Synthesis of novel substituted phenanthrenes and polycyclic heteroarenes by Pd-catalyzed, direct, intramolecular arylation/heteroarylation

European Journal of Organic Chemistry

Volumn , Issue 2, 2010, Pages 338-344

  Yadav, Ashok K ^a   Ila, Hiriyakkanavar ^a   Junjappa, Hiriyakkanavar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Cyclization; Heteroarenes; Palladium; Phenanthrenes; Polycycles

Indexed keywords

EID: 73349136726     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901036     Document Type: Article

References (86)

1. a) A. Iuliano, P. Piccioli, D. Fabbri, Org. Lett. 2004, 6, 3711-3714 and references cited therein;
2. b) E. R. Walker, S. Y. Leung, A. G. M. Barrett, Tetrahedron Lett. 2005, 46, 6537-6540 and references cited therein;
3. c) T. R. Kelly, Q. Li, V. Bhushan, Tetrahedron Lett. 1990, 31, 161-164;
4. d) R. X.-F. Ren, N. C. Chaudhuri, P. L. Paris, S. I. V. Rumney, E. T. Kool, J. Am, Chem. Soc. 1996, 118, 7671-7678;
5. e) S. Kumar, J. Org. Chem, 1997, 62, 8535-8539;
6. f) C. B. de Koning, J. P. Michael, A. L. Rousseau, Tetrahedron Lett. 1998, 39, 8725-8728;
7. g) S. Radix, R. Barret, Tetrahedron 2007, 63, 12379-12387.
8. Review: a) G. M. Cragg, D. J. Newman, J. Nat. Product 2004, 67, 232-244;
9. b) V. Mamane, P. Hannen, A. Fuerstner, Chem. Eur. J. 2004, 10, 4556-4575.
10. a) K. Takimiya, Y. Konda, H. Ebata, N. Niihara, T. Otsubo, J. Org. Chem. 2005, 70, 10569-10571;
11. b) S.-M. Yang, J.-J. Shie, J.-M. Fang, S. K. Nandy, H.-Y. Chang, S.-H. Lu, G. Wang, J. Org. Chem. 2002, 67, 5208-5215 and references cited therein;
12. c) Y. Kono, H. Miyamoto, Y. Aso, T. Otsubo, F. Ogura, T. Tanaka, M. Sawada, Angew. Chem. Int. Ed. Engl. 1989, 28, 1222-1224 and references cited therein;
13. d) J. Roncali, Chem. Rev. 1997, 97, 173-205;
14. e) K. Takimiya,Y. Kunugi, Y. Toyoshima, T. Otsubo, J. Am. Chem, Soc. 2005, 127, 3605-3612;
15. f) Y. Nicolas, P. Blanchard, J. Roncali, M. Allain, N. Mercier, A.-L. Deman, J. Tardy, Org. Lett. 2005, 7, 3513-3516 and references cited therein.
16. a) K. Kobayashi, C. L. Gajurel, J. Chem. Soc. Chem. Commun. 1986, 1779-1780;
17. b) S. Yoshida, M. Fujii, Y. Aso, T. Otsubo, F. Ogura, J. Org. Chem. 1994, 59, 3077-3081.
18. K. Starcevic, M. Kralj, I. Piantanida, L. Suman, K. Pavelic, G. Karminski-Zamola, Eur. J. Med. Chem. 2006, 41, 925-939.
19. W. D. Wilson, Y. H. Wang, S. Kusuma, S. Chandrasekaran, N. C. Yang, D. W. Boykin, J. Am. Chem. Soc. 1985, 107, 4989-4995.
20. Reviews: a) H.-J. Knoelker, K. R. Reddy, Chem. Rev. 2002, 102, 4303-4427;
21. b) J. Leonard, Nat. Prod. Rep. 1999, 16, 319-338.
22. a) M. Rogge, G. Fischer, U. Pindur, D. Schollmeyer, Monatsh. Chem. 1996, 127, 97-102;
23. b) S. Routier, G. Coudert, J.-Y. Merour, Tetrahedron Lett. 2001, 42, 7025-7080;
24. c) C. Bailly, X. Qu, J. B. Chaires, P. Colson, C. Houssier, M. Ohkubo, S. Nishimura, T. Yoshinari, J. Med. Chem. 1999, 42, 2927-2935.
25. Synthesis: a) C. Sanchez-Martinez, M. M. Faul, C. Shih, K. A. Sullivan, J. L. Grutsch, J. T. Cooper, S. P. Kolis, J. Org. Chem. 2003, 68, 8008-8014;
26. b) R. Pathak, J. M. Nhlapo, S. Govender, J. P. Michael, W. A. L. van Otterlo, C. B. de Koning, Tetrahedron 2006, 62, 2820-2830;
27. c) C. B. de Koning, J. P. Michael, J. M. Nhlapo, R. Pathak, W. A. L. van Otterlo, Synlett 2003, 705-707;
28. d) X. Cai, V. Snieckus, Org. Lett. 2004, 6, 2293-2295.
29. D. J. Carini, R. F. Kaltenbach, J. Liu, P. A. Benfield, J. Boylan, M. Boisclair, L. Brizuela, C. R. Burton, S. Cox, R. Grafstrom, B. A. Harrison, K. Harrison, E. Akamike, J. A. Markwalder, Y. Nakano, S. P. Seitz, D. M. Sharp, G. L. Trainor, T. M. Sielecki, Bioorg. Med. Chem. Lett. 2001, 11, 2209-2211.
30. a) E. Piers, R. Britton, R. J. Andersen, J. Org. Chem. 2000, 65, 530-535;
31. b) J. Bergman, E. Desarbre, E. Koch, Tetrahedron 1999, 55, 2363-2370;
32. c) S. Routier, P. Peixoto, J.-Y. Merour, G. Coudert, N. Dias, C. Bailly, A. Pierre, S. Leonce, D.-H. Caignard, J. Med. Chem. 2005, 48, 1401-1413.
33. a) H. Bregman, D. S. Williams, G. E. Atilla, P. J. Carroll, E. Meggers, J. Am, Chem. Soc. 2004, 126, 13594-13595;
34. b) C. B.de Koning, J. P. Michael, A. L. Rousseau, J. Chem. Soc. Perkin Trans. 1 2000, 1705-1713.
35. Reviews: a) W. Froehner, M. P. Krahl, K. R. Reddy, H. J. Knoelker, Heterocycles 2004, 63, 2393-2407;
36. b) H. Hagiwara, T. Choshi, J. Nobuhiro, H. Fujimoto, S. Hibino, Chem. Pharm. Bull. 2001, 49, 881-886;
37. c) S. C. Pelly, C. J. Parkinson, W. A. L. van Otterlo, C. B. de Koning, J. Org. Chem. 2005, 70, 10474-10481 and references cited therein.
38. Review: U. Pindur, Y.-S. Kim, F. Mehrabani, Curr. Med. Chem. 1999, 6, 29-69.
39. a) C. Sanchez-Martinez, C. Shih, G. Zhu, T. Li, H. B. Brooks, B. K. R. Patel, R. M. Schultz, T. B. De Hahn, C. D. Spencer, S. A. Watkins, C. A. Ogg, E. Considine, J. A. Dempsey, F. Zhang, Bioorg. Med. Chem. Lett. 2003, 13, 3841-3846;
40. b) L. J. Wilson, C. Yang, W. V. Murray, Tetrahedron Lett. 2007, 48, 7399-7403.
41. M. M. Faul, T. A. Engler, K. A. Sullivan, J. L. Grutsch, M. T. Clayton, M. J. Martinelli, J. M. Pawlak, M. Le Tourneau, D. S. Coffey, S. W. Pedersen, S. P. Kolis, K. Furness, S. Malhotra, R. S. Al-Awar, J. E. Ray, J. Org. Chem, 2004, 69, 2967-2975 and references cited therein.
42. Review: G. Bringmann, R. Walter, R. Weirich, Angew. Chem. Int. Ed. Engl 1990, 29, 977-991.
43. a) I. Moreno, I. Tellitu, E. Dominguez, R. San Martin, Eur. J. Org. Chem. 2002, 2126-2135 and references cited therein;
44. b) R. Olivera, R. SanMartin, E. Dominguez, J. Org. Chem. 2000, 65, 7010-7019 and references cited therein;
45. c) R. Olivera, R. SanMartin, E. Dominguez, Synlett 2000, 1028-1030.
46. Recent papers: a) K. Hamza, R. Abu-Reziq, D. Avnir, J. Blum, Org. Lett. 2004, 6, 925-927;
47. b) K. Hamza, J. Blum, Tetrahedron. Lett. 2007, 48, 293-295;
48. c) J. F. Almeida, L. Castedo, D. Fernandez, A. G. Neo, V. Romero, G. Tojo, Org. Lett. 2003, 5, 4939-4941;
49. d) E. M. Beccalli, A. Marchesini, T. Pilati, Tetrahedron 1993, 49, 4741-4758;
50. e) S. Samori, M. Hara, T.-I. Ho, S. Tojo, K. Kawai, M. Endo, M. Fujitsuka, T. Majima, J. Org. Chem. 2005, 70, 2708-2712.
51. a) M. Shimizu, K. Mochida, T. Hiyama, Angew. Chem, Int. Ed. 2008, 47, 9760-9764;
52. b) Y. H. Kim, H. Lee, Y. J. Kim, B. T. Kim, J.-N. Heo, J. Org. Chem, 2008, 73, 495-501.
53. K. Wang, M. Lu, A. Yu, X. Zhu, Q. Wang, J. Org. Chem. 2009, 74, 935-938 and references therein.
54. Radical-mediated biaryl coupling: a) D. C. Harrowven, M. I. T. Nunn, D. R. Fenwick, Tetrahedron. Lett. 2002, 43, 3185-3187;
55. b) S. R. Flanagan, D. C. Harrowven, M. Bradley, Tetrahedron Lett. 2003, 44, 1795-1798;
56. c) C. Hoarau, A. Couture, E. Deniau, P. Grandclaudon, Synthesis 2001, 1462-1470.
57. Reviews: a) H. Ila, H. Junjappa, P. K. Mohanta in Progress in Heterocyclic Chemistry (Eds.: G. W. Gribble, T. L. Gilchrist), Pergamon Press, Oxford, 2001, vol.13, chapter 1, pp. 1-24;
58. b) H. Junjappa, H. Ila, C. V Asokan, Tetrahedron 1990, 46, 5423-5506;
59. c) H. Ila, H. Junjappa, O. Barun, J. Organomet. Chem. 2001, 624, 34-40.
60. Recent papers: a) N. C. Misra, K. Panda, H. Ila, H. Junjappa, J. Org. Chem. 2007, 72, 1246-1251;
61. b) G. S. M. Sundaram, B. Singh, C. Venkatesh, H. Ila, H. Junjappa, J. Org. Chem. 2007, 72, 5020-5023;
62. c) C. Venkatesh, G. S. M. Sundaram, H. Ha, H. Junjappa, J. Org. Chem. 2006, 77, 1280-1283;
63. d) C. Venkatesh, B. Singh, P. K. Mahata, H. Ila, H. Junjappa, Org. Lett. 2005, 7, 2169-2172;
64. e) K. Panda, C. Venkatesh, H. Ila, H. Junjappa, E. J. Org. Chem. 2005, 2045-2063;
65. f) S. Peruncheralathan, T. A. Khan, H. Ila, H. Junjappa, J. Org. Chem. 2005, 70, 10030-10035;
66. g) S. Peruncheralathan, A. K. Yadav, H. Ila, H. Junjappa, J. Org. Chem. 2005, 70, 9644-9647;
67. h) G. S. M. Sundaram, C. Venkatesh, U. K. Syam Kumr, H. Ha, H. Junjappa, J. Org. Chem. 2004, 69, 5760-5762;
68. i) S. Peruncheralathan, T. A. Khan, H. Ila, H. Junjappa, Tetrahedron 2004, 60, 3457-3464;
69. j) P. K. Mahata, C. Venkatesh, U. K. Syam Kumar, H. Ila, H. Junjappa, J. Org. Chem. 2003, 68, 3966-3975;
70. k) K. Panda, J. R. Suresh, H. lia, H. Junjappa, J. Org. Chem. 2003, 68, 3498-3505.
71. S. Kumar, S. Peruncheralathan, H. lia, H. Junjappa, Org. Lett. 2008, 10, 965-968.
72. P. P. Singh, A. K. Yadav, H. Ila, H. Junjappa, J. Org. Chem. 2009, 74, 5496-5501.
73. 1H NMR signals for the SMe groups). Similarly, heating of pure (Z)-configured la under identical conditions caused the formation of some amount of the (E) isomer [(E)I(Z) = 1:15].
74. No trace of thieno-fused heterocycles such as 3o,p were isolated from the Pd-catalyzed cyclization.
75. a) A. M. Echavarren, B. Gomez-Lor, J. J. Gonzalez, O. de Frutos, Synlett 2003, 585-597;
76. b) B. Martin-Matute, C. Mateo, D. J. Cardenas, A. M. Echavarren, Chem. Eur. J. 2001, 7, 2341-2348.
77. For a detailed mechanism, see: a) L.-C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem, Soc. 2006, 128, 581-590 and references therein;
78. b) E. J. Hennessy, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 12084-12085 and references therein.
79. a) B. Sezen, D. Sames, J. Am. Chem, Soc. 2003, 125, 5274-5275;
80. b) B. Glover, K. A. Harvey, B. Liu, M. J. Sharp, M. F. Tymoschenko, Org. Lett. 2003, 5, 301-304;
81. c) B. S. Lane, M. A. Brown, D. Sames, J. Am. Chem. Soc, 2005, 127, 8050-8057;
82. d) C. C. Hughes, D. Trauner, Angew. Chem. Int. Ed. 2002, 41, 1569-1572.
83. The 3-(2-furyl)acrylonitriles 1c and 1i undergo facile intramolecular arylation to give furo-fused heteroarenes 2c and 2i in good yields. However, in the case of 1o, geometrical and other factors also appear to intervene, resulting in the different course of reaction to give 3o instead of 2o.
84. X Spencer, M. Pfeffer, A. DeCian, J. Fischer, J. Org. Chem. 1995, 60, 1005-1012.
85. a) B. S. Furniss, A. X Hannaford, P. W. G. Smith, A. R. Tatachell, Vogel's Textbook of Practical Organic Chemistry, 5th ed., ELBS edition, 1989;
86. b) D. D. Perrin, W. L. F. Armarego, Puri fication of Laboratory Chemicals, 3rd ed., Pergamon Press, Oxford, 1988.