An efficient route to diverse H-pyrazolo[5,1-a]isoquinolines via sequential multi-component/cross-coupling reactions

Tetrahedron

Volumn 67, Issue 6, 2011, Pages 1145-1149

  Yu, Xingxin ^a   Pan, Xiaolin ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

2 Alkynylbenzaldehyde; Cross coupling reaction; Electrophile; H Pyrazolo 5,1 a isoquinoline; Multi component reaction

Indexed keywords

BENZALDEHYDE DERIVATIVE; BROMINE; ELECTROPHILE; HYDRAZIDE DERIVATIVE; IODINE; ISOQUINOLINE DERIVATIVE; KETONE; PALLADIUM COMPLEX; PYRAZOLONE DERIVATIVE;

AROMATIZATION; ARTICLE; CROSS COUPLING REACTION; CYCLIZATION; ONE POT SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 78751569589     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.12.005     Document Type: Article

References (77)

1. For selected examples, see:
2. K.W. Bentley The Isoquinoline Alkaloids Vol. 1 1998 Harwood Academic Australia
3. J.D. Phillipson, M.F. Roberts, and M.H. Zenk The Chemistry and Biology of Isoquinoline Alkaloids 1985 Springer New York, NY
4. For selected examples, see:
5. B.W. Trotter, K.K. Nanda, N.R. Kett, C.P. Regan, J.J. Lynch, G.L. Stump, L. Kiss, J. Wang, R.H. Spencer, S.A. Kane, R.B. White, R. Zhang, K.D. Anderson, N.J. Liverton, C.J. McIntyre, D.C. Beshore, G.D. Hartman, and C.J. Dinsmore J. Med. Chem. 49 2006 6954
6. P. Ramesh, N.S. Reddy, and Y. Venkateswarlu J. Nat. Prod. 62 1999 780
7. T. Kaneda, Y. Takeuchi, H. Matsui, K. Shimizu, N. Urakawa, and S. Nakajyo J. Pharm. Sci. 98 2005 275
8. Y. Mikami, K. Yokoyama, H. Tabeta, K. Nakagaki, and T. Arai J. Pharm. Dyn. 4 1981 282
9. C. Marchand, S. Antony, K.W. Kohn, M. Cushman, A. Ioanoviciu, B.L. Staker, A.B. Burgin, L. Stewart, and Y. Pommier Mol. Cancer Ther. 5 2006 287
10. G.R. Pettit, V. Gaddamidi, D.L. Herald, S.B. Singh, G.M. Cragg, J.M. Schmidt, F.E. Boettner, M. Williams, and Y. Sagawa J. Nat. Prod. 49 1986 995
11. C. Bailly Curr. Med. Chem.: Anti-Cancer Agents 4 2004 363
12. E. Marco, W. Laine, C. Tardy, A. Lansiaux, M. Iwao, F. Ishibashi, C. Bailly, and F. Gago J. Med. Chem. 48 2005 3796
13. M.V.R. Reddy, M.R. Rao, D. Rhodes, M.S.T. Hansen, K. Rubins, F.D. Bushman, Y. Venkateswarlu, and D.J. Faulkner J. Med. Chem. 42 1999 1901
14. A. Aubry, X.-S. Pan, L.M. Fisher, V. Jarlier, and E. Cambau Antimicrob. Agents Chemother. 48 2004 1281
15. D.P. Walsh, and Y.-T. Chang Chem. Rev. 106 2006 2476
16. P. Arya, D.T.H. Chou, and M.-G. Baek Angew. Chem., Int. Ed. 40 2001 339
17. S.L. Schreiber Science 287 2000 1964
18. C. Pinilla, J.R. Appel, and R.A. Houghten Nature Med. 9 2003 118
19. For reviews, see:
20. J. Montgomery Angew. Chem., Int. Ed. 43 2004 3890
21. E. Negishi, C. Coperet, S. Ma, S.Y. Liou, and F. Liu Chem. Rev. 96 1996 365
22. L.F. Tietze Chem. Rev. 96 1996 115
23. R. Grigg, and V. Sridharan J. Organomet. Chem. 576 1999 65
24. T. Miura, and M. Murakami Chem. Commun. 2007 217
25. M. Malacria Chem. Rev. 96 1996 289
26. K.C. Nicolaou, T. Montagnon, and S.A. Snyder Chem. Commun. 2003 551
27. K.C. Nicolaou, D.J. Edmonds, and P.G. Bulger Angew. Chem., Int. Ed. 45 2006 7134
28. D. Enders, C. Grondal, and M.R.M. Hüttl Angew. Chem., Int. Ed. 46 2007 1570
29. L.F. Tietze, G. Brasche, and K. Gericke Domino Reactions in Organic Synthesis 2006 Wiley-VCH Weinheim, Germany
30. X. Yu, Z. Chen, X. Yang, and J. Wu J. Comb. Chem. 12 2010 374
31. X. Yu, S. Ye, and J. Wu Adv. Synth. Catal. 352 2010 2050
32. For selected examples, see:
33. Z. Chen, X. Yang, and J. Wu Chem. Commun. 2009 3469
34. Z. Chen, Q. Ding, X. Yu, and J. Wu Adv. Synth. Catal. 351 2009 1692
35. X. Yu, X. Yang, and J. Wu Org. Biomol. Chem. 7 2009 4526
36. Z. Chen, M. Su, X. Yu, and J. Wu Org. Biomol. Chem. 7 2009 4641
37. Q. Ding, Z. Chen, X. Yu, Y. Peng, and J. Wu Tetrahedron Lett. 50 2009 340
38. X. Yu, Q. Ding, Z. Chen, and J. Wu Tetrahedron Lett. 50 2009 4279
39. Z. Chen, and J. Wu Org. Lett. 12 2010 4856
40. S. Ye, X. Yang, and J. Wu Chem. Commun. 46 2010 5238
41. Z. Chen, X. Yu, and J. Wu Chem. Commun. 46 2010 6356
42. H. Ren, S. Ye, F. Liu, and J. Wu Tetrahedron 66 2010 8242
43. Selected examples for metal-catalyzed cyclization of 2- alkynylbenzaldehyde:
44. A.B. Beeler, S. Su, C.A. Singleton, and J.A. Porco Jr. J. Am. Chem. Soc. 129 2007 1413 and references cited therein
45. N. Asao Synlett 2006 1645
46. I. Nakamura, Y. Mizushima, I.D. Gridnev, and Y. Yamamoto J. Am. Chem. Soc. 127 2005 9844
47. N. Kim, Y. Kim, W. Park, D. Sung, A.-K. Gupta, and C.-H. Oh Org. Lett. 7 2005 5289
48. K. Sato, N. Asao, and Y. Yamamoto J. Org. Chem. 70 2005 8977
49. N. Asao, K. Sato, Menggenbateer, and Y. Yamamoto J. Org. Chem. 70 2005 3682
50. H. Kusama, H. Funami, J. Takaya, and N. Iwasawa Org. Lett. 6 2004 605
51. N. Asao, H. Aikawa, and Y. Yamamoto J. Am. Chem. Soc. 126 2004 7458
52. Q. Ding, and J. Wu Org. Lett. 9 2007 4959
53. K. Gao, and J. Wu J. Org. Chem. 72 2007 8611
54. W. Sun, Q. Ding, X. Sun, R. Fan, and J. Wu J. Comb. Chem. 9 2007 690
55. Y. Ohta, Y. Kubota, T. Watabe, H. Chiba, S. Oishi, N. Fujii, and H. Ohno J. Org. Chem. 74 2009 6299
56. X. Yu, and J. Wu J. Comb. Chem. 12 2010 238
57. Q. Ding, B. Wang, and J. Wu Tetrahedron 63 2007 12166
58. S. Ye, and J. Wu Tetrahedron Lett. 50 2009 6273
59. H. Zhou, H. Jin, S. Ye, X. He, and J. Wu Tetrahedron Lett. 50 2009 4616
60. X. Yu, Q. Ding, and J. Wu J. Comb. Chem. 12 2010 743
61. For selected examples of multi-component reactions, see:
62. J. Zhu, H. Bienayme, Multicomponent Reactions 2005 Wiley-VCH Weinheim, Germany
63. D.J. Ramon, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602
64. V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekenth, and L. Balagopal Acc. Chem. Res. 36 2003 899
65. R.V.A. Orru, and M. de Greef Synthesis 2003 1471
66. G. Balme, E. Bossharth, and N. Monteiro Eur. J. Org. Chem. 2003 4101
67. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168
68. H. Bienaymé, C. Hulme, G. Oddon, and P. Schmitt Chem. - Eur. J. 6 2000 3321
69. L. Weber, K. Illgen, and M. Almstetter Synlett 1999 366
70. I. Ugi, A. Domling, and B. Werner J. Heterocycl. Chem. 37 2000 647
71. J. Zhu Eur. J. Org. Chem. 2003 1133
72. C. Hulme, and V. Gore Curr. Med. Chem. 10 2003 51
73. L. Weber Curr. Med. Chem. 9 2002 1241
74. For recent reviews, see:
75. N. Miyaura Top. Curr. Chem. 219 2002 11
76. A. Suzuki J. Organomet. Chem. 576 1999 147
77. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176