Stepwise and one-pot cross-coupling-heteroannulation approaches toward 2-substituted C5-, C6-, and C7-nitroindoles

Tetrahedron

Volumn 60, Issue 48, 2004, Pages 10983-10992

  Sun, Li Ping ^b   Huang, Xiang Hong ^b   Dai, Wei Min ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

2 Aminophenols; Aryl triflates; Cross coupling; Heteroannulation; Nitroindoles

Indexed keywords

5 NITRO 2 (2' HYDROXYETHYL)INDOLE; 5 NITRO 2 (3' CHLOROPROPYL)INDOLE; 5 NITRO 2 (3' CYANOPROPYL)INDOLE; 5 NITRO 2 PHENYLINDOLE; 5 NITRO 2 PROPYLINDOLE; 6 NITRO 2 (2' HYDROXYETHYL)INDOLE; 6 NITRO 2 (3' CHLOROPROPYL)INDOLE; 6 NITRO 2 (3' CYANOPROPYL)INDOLE; 6 NITRO 2 PHENYLINDOLE; 6 NITRO 2 PROPYLINDOLE; 7 NITRO 2 (2' HYDROXYETHYL)INDOLE; 7 NITRO 2 PHENYLINDOLE; 7 NITRO 2 PROPYLINDOLE; ALKYNE; ANILIDE; FLUORINE DERIVATIVE; INDOLE DERIVATIVE; NITRO DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 14544308904     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.034     Document Type: Article

References (123)

1. V. Leclerc, S. Yous, P. Delagrange, J.A. Boutin, P. Renard, and D. Lesieur J. Med. Chem. 45 2002 1853 1859
2. P. Schoeffter, J.R. Floyd, A. Stoll, H. Siegl, M.P. Seiler, and D. Hoyer Eur. J. Pharmacol. 244 1993 251 257
3. M.A. Rea, J. Barrera, J.D. Glass, and R.L. Gannon Neuroreport 6 1995 1417 1420
4. A. Molla, and W.E. Kohlbrenner J.A. Bristol Annual Reports in Medicinal Chemistry Vol. 32 1997 Academic San Diego 131
5. R.L. Bell, J.B. Summers, and R.R. Harris J.A. Bristol Annual Reports in Medicinal Chemistry Vol. 32 1997 Academic San Diego 92
6. P. Galatsis J.A. Bristol Annual Reports in Medicinal Chemistry Vol. 32 1997 Academic San Diego 321
7. A.J. Robichaud, and B.L. Largent A.M. Doherty Annual Reports in Medicinal Chemistry Vol. 35 2000 Academic San Diego 13
8. Y.-C. Xu, K.W. Johnson, L.A. Phebus, M. Cohen, D.L. Nelson, K. Schenck, C.D. Walker, J.E. Fritz, S.W. Kaldor, M.E. LeTourneau, R.E. Murff, J.M. Zgombick, D.O. Calligaro, J.E. Audia, and J.M. Schaus J. Med. Chem. 44 2001 4031 4034
9. Q. Li, H.L. Sham, and S.H. Rosenberg A.M. Doherty Annual Reports in Medicinal Chemistry Vol. 34 1999 Academic San Diego 145 146
10. T. Owa, H. Yoshino, T. Okauchi, K. Yoshimatsu, Y. Ozawa, N.H. Sugi, T. Nagasu, N. Koyanagi, and K. Kitoh J. Med. Chem. 42 1999 3789 3799
11. T. Owa, T. Okauchi, K. Yoshimatsu, N.H. Sugi, Y. Ozawa, T. Nagasu, N. Koyanagi, T. Okabe, K. Kitoh, and H. Yoshino Bioorg. Med. Chem. Lett. 10 2000 1223 1226
12. O. Ottoni, R. Cruz, and N.H. Krammer Tetrahedron Lett. 40 1999 1117 1120
13. E.T. Pelkey, and G.W. Gribble Synthesis 1999 1117 1122
14. J. Jiang, and G.W. Gribble Tetrahedron Lett. 43 2002 4115 4117
15. G.W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045 1075
16. G.W. Gribble Contemp. Org. Synth. 1994 145 172
17. D.W. Ockenden, and K.J. Schofield J. Chem. Soc. 1957 3175
18. C.M. Atkinson, J.C.E. Simpson, and A. Taylor J. Chem. Soc. 1945 530
19. I.I. Grandberg, L.D. Belyaeva, L.D. Dmitriev, and L.B. Dmitriev Khim. Geterotsikl. Soed. (Russ) 37 1973 37
20. H. Singer, and W. Shive J. Org. Chem. 22 1957 84 85
21. S.M. Parmerter, G. Cook, and W.B. Dixon J. Am. Chem. Soc. 80 1958 4621 4622
22. B.G. Szczepankiewicz, and C.H. Heathcock Tetrahedron 53 1997 8853 8870
23. J. Bergman, P. Sand, and U. Tilstam Tetrahedron Lett. 24 1983 3665 3668
24. J. Bergman, and P. Sand Tetrahedron 46 1990 6085 6112
25. L.L. Melhado, and J.L. Brodsky J. Org. Chem. 53 1988 3852 3855
26. K. Kato, M. Ono, and H. Akita Tetrahedron Lett. 38 1997 1805 1808
27. J.K. Sutherland Chem. Commun. 1997 325
28. E.T. Pelkey, and G.W. Gribble Tetrahedron Lett. 38 1997 5603 5606
29. R. ten Have, and A.M. van Leusen Tetrahedron 54 1998 1913 1920
30. N. Moskalev, and M. Makosza Tetrahedron Lett. 40 1999 5395 5398
31. N. Moskalev, M. Barbasiewicz, and M. Makosza Tetahedron 60 2004 347 358
32. F. Diederich P.J. Stang Metal-Catalyzed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim
33. J. Tsuji Palladium Reagents and Catalysts 1995 Wiley Chichester
34. J.J. Li, and G.W. Gribble Palladium in Heterocyclic Chemistry 2000 Pergamon Amsterdam
35. The Sonogashira cross-coupling reaction, see: (a) K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 1975 4467 4470
36. K. Sonogashira B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon New York 521 549
37. R. Rossi, A. Carpita, and F. Bellina Org. Prep. Proc. Int. 27 1995 127 160
38. For a recent review on Pd-catalyzed annulation, see: R.C. Larock J. Organomet. Chem. 576 1999 111 124
39. For Pd(II)-catalyzed cyclization of 2-alkynylanilines, see: (a) K. Utimoto, H. Miwa, and H. Nozaki Tetrahedron Lett. 22 1981 4277 4278
40. K. Utimoto Pure Appl. Chem. 55 1983 1845 1852
41. E.C. Taylor, A.H. Katz, H. Salgado-Zamore, and A. McKillop Tetrahedron Lett. 26 1985 5963 5966
42. M.E. Krolski, A.F. Renaldo, D.E. Rudisill, and J.K. Stille J. Org. Chem. 53 1988 1170 1176
43. K. Iritani, S. Matsubara, and K. Utimoto Tetrahedron Lett. 29 1988 1799 1802
44. A. Arcadi, S. Cacchi, and F. Marinelli Tetrahedron Lett. 30 1989 2581 2584
45. D. Rudisill, and J.K. Stille J. Org. Chem. 54 1989 5856 5866
46. Y.K. Kondo, T. Sakamoto, and H. Yamanaka Hetrocycles 29 1989 1013 1016
47. Y. Fukuda, S. Matsubara, and K. Utimoto J. Org. Chem. 56 1991 5812 5816
48. T. Jeschke, D. Wensbo, U. Annby, S. Gronowitz, and L. Cohen Tetrahedron Lett. 34 1993 6471 6474
49. Y. Kondo, N. Shiga, N. Murata, T. Sakamoto, and H. Yamanaka Tetrahedron 50 1994 11803 11812
50. S. Cacchi, V. Carnicelli, and F. Marinelli J. Organomet. Chem. 475 1994 289 296
51. K. Samizu, and K. Ogasawara Heterocycles 41 1995 1627 1629
52. M.S. Yu, L.L. de Leon, M.A. McGuire, and G. Botha Tetrahedron Lett. 39 1998 9347 9350
53. B.C.J. van Esseveldt, F.L. van Delft, R. de Gelder, and F.P.J.T. Rutjes Org. Lett. 5 2003 1717 1720
54. For a microwave-assisted solid-phase indole synthesis, see: (p) W.-M. Dai, D.-S. Guo, L.-P. Sun, and X.-H. Huang Org. Lett. 5 2003 2919 2922
55. Also see: (q) A. Takeda, S. Kamijo, and Y. Yamamoto J. Am. Chem. Soc. 122 2000 5662 5663
56. For Pd(0)-Cu(I)-catalyzed cyclization of 2-alkynylanilines, see: (a) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka Chem. Pharm. Bull. 36 1988 1305 1308
57. L. Xu, I.R. Lewis, S.K. Davidsen, and J.B. Summers Tetrahedron Lett. 39 1998 5159 5162
58. Synthesis on solid support, see: (c) H.-C. Zhang, K.K. Brumfield, L. Jaroskova, and B.E. Maryanoff Tetrahedron Lett. 39 1998 4449 4452
59. H.-C. Zhang, H. Ye, A.F. Moretto, K.K. Brumfield, and B.E. Maryanoff Org. Lett. 2 2000 89 92
60. For Cu(I)-catalyzed cyclization of 2-alkynylanilines, see: (a) C.E. Castro, and R.D. Stephens J. Org. Chem. 28 1963 2163 2164
61. C.E. Castro, E.J. Gauhan, and D.C. Owsley J. Org. Chem. 31 1966 4071 4078
62. D. Villemin, and D. Goussu Heterocycles 29 1989 1255 1261
63. V. Kumar, A.A. Dority, E.R. Bacon, B. Singh, and G.Y. Lesher J. Org. Chem. 57 1992 6995 6998
64. A.R. Katritzky, J. Li, and C.V. Stevens J. Org. Chem. 60 1995 3401 3404
65. J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M.A. García-Martín, and J.M. González J. Org. Chem. 61 1996 5804 5812
66. J. Soloducho Tetrahedron Lett. 40 1999 2429 2430
67. S. Cacchi, G. Fabrizi, and L.M. Parisi Org. Lett. 5 2003 3843 3846
68. For Cu(II)-catalyzed cyclization of 2-alkynylanilines, see: (a) M.G. Saulnier, D.B. Frennesson, M.S. Deshpande, and D.M. Vyas Tetrahedron Lett. 36 1995 7841 7844
69. K. Hiroya, S. Itoh, M. Ozawa, Y. Kanamori, and T. Sakamoto Tetrahedron Lett. 43 2002 1277 1280
70. K. Hiroya, S. Itoh, and T. Sakamoto J. Org. Chem. 69 2004 1126 1136 For a microwave-assisted solid-phase indole synthesis, see Ref. 15p
71. 5-catalyzed cyclization of 2-alkynylanilines, see: (a) F.E. McDonald, and A.K. Chatterjee Tetrahedron Lett. 38 1997 7687 7690
72. F.E. McDonald Chem. Eur. J. 5 1999 3103 3106
73. Alkoxide-catalyzed cyclization of 2-alkynylanilines, see: (a) T. Sakamoto, Y. Kondo, and H. Yamanaka Heterocycles 24 1986 31 32
74. T. Sakamoto, Y. Kondo, and H. Yamanaka Heterocycles 24 1986 1845 1847
75. T. Sakamoto, Y. Kondo, S. Iwashita, and H. Yamanaka Chem. Pharm. Bull. 35 1987 1823 1828
76. T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka Chem. Pharm. Bull. 36 1988 1305 1308
77. K. Shin, and K. Ogasawara Synlett 1995 859 860
78. Y. Kondo, S. Kojima, and T. Sakamoto Heterocycles 43 1996 2741 2746
79. Y. Kondo, S. Kojima, and T. Sakamoto J. Org. Chem. 62 1997 6507 6511
80. A.L. Rodriguez, C. Koradin, W. Dohle, and P. Knochel Angew. Chem. Int. Ed. 39 2000 2488 2490
81. W.-M. Dai, D.-S. Guo, and L.-P. Sun Tetrahedron Lett. 42 2001 5275 5278
82. W.-M. Dai, L.-P. Sun, and D.-S. Guo Tetrahedron Lett. 43 2002 7699 7702
83. C. Koradin, W. Dohle, A.L. Rodriguez, B. Schmid, and P. Knochel Tetrahedron 59 2003 1571 1587
84. TBAF-catalyzed cyclization of 2-alkynylanilines, see: A. Yasuhara, Y. Kanamori, M. Kaneko, A. Numata, Y. Kondo, and T. Sakamoto J. Chem. Soc., Perkin Trans. 1 1999 529 534
85. TMG-catalyzed cyclization of 2-alkynylanilines, see: (a) M. Botta, V. Summa, F. Corelli, G.D. Pietro, and P. Lombardi Tetrahedron: Asymmetry 7 1996 1263 1266
86. M.C. Fagnola, I. Candiani, G. Visentin, W. Cabri, F. Zarini, N. Mongelli, and A. Bedeschi Tetrahedron Lett. 38 1997 2307 2310
87. 4-promoted cyclization of 2-alkynylanilines, see: J. Barluenga, M. Trincado, E. Rubio, and J.M. González Angew. Chem. Int. Ed. 42 2003 2406 2409
88. For a recent review, see: G. Battistuzzi, S. Cacchi, and G. Fabrizi Eur. J. Org. Chem. 2002 2671 2681
89. A. Arcadi, S. Cacchi, and F. Marinelli Tetrahedron Lett. 33 1992 3915 3918
90. A. Arcadi, S. Cacchi, V. Carnicelli, and F. Marinelli Tetrahedron 50 1994 437 452
91. S. Cacchi, G. Fabrizi, F. Marinelli, L. Moro, and P. Pace Synlett 1997 1363 1370
92. M.D. Collini, and J.W. Ellingboe Tetrahedron Lett. 38 1997 7963 7966
93. S. Cacchi, G. Fabrizi, and P. Pace J. Org. Chem. 63 1998 1001 1011
94. S. Cacchi, G. Fabrizi, P. Pace, and F. Marinelli Synlett 1999 620 622
95. A. Arcadi, S. Cacci, G. Fabrizi, and F. Marinelli Synlett 2000 394 396
96. A. Arcadi, S. Cacchi, A. Cassetta, G. Fabrizi, and L.M. Parisi Synlett 2001 1605 1607
97. G. Battistuzzi, S. Cacchi, G. Fabrizi, F. Marinelli, and L.M. Parisi Org. Lett. 4 2002 1355 1358
98. S. Cacchi, G. Fabrizi, D. Lamba, F. Marinelli, and L.M. Parisi Synthesis 2003 728 734
99. R.C. Larock, and E.K. Yum J. Am. Chem. Soc. 113 1991 6689 6690
100. R.C. Larock, E.K. Yum, M.J. Doty, and K.K. Sham J. Org. Chem. 60 1995 3270 3271
101. K.R. Roesch, and R.C. Larock J. Org. Chem. 63 1998 5306 5307
102. R.C. Larock, E.K. Yum, and M.D. Refvik J. Org. Chem. 63 1998 7652 7662
103. R.C. Larock, M.J. Doty, and X. Han Tetrahedron Lett. 39 1998 5143 5146
104. K.R. Roesch, and R.C. Larock Org. Lett. 1 1999 1551 1553
105. K.R. Roesch, and R.C. Larock J. Org. Chem. 66 2001 412 420
106. H. Zhang, and R.C. Larock Org. Lett. 3 2001 3083 3086
107. D. Wensbo, A. Eriksson, T. Jeschke, U. Annby, S. Gronowitz, and L.A. Cohen Tetrahedron Lett. 34 1993 2823 2826
108. T. Jeschke, D. Wensbo, U. Annby, and S. Gronowitz Tetrahedron Lett. 34 1993 6471 6474
109. F. Maassarani, M. Pfeffer, J. Pencer, and E. Wehman J. Organomet. Chem. 466 1994 265 271
110. C.-y. Chen, D.R. Lieberman, R.D. Larsen, R.A. Reamer, T.R. Verhoeven, P.J. Reider, I.F. Cottrell, and P.G. Houghton Tetrahedron Lett. 35 1994 6981 6984
111. P. Blurton, A. Brickwood, and D. Dhanak Heterocycles 45 1997 2395 2405
112. A.L. Smith, G.I. Stevenson, C.J. Swain, and J.L. Castro Tetrahedron Lett. 39 1998 8317 8320
113. F. Ujjainwalla, and D. Warner Tetrahedron Lett. 39 1998 5355 5358
114. S.S. Park, J.-K. Choi, E.K. Yum, and D.-C. Ha Tetrahedron Lett. 39 1998 627 630
115. Synthesis on solid support, see: (q) H.-C. Zhang, K.K. Brumfield, and B.E. Maryanoff Tetrahedron Lett. 38 1997 2439 2442
116. J. Barluenga, J.M. González, M.A. García-Martín, P.J. Campos, and G. Asensio J. Org. Chem. 58 1993 2058 2060
117. 4, see: (b) W.-W. Sy Synth. Commun. 22 1992 3215 3219
118. Y. Wang, and T.-N. Huang Tetrahedron Lett. 39 1998 9605 9608
119. L.C. Cooper, G.G. Chicchi, K. Dinnell, J.M. Elliott, G.j. Hollingworth, M.M. Kurtz, K.L. Locker, D. Morrison, D.E. Shaw, K.-L. Tsao, A.P. Watt, A.R. Williams, and C.J. Swain Bioorg. Med. Chem. Lett. 11 2001 1233 1236
120. X.F. Lin, C. Ma, Y.W. Yang, and Y.G. Wang Chin. Chem. Lett. 13 2002 705 707 Also see Ref. 26q
121. W.-M. Dai, Y.K. Cheung, K.W. Tang, P.Y. Choi, and S.L. Chune Tetrahedron 51 1995 12263 12276
122. Solid-phase version of the heteroannulation toward nitroindoles was reported, see Refs. 15p and 20k.
123. X. Huang, Q.-F. Zhang, and H.H.Y. Sung Acta Crystallogr. E60 2004 o409 o410