Microwave-assisted, solvent-free Bischler indole synthesis

Synlett

Volumn , Issue 1, 2006, Pages 91-95

  Sridharan, Vellaisamy ^a   Perumal, Subbu ^a,b   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

Aniline monoalkylation; Indole synthesis; Microwave assisted synthesis; Solvent free synthesis

Indexed keywords

4 BROMOPHENACYL BROMIDE; ANILINE DERIVATIVE; BICARBONATE; INDOLE;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; MICROWAVE RADIATION; SOLID STATE; SYNTHESIS;

EID: 30544449717     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922760     Document Type: Article

References (80)

1. Tanaka, K. Solvent-Free Organic Synthesis; Wiley: New York, 2003.
2. For reviews of indole-related natural products, see: (a) Somei, M.; Yamada, F. Nat. Prod. Rep. 2003, 30, 216.
3. (b) Hibino, S.; Chosi, T. Nat. Prod. Rep. 2002, 19, 148.
4. (c) Hibino, S.; Chosi, T. Nat. Prod. Rep. 2001, 18, 66.
5. (d) Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 175.
6. For a summary of the applications of indoles, see: Gribble, G. W. Five-membered rings with one heteroatom and fused carbocyclic derivatives, In Comprehensive Heterocyclic Chemistry, 2nd ed., Vol. 2; Bird, C. W.; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1995, 207.
7. For recent reviews on indole synthesis, see: (a) Tois, T.; Franzén, R.; Koskinen, A. Tetrahedron 2003, 59, 5395.
8. (b) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
9. For summaries of these methods, see: (a) Brown, R. K. Indoles, Part 1; Houlighan, W. J., Ed.; Wiley-Interscience: New York, 1972, Chap. 2.
10. (b) Sundberg, R. G. Pyrroles and their Benzo Derivatives, In Comprehensive Heterocyclic Chemistry, Vol. 4; Bird, C. W.; Cheeseman, G. W. H.; Katrizky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, 313.
11. (c) Sundberg, R. J. Indoles; Academic Press: New York, 1996.
12. (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. M. Tetrahedron Lett. 1985, 26, 5963.
13. (b) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856.
14. (c) Ezquerra, J.; Pedregal, C.; Lamas, C.; Barluenga, J.; Pérez, M.; García-Martín, M. A.; González, J. M. J. Org. Chem. 1996, 61, 5804.
15. (d) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 61, 5804.
16. (e) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507.
17. (f) Dai, W.-M.; Guo, D.-S.; Sun, L.-P. Tetrahedron Lett. 2001, 42, 5275.
18. For reviews of palladium-catalyzed cyclization reactions, see: (a) Larock, R. C. J. Organomet. Chem. 1999, 576, 111.
19. (b) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry. A Guide for the Synthetic Chemist; Pergamon Press: Oxford, 2000.
20. (c) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Heterocycles 2002, 58, 667.
21. (a) Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289.
22. (b) Yu, M. S.; Leon, L. L.; McGuire, M. A.; Botha, G. Tetrahedron Lett. 1998, 39, 9347.
23. (c) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
24. (d) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529; and references therein from the same group.
25. (e) Esseveldt, B. C. J.; Delft, F. L.; Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717.
26. (f) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764.
27. Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126.
28. Arcadi, A.; Bianchi, G.; Marinelli, F. Synthesis 2004, 610.
29. (a) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507; and references therein from the same group.
30. (b) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571; and references therein from the same group.
31. (a) Yasuhara, A.; Kanimori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529.
32. (b) Botta, M.; Summa, V.; Corelli, F.; Pietro, G. D.; Lombardi, P. Tetrahedron: Asymmetry 1996, 7, 1263.
33. (c) Fagnola, M. C.; Candidiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307.
34. Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 2919.
35. (a) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305.
36. (b) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307.
37. (c) Zhang, H. C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89.
38. (d) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827.
39. (e) Barluenga, J.; Tricado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem. Int. Ed. 2003, 42, 2406.
40. (f) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 7342.
41. (g) Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539.
42. (h) Hong, K. B.; Lee, C. W.; Yum, E. K. Tetrahedron Lett. 2004, 45, 693.
43. (a) Gassman, P. G.; Van Bergen, T. J.; Gilbert, D. P.; Cue, B. W. J. Am. Chem. Soc. 1974, 96, 5495.
44. (b) Gassman, P. G.; Van Bergen, T. J. Org. Synth. Coll. Vol. 6; Wiley: New York, 1988, 601.
45. For a review, see: Dalpozzo, R.; Bartoli, G. Curr. Org. Chem. 2005, 9, 163.
46. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
47. (a) For an example using protic acids, see: Black, D. S. C.; Bowyer, M. C.; Bowyer, P. K.; Ivory, A. J.; Kim, M.; Kumar, N.; McConnell, D. B.; Popiolek, M. Aust. J. Chem. 1994, 47, 1741.
48. (b) For an example using Lewis acids or acidic resins, see: Bashford, K. E.; Cooper, A. L.; Kane, P. D.; Moody, C. J.; Muthusamy, S.; Swann, E. J. Chem. Soc., Perkin Trans. 1 2002, 1672.
49. Pchalek, K.; Jones, A. W.; Wekking, M. M. T.; Black, D. S. C. Tetrahedron 2005, 61, 77.
50. (a) Nordlander, J. E.; Catalane, D. B.; Kotian, K. D.; Stevens, R. M.; Haky, J. E. J. Org. Chem. 1981, 46, 778.
51. (b) Sundberg, R. J.; Laurino, J. P. J. Org. Chem. 1984, 49, 249.
52. Buu-Hoi, N. P.; Saint-Duf, G.; Deschamps, R.; Bigot, P.; Hieu, H.-T. J. Chem. Soc. C 1971, 2606.
53. (a) Black, D. S. C.; Gatehouse, B. M. K. C.; Théobald, F.; Wong, L. C. H. Aust. J. Chem. 1980, 33, 343.
54. (b) Black, D. S. C.; Kumar, N.; Wong, L. C. H. Aust. J. Chem. 1986, 39, 15.
55. For representative reviews and books on microwave-assisted organic synthesis, see: (a) Caddick, S. Tetrahedron 1995, 38, 10403.
56. (b) de la Hoz, A.; Díaz-Ortiz, A.; Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 22, 3659.
57. (c) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
58. (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
59. (e) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251.
60. (f) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2002.
61. (g) Varma, R. S. Advances in Green Chemistry: Chemical Synthesis Using Microwave Irradiation, AstraZeneca Research Foundation: India, 2002.
62. (h) Hayes, B. L. Aldrichimica Acta 2004, 37, 66.
63. (i) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.
64. (j) Tierney, J.; Lindstrom, P. Microwave Assisted Organic Synthesis; Blackwell: London, 2005.
65. (a) Pérez, R.; Pérez, E.; Suárez, M.; González, L.; Loupy, A.; Jimeno, M. L.; Ochoa, C. Org. Prep. Proced. Int. 1997, 29, 671.
66. (b) Limousin, C.; Cleophax, J.; Loupy, A.; Petit, A. Tetrahedron 1998, 54, 13567.
67. (c) Dandia, A.; Arya, K.; Khaturia, S.; Yadav, P. ARKIVOC 2005, (xii), 80.
68. 13C NMR spectra, and melting points very similar to those previously described (Table 1).
69. (b) Cowper, R. M.; Davidson, L. H. Org. Synth. Coll. Vol. 2; Wiley: New York, 1962, 480.
70. (a) Bischler, A.; Brion, H. Ber. Dtsch. Chem. Ges. 1892, 25, 2860.
71. (b) Bischler, A.; Firemann, P. Ber. Dtsch. Chem. Ges. 1893, 26, 1336.
72. Blades, C. E.; Wilds, A. L. J. Org. Chem. 1956, 21, 1013.
73. Smith, A. B.; Visnick, M.; Haseltine, J. N.; Sprengeler, P. A. Tetrahedron 1986, 42, 2957.
74. Hudkins, R. L.; Diebold, J. L.; Marsh, F. D. J. Org. Chem. 1995, 60, 6218.
75. Junjappa, H. Synthesis 1975, 798.
76. Brown, F.; Mann, F. G. J. Chem. Soc. 1948, 847.
77. Crowther, A. F.; Mann, F. G.; Purdie, D. J. Chem, Soc. 1943, 58.
78. Macleod C., McKiernan G. J., Guthrie E. J., Farrugia L. J., Hamprecht D. W., Macritchie J., Hartley R. C.; J. Org. Chem.; 2003, 68: 387.
79. Black, D. S. C.; Kumar, N.; McCornell, D. B. Tetrahedron 2001, 57, 2203.
80. General Procedure for the One-Pot Synthesis of 2-Arylindoles from Phenacyl Bromides and Anilines under Microwave Irradiation. Phenacyl bromide (1 mmol) was stirred with aniline (2 mmol) at r.t. without any base to neutralize the liberated HBr. The mixture was kept at r.t. with occasional stirring for 3 h. To the solid mixture, containing N-phenacyl aniline and anilinium hydrobromide, was added 3-4 drops of DMF and the mixture was irradiated in a microwave oven at 600 W for 1 min. After completion of the reaction, the mixture was treated as described for the two-step method to give the pure 2-arylindoles.