasawa, Y. Heterocycles 1988, 27, 2481-2515,
11. [a] Demeunynck, M.; Moucheron, C.; Mesmaeker, A. K.-D. Tetrahedron Lett. 2002, 43, 261-264;
12. [b] Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. Eur. J. Org. Chem. 1999, 937-941;
13. [c] Ali, M. M.; Tasneem, K. C.; Rajanna, P. K.; Prakash, S. Synlett 2001, 251-253;
14. [d] Palacios, F.; Ochoa de Retana, A. M.; Oyarzabal, J. Tetrahedron 1999, 55, 5947-5964;
15. [e] Charpentier, P.; Lobregat, V.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron Lett. 1998, 39, 4013-4016;
16. [f] Cho, C. S.; Kim, B. T.; Kim, T. J.; Shim, S. C. Chem. Commun. 2001, 2576-2577;
17. [g] Uchiyama, K.; Hayashi, Y.; Narasaka, K. Synlett 1997, 445-447;
18. [h] Crousse, B.; Begue, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009-5013;
19. [i] Lin, X. F.; Cui, S. L.; Wang, Y. G. Tetrahedron Lett. 2006, 47, 4509-4512.
20. [j] Lin, X. F.; Cui, S. L.; Wang, Y. G. Tetrahedron Lett. 2006, 47, 3127-3130.
21. [a] Skraup, H. Chem. Ber. 1880, 13, 2086-2087;
22. [b] Mansake, R. H.; Kulka, M. Org. React. 1953, 7, 59-61;
23. [c] Doebner, O.; Miller, V. W. Chem. Ber. 1881, 14, 2812-2813;
24. [d] Conrad, M.; Limbach, L. Chem. Ber. 1887, 20, 944-945;
25. [e] Combes, A. Compt. Rend. 1888, 106, 142-143;
26. [f] Pfitzinger, W. J. Prakt. Chem. 1886, 33, 100.
27. Whitmore, F. C.; Rothrock, H. S. J. Am. Chem. Soc. 1933, 55, 1106-1109.
28. Rutherford, K. G.; Marner, O. A.; Prokipcak, J. M.; Jobin, R. A. Can. J. Chem. 1966, 44, 2337-2339.
29. Jenner, G. Tetrahedron Lett. 1988, 29, 2445-2448. 15.
30. Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377-4380.
31. Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959-1961.
32. Sun, J.; Dong, Y.; Cao, L.; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932-8934.
33. Ramalinga, K.; Vijayalakshimi, P.; Kaimal, T. N. B. Tetrahedron Lett. 2002, 43, 879-882.
34. Chavan, S. P.; Kale, R. R.; Shivasankar, K.; Chandake, S. I.; Benjamin, S. B. Synthesis 2003, 2695-2698.
35. [a] Yadav, J. S.; Reddy, B. V. S.; Sadasiv, K.; Satheesh, G. Tetrahedron Lett. 2002, 43, 9695-9697;
36. [b] Wang, S. Y.; Ji, S. J.; Loh, T. P. Synlett 2003, 2377-2379.
37. [a] Ji, S. J.; Wang, S. Y.; Zhang, Y.; Loh, T. P. Tetrahedron 2004, 60, 2051-2055;
38. [b] Ke, B. W.; Qin, Y.; He, Q. F.; Huang, Z. Y.; Wang, F. P. Tetrahedron Lett. 2005, 46, 1751-1753.
39. -1. Intensity data were collected on Rigaku Mercury diffractometer with graphite monochromated MoKα radiation (λ = 0.71070 Å) using ω scan mode with 3.03° < θ < 25.35°. 3336 unique reflections were measured and 3034 reflections with I>2σ(I) were used in the refinement. Structure solved by direct methods and expanded using Fourier techniques. The final cycle of full-matrix least squares technique to R = 0.0423 and wR = 0.0814.