New domino reaction for the selective synthesis of tetracyclic cinnolino[5,4,3-cde]cinnolines

Organic and Biomolecular Chemistry

Volumn 7, Issue 6, 2009, Pages 1171-1175

  Jiang, Bo ^a,b   Hao, Wen Juan ^a   Zhang, Jin Peng ^c   Tu, Shu Jiang ^a,b   Shi, Feng ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b SUZHOU UNIVERSITY   (China)

^c XUZHOU MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC GROUPS; ARYL GROUPS; DOMINO REACTIONS; SELECTIVE SYNTHESIS; STERIC CONTROLS;

AMINES;

REACTION KINETICS;

CINNOLINE; CINNOLINO(5,4,3 CDE)CINNOLINE; CINNOLINO(5,4,3-CDE)CINNOLINE; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HETEROCYCLIC COMPOUNDS, 2-RING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 62249215766     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b817930a     Document Type: Article

References (49)

1. L. F. Tietze Chem. Rev. 1996 96 115
2. S. E. Denmark A. Thorarensen Chem. Rev. 1996 96 137
3. M. Malacria Chem. Rev. 1996 96 289
4. T. Schwier A. W. Sromek D. Chernyak V. Gevorgyan J. Am. Chem. Soc. 2007 129 9868
5. J. Barluenga A. Jimenez-Aquino C. Valdes F. Aznar Angew. Chem., Int. Ed. 2007 46 1529
6. H. Waldmann M. Kuhn W. Liu K. Kumar Chem. Commun. 2008 1211
7. A. de Meijere P. von Zezschwitz S. Bräse Acc. Chem. Res. 2005 38 413
8. L. F. Tietze and G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006
9. A. Domling I. Ugi Angew. Chem., Int. Ed. 2000 39 3168
10. A. Diguez-Vzquez C. C. Tzschucke W. Y. Lam S. V. Le Angew. Chem., Int. Ed. 2008 47 209
11. F. L. Muller T. Constantieux J. Rodriguez J. Am. Chem. Soc. 2005 127 17176
12. H. Ischikawa, T. Umeda and K. Kajikawa, Jpn. Patent 04187677; Chem. Abstr. 117, 165929 g, 1992
13. J. Labovitz, W. Guilford, Y. Liang, L. Fang and T. Patterson, Eur. Patent 363236; Chem. Abstr. 113, 226421b, 1990
14. M. Mizutani, M. Shiroshita, H. Okuda, N. Mito and M. Sakaki, Eur. Patent 320782; Chem. Abstr.112, 114186b, 1989
15. T. G. Patterson, V S Patent 5129940; Chem. Abstr.117, 186659j, 1992
16. M. J. Coghlan, B. A. Driekorn, R. G. Suhr and G. P. Jourdan, Eur. Patent 326328, Chem. Abstr. 112, 55907u, 1989
17. M. Mizutani, M. Shiroshita, M. Sakaki, N. Mito and H. Okuda, Eur. Patent 320793; Chem. Abstr. 111, 232847v, 1989
18. D. Munro, and R. A. Bit, UK Patent 2189238; Chem. Abstr. 108, 150499 g, 1987
19. S. Inoue, A. Yasaki, H. Mochizuki, H. Tutsumi, M. Murata and K. Sakane, Jpn. Patent 05213951; Chem. Abstr. 120, 134503w, 1993
20. H. Tutsumi, T. Terasawa, D. Barret, M. Mutata, K. Sakane, A. Yazaki and S. Inoue, Jpn. Patent 9215584 Chem. Abstr. 118, 254944w, 1992
21. M. Yokomoto, A. Yazaki, N. Hayashi, S. Hatono, S. Inoue and Y. Kuramoto, Eur. Patent 4700578; Chem. Abstr. 117, 7943c, 1992
22. K. Miyamoto, J. Matsumoto, and S. Nakamura, Jpn. Patent 02096570; Chem. Abstr. 113, 97619w, 1990
23. J. K. Stille R. Ertz J. Am. Chem. Soc. 1964 86 661
24. J. K. Stille J. M. Unglaube M. E. Freeburger J. Am. Chem. Soc. 1968 90 7076
25. S. J. Tu B. Jiang R. H. Jia J. Y. Zhang Y. Zhang C. S. Yao F. Shi Org. Biomol. Chem. 2006 4 3664
26. S. J. Tu B. Jiang J. Y. Zhang R. H. Jia Y. Zhang C. S. Yao Org. Biomol. Chem. 2006 4 3980
27. S. J. Tu B. Jiang Y. Zhang R. H. Jia J. Y. Zhang C. S. Yao F. Shi Org. Biomol. Chem. 2007 5 355
28. S. J. Tu C. M. Li G. G. Li L. J. Cao Q. Q. Shao D. X. Zhou B. Jiang J. F. Zhou M. Xia J. Comb. Chem. 2007 9 1144
29. E. C. Horning M. G. Horning J. Org. Chem. 1946 11 95
30. J. Baldas Q. N. Porter Tetrahedron Lett. 1968 11 1351
31. H. Hagiwara A. Numamae K. Isobe T. Hoshi T. Suzuki Heterocycles 2006 68 889
32. K. Singh J. Singh H. Singh Tetrahedron 1996 52 14273
33. V. Hegde C. Y. Hung P. Madhukar R. Cunningham T. Hopfner R. P. Thummel J. Am. Chem. Soc. 1993 115 872
34. Y. M. Shchekotikhin T. G. Nikolaeva Chem. Heterocycl. Compd. 2006 42 28
35. S. J. Tu J. F. Zhou Z. S. Lu X. Deng D. Q. Shi S. H. Wang Synth. Commun. 2002 32 3063
36. S. J. Tu J. P. Zhang X. T. Zhu J. N. Xu Q. Wang Acta Cryst. E61 2005 o4082
37. S. J. Tu J. P. Zhang X. T. Zhu J. N. Xu Q. Wang Acta Cryst. E61 2005 o1491
38. D. J. Triggle Cell. Mol. Neurobiol. 2003 23 293
39. S. Goldmann J. Stoltefuss Angew. Chem., Int. Ed. Engl. 1991 30 1559
40. V. T. Ramakrishnan G. Kathiravan J. Muthumary T. Josephrajan ARKIVOC 2005 (xi) 124 136
41. B. Love M. Goodmann K. Snader R. Tedeschi E. Macko J. Med. Chem. 1974 17 956
42. C. F. Bernasconi Tetrahedron 1989 45 4017
43. F. Liang J. Zhang J. Tan Q. Liu Adv. Synth. Catal. 2006 348 1986
44. B. C. Milgram K. Eskildsen S. M. Richter W. R. Scheidt K. A. Scheidt J. Org. Chem. 2007 72 3941
45. Y. Endo T. Uchida K. Shudo Tetrahedron Lett. 1997 38 2113
46. T. Ryckmans H.-G. Viehe Tetrahedron 1997 53 1729
47. P. F. Santos N. Srinivasan P. S. Almeida A. M. Lobo S. Prabhakar Tetrahedron 2005 61 9147
48. G. Mass C. Hummel Chem. Ber. 1980 113 3679
49. V. Lukes M. Breza D. Vegh P. Hrdlovic J. Krajcovic V. Laurinc Synth. Met. 2002 129 85