Silver triflate-catalyzed three-component reaction of 2- alkynylbenzaldehyde, sulfonohydrazide, and α,β-unsaturated carbonyl compound

Chemical Communications

Volumn 46, Issue 29, 2010, Pages 5238-5240

  Ye, Shengqing ^a   Yang, Xiaodi ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 ALKYNYLBENZALDEHYDE; BENZALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; H PYRAZOLO[5,1 A]ISOQUINOLINE 1 CARBOXYLIC ACID DERIVATIVE; HYDRAZIDE DERIVATIVE; SILVER DERIVATIVE; SILVER TRIFLATE; SULFONOHYDRAZIDE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 77954711939     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0cc00905a     Document Type: Article

References (86)

1. Multicomponent Reactions, ed., J. Zhu, and, H. Bienayme, Wiley-VCH, Weinheim, Germany, 2005
2. D. J. Ramon M. Yus Angew. Chem., Int. Ed. 2005 44 1602
3. V. Nair C. Rajesh A. U. Vinod S. Bindu A. R. Sreekenth L. Balagopal Acc. Chem. Res. 2003 36 899
4. R. V. A. Orru M. D. Greef Synthesis 2003 1471
5. G. Balme E. Bossharth N. Monteiro Eur. J. Org. Chem. 2003 4101
6. A. Domling I. Ugi Angew. Chem., Int. Ed. 2000 39 3168
7. H. Bienayme C. Hulme G. Oddon P. Schmitt Chem.-Eur. J. 2000 6 3321
8. L. Weber K. Illgen M. Almstetter Synlett 1999 366
9. I. Ugi A. Domling B. Werner J. Heterocycl. Chem. 2000 37 647
10. J. Zhu Eur. J. Org. Chem. 2003 1133
11. C. Hulme V. Gore Curr. Med. Chem. 2003 10 51
12. L. Weber Curr. Med. Chem. 2002 9 1241
13. A. Ulaczyk-Lesanko D. G. Hall Curr. Opin. Chem. Biol. 2005 9 266
14. Q. Huang R. C. Larock J. Org. Chem. 2003 68 980
15. G. Dai R. C. Larock J. Org. Chem. 2003 68 920
16. G. Dai R. C. Larock J. Org. Chem. 2002 67 7042
17. Q. Huang J. A. Hunter R. C. Larock J. Org. Chem. 2002 67 3437
18. K. R. Roesch R. C. Larock J. Org. Chem. 2002 67 86
19. K. R. Roesch H. Zhang R. C. Larock J. Org. Chem. 2001 66 8042
20. K. R. Roesch R. C. Larock Org. Lett. 1999 1 553
21. G. Dai R. C. Larock Org. Lett. 2001 3 4035
22. M. Balasubramanian and J. G. Keay, Isoquinoline Synthesis, in Comprehensive Heterocyclic Chemistry II, ed., A. E. McKillop, A. R. Katrizky, C. W. Rees, and, E. F. V. Scrivem, Elsevier, Oxford, 1996, vol. 5, p. 245
23. M. Chrzanowska M. D. Rozwadowska Chem. Rev. 2004 104 3341
24. Y.-N. Niu Z.-Y. Yan G.-L. Gao H.-L. Wang X.-Z. Shu K.-G. Ji Y.-M. Lang J. Org. Chem. 2009 74 2893
25. Y.-Y. Yang W.-G. Shou Z.-B. Chen D. Hong Y.-G. Wang J. Org. Chem. 2008 73 3928
26. D. Fischer H. Tomeba N. K. Pahadi N. T. Patil Z. Huo Y. Yamamoto J. Am. Chem. Soc. 2008 130 15720
27. M. Movassaghi M. D. Hill Org. Lett. 2008 10 3485
28. T. Blackburn Y. K. Ramtohul Synlett 2008 1159
29. G. Pandey M. Balakrishnan J. Org. Chem. 2008 73 8128
30. S. Su J. A. Porco Org. Lett. 2007 9 4983
31. M. Mori H. Wakamatsu K. Tonogaki R. Fujita T. Kitamura Y. Sato J. Org. Chem. 2005 70 1066
32. Z. Xiang T. Luo K. Lu J. Cui X. Shi R. Fathi J. Chen Z. Yang Org. Lett. 2004 6 3155
33. B. K. Ghorai S. Duan D. Jiang J. W. Herndon Synthesis 2006 3661
34. F. Palacios C. Alonso M. Rodríguez E. Martinez de Marigorta G. Rubiales Eur. J. Org. Chem. 2005 1795
35. F. Palacios C. Alonso G. Rubiales M. Villegas Tetrahedron 2005 61 2779
36. T. K. Sarkar N. Panda S. Basak J. Org. Chem. 2003 68 6919
37. P. R. Carly T. C. Govaerts S. L. Cappelle F. Compernolle G. J. Hoornaert Tetrahedron 2001 57 4203
38. T. K. Sarkar S. K. Ghosh T. J. Chow J. Org. Chem. 2000 65 3111
39. P. R. Carly S. L. Cappelle F. Compernolle G. J. Hoornaert Tetrahedron 1996 52 11889
40. Z. Chen X. Yu M. Su X. Yang J. Wu Adv. Synth. Catal. 2009 351 2702
41. Q. Ding Z. Wang J. Wu J. Org. Chem. 2009 74 921
42. Q. Ding J. Wu Adv. Synth. Catal. 2008 350 1850
43. Q. Ding Z. Wang J. Wu Tetrahedron Lett. 2009 50 198
44. M. V. R. Reddy M. R. Rao D. Rhodes M. S. T. Hansen K. Rubins F. D. Bushman Y. Venkateswarlu D. J. Faulkner J. Med. Chem. 1999 42 1901
45. A. Aubry X.-S. Pan L. M. Fisher V. Jarlier E. Cambau Antimicrob. Agents Chemother. 2004 48 1281
46. E. Marco W. Laine C. Tardy A. Lansiaux M. Iwao F. Ishibashi C. Bailly F. Gago J. Med. Chem. 2005 48 3796
47. C. Bailly Curr. Med. Chem.: Anti-Cancer Agents 2004 4 363
48. A. B. Beeler S. Su C. A. Singleton J. A. Porco, Jr. J. Am. Chem. Soc. 2007 129 1413
49. N. Asao Synlett 2006 1645
50. I. Nakamura Y. Mizushima I. D. Gridnev Y. Yamamoto J. Am. Chem. Soc. 2005 127 9844
51. N. Kim Y. Kim W. Park D. Sung A.-K. Gupta C.-H. Oh Org. Lett. 2005 7 5289
52. K. Sato N. Asao Y. Yamamoto J. Org. Chem. 2005 70 8977
53. N. Asao K. Sato Menggenbateer Y. Yamamoto J. Org. Chem. 2005 70 3682
54. H. Kusama H. Funami J. Takaya N. Iwasawa Org. Lett. 2004 6 605
55. N. Asao H. Aikawa Y. Yamamoto J. Am. Chem. Soc. 2004 126 7458
56. N. Asao H. Aikawa Y. Yamamoto J. Am. Chem. Soc. 2004 126 7458
57. Q. Ding J. Wu Org. Lett. 2007 9 4959
58. K. Gao J. Wu J. Org. Chem. 2007 72 8611
59. W. Sun Q. Ding X. Sun R. Fan J. Wu J. Comb. Chem. 2007 9 690
60. Q. Ding B. Wang J. Wu Tetrahedron 2007 63 12166
61. Y. Ohta Y. Kubota T. Watabe H. Chiba S. Oishi N. Fujii H. Ohno J. Org. Chem. 2009 74 6299
62. J. Montgomery Angew. Chem., Int. Ed. 2004 43 3890
63. E. Negishi C. Coperet S. Ma S. Y. Liou F. Liu Chem. Rev. 1996 96 365
64. L. F. Tietze Chem. Rev. 1996 96 115
65. R. Grigg V. Sridharan J. Organomet. Chem. 1999 576 65
66. T. Miura M. Murakami Chem. Commun. 2007 217
67. M. Malacria Chem. Rev. 1996 96 289
68. K. C. Nicolaou T. Montagnon S. A. Snyder Chem. Commun. 2003 551
69. K. C. Nicolaou D. J. Edmonds P. G. Bulger Angew. Chem., Int. Ed. 2006 45 7134
70. D. Enders C. Grondal M. R. M. Hüttl Angew. Chem., Int. Ed. 2007 46 1570
71. L. F. Tietze, G. Brasche and K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2006
72. Z. Chen X. Yang J. Wu Chem. Commun. 2009 3469
73. Z. Chen Q. Ding X. Yu J. Wu Adv. Synth. Catal. 2009 351 1692
74. X. Yu X. Yang J. Wu Org. Biomol. Chem. 2009 7 4526
75. Z. Chen M. Su X. Yu J. Wu Org. Biomol. Chem. 2009 7 4641
76. X. Yu Q. Ding Z. Chen J. Wu Tetrahedron Lett. 2009 50 4279
77. X. Yu Z. Chen X. Yang J. Wu J. Comb. Chem. 2010 12 374
78. I. Coldham R. Hufton Chem. Rev. 2005 105 2765
79. C. Najera J. M. Sansano Angew. Chem., Int. Ed. 2005 44 6272
80. C. Najera J. M. Sansano Curr. Org. Chem. 2003 7 1105
81. S. Kobayashi K. Nishio J. Org. Chem. 1994 59 6620
82. C. Ogawa M. Sugiura S. Kobayashi Chem. Commun. 2003 192
83. S. Kobayashi R. Hirabayashi J. Am. Chem. Soc. 1999 121 6942
84. R. Hirabayashi C. Ogawa M. Sugiura S. Kobayashi J. Am. Chem. Soc. 2001 123 9493
85. C. Ogawa M. Sugiura S. Kobayashi J. Org. Chem. 2002 67 5359
86. J. Wu X. Sun H.-G. Xia Eur. J. Org. Chem. 2005 4769