Synthesis of fused imidazoles and benzothiazoles from (hetero)aromatic ortho-diamines or ortho-aminothiophenol and aldehydes promoted by chlorotrimethylsilane

Synthesis

Volumn , Issue 21, 2006, Pages 3715-3726

  Ryabukhin, Sergey V ^a,b   Plaskon, Andrey S ^a,b   Volochnyuk, Dmitriy M ^a,c   Tolmachev, Andrey A ^b  

^a ENAMINE LTD   (Ukraine)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

Aldehydes; Benzimidazoles; Benzothiazoles; Chlorotrimethylsilane; Parallel synthesis

Indexed keywords

ALDEHYDES; AMINO ACIDS; OXIDATION; PARAFFINS; PHENOLS; SYNTHESIS (CHEMICAL);

BENZIMIDAZOLES; BENZOTHIAZOLES; CHLOROTRIMETHYLSILANE; PARALLEL SYNTHESIS;

AROMATIC COMPOUNDS;

2 AMINO 8 (4 METHOXYPHENYL) 1 METHYL 1,7 DIHYDRO 6H PURIN 6 ONE; 2 AMINOTHIOPHENOL; 2 {[(4 BROMOPHENYL)METHYLENE}AMINO} 4 METHYLPHENOL; 3 AMINO 4 (ETHYLAMINO) N,N DIMETHYLBENZENESULFONAMIDE; 4 FORMYL 1,5 DIMETHYLPYRROLE 2 CARBONITRILE; ALDEHYDE; BENZOTHIAZOLINE DERIVATIVE; CHLOROTRIMETHYLSILANE; DIAMINE; ETHYL 3 AMINO 4 (ETHYLAMINO)BENZOATE; IMIDAZOLE DERIVATIVE; N1 BENZYL 4 (TRIFLUOROMETHYL)BENZENE 1,2 DIAMINE; N1 BENZYL 4 CHLOROBENZENE 1,2 DIAMINE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33751368521     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950289     Document Type: Article

References (73)

1. (a) Spasov, A. A.; Yozhitsa, I. N.; Bugaeva, L. I.; Anisimiva, V. A. Pharm. Chem. J. 1999, 33, 232.
2. (b) Preston, P. N. In The Chemistry of Heterocyclic Compounds, Benzimidazoles and Congeneric Tricyclic Compounds, Part 2, Vol. 40; John Wiley and Sons: New York, 1980, Chap. 10.
3. (c) Preston, P. N. Chem. Rev. 1974, 74, 279.
4. For recent examples, see: (a) Buerli, R. W.; McMinn, D.; Kaizerman, J. A.; Hu, W.; Ge, Y.; Pack, Q.; Jiang, V.; Gross, M.; Garcia, M.; Tanaka, R.; Moser, H. E. Bioorg. Med. Chem. Lett. 2004, 14, 1253.
5. (b) Ryu, C.-K.; Song, E.-H.; Shim, J.-Y.; You, H.-J.; Choi, K. U.; Choi, I. H.; Lee, E. Y.; Chae, M. J. Bioorg. Med. Chem. Lett. 2003, 13, 17.
6. (c) Hranjec, M.; Grdisa, M.; Pavelic, K.; Boykin, D. W.; Karminski-Zamola, G. Farmaco 2003, 58, 1319.
7. (d) Tawar, U.; Jain, A. K.; Dwarakanath, B. S.; Chandra, R.; Singh, Y.; Chaudhury, N. K.; Khaitan, D.; Tandon, V. J. Med. Chem. 2003, 46, 3785.
8. (e) Guemues, F.; Demirci, A. B.; Oezden, T.; Eroglu, H.; Diril, N. Pharmazie 2003, 58, 303.
9. (f) Yang, D.; Fokas, D.; Li, J.; Yu, L.; Baldino, C. M. Synthesis 2005, 47.
10. For recent examples, see: (a) Beaulieu, P. L.; Haché, B.; von Moos, E. Synthesis 2003, 1683.
11. (b) Jung, M. H.; Park, J. M.; Lee, I.-Y. C.; Ahn, M. J. Heterocycl. Chem. 2003, 40, 37.
12. (c) Reddy, G. V.; Rao, V. V. V. N. S. R.; Narsaiah, B.; Rao, P. S. Synth. Commun. 2002, 32, 2467.
13. (d) Nagata, K.; Itoh, T.; Ishikawa, H.; Ohsawa, A. Heterocycles 2003, 61, 93.
14. (e) Ben-Alloum, A.; Bougrin, S.; Soufiaoui, M. Tetrahedron Lett. 2003, 44, 5935.
15. (a) Blettner, C. G.; König, W. A.; Rühter, G.; Stenzel, W.; Schotten, T. Synlett 1999, 307.
16. (b) Sun, Q.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. J. J. Med. Chem. 1995,38, 3638.
17. (c) Ben-Alloum, A.; Bakkas, S.; Soufiaoui, M. Tetrahedron Lett. 1998, 39, 4481.
18. (d) Satz, A. L.; Bruice, T. C. Bioorg. Med. Chem. Lett. 1999, 9, 3261.
19. (e) Rangarajan, M.; Kim, J. S.; Sim, S.-P.; Liu, A.; Liu, L. R.; LaVoie, E. J. Bioorg. Med. Chem. 2000, 8, 2591.
20. (f) Black, D. S. C.; Kumar, N.; Wong, L. C. H. Synthesis 1986, 474.
21. (a) Denny, W. A.; Rewcastle, G. W.; Baguley, B. C. J. Med. Chem. 1990, 33, 814.
22. (b) Dang, Q.; Brown, B. S.; Erion, M. D. Tetrahedron Lett. 2000, 41, 6559.
23. (c) Singh, M. P.; Sasmal, S.; Lu, W.; Chatterjee, M. N. Synthesis 2000, 1380.
24. (d) Gravatt, G. L.; Baguley, B. C.; Wilson, W. R.; Denny, W. A. J. Med. Chem. 1994, 37, 4338.
25. (e) Das, T. M.; Rao, C. P.; Kalle, N.; Rissanen, K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2003, 42, 661.
26. (a) Vanden Eynde, J. J.; Delfosse, F.; Lor, P.; Van Haverbeke, Y. Tetrahedron 1995, 51, 5813.
27. (b) Hopkins, K. T.; Wilson, W. D.; Bender, B. C.; McCurdy, D. R.; Hall, J. E.; Tidwell, R. R.; Kumar, A.; Bajic, M.; Boykin, D. W. J. Med. Chem. 1998, 41, 3872.
28. (c) Lombardy, R. L.; Tanious, F. A.; Ramachandran, K.; Tidwell, R. R.; Wilson, W. D. J. Med. Chem. 1996, 39, 1452.
29. (d) Starcevic, K.; Boykin, D. W.; Karminski-Zamola, G. Heterocycl. Commun. 2002, 8, 221.
30. Chikashita, H.; Nishida, S.; Miyazaki, M.; Morita, Y.; Itoh, K. Bull. Chem. Soc. Jpn. 1987, 60, 737.
31. Pätzold, F.; Zeuner, F.; Heyer, T. H.; Niclas, H.-J. Synth. Commun. 1992, 22, 281.
32. Risitano, F.; Grassi, G.; Foti, F.; Bilardo, C. Heterocycles 2001, 55, 1311.
33. (a) Ridley, H. F.; Spickett, R. G. W.; Timmis, G. M. J. Heterocycl. Chem. 1965, 2, 453.
34. (b) Göker, H.; Kus, C.; Boykin, D. W.; Yildiz, S.; Altanlar, N. Bioorg. Med. Chem. 2002, 10, 2589.
35. (c) Meric, A.; Incesu, Z.; Isikdag, I. Farmaco 2002, 57, 543.
36. Kawashita, Y.; Nakamichi, N.; Kawabata, H.; Hayashi, M. Org. Lett. 2003, 5, 3713.
37. 3SiCl as a condensation agent, see: (a) Ryabukhin, S. V.; Plaskon, A. S.; Tverdokhlebov, A. V.; Tolmachev, A. A. Synth. Commun. 2004, 34, 1483.
38. (b) Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synlett 2004, 2287.
39. (c) Zhu, Y.-L.; Huang, S.-L.; Pan, Y.-J. Eur. J. Org. Chem. 2005, 2354.
40. (d) Zhu, Y.-L.; Pan, Y.-J.; Huang, S.-L. Synth. Commun. 2004, 34, 3167.
41. (e) Heaney, H.; Papageorgeogu, G.; Wilkins, R. F. Tetrahedron 1997, 53, 2941.
42. 3Sil as a condensation agent, see: (f) Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S. Synthesis 2004, 263.
43. (g) Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. Synlett 2003, 858.
44. (h) Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2003, 44, 4129.
45. For recent examples of the synthesis of benzothiazoles starting from o-aminothiophenol and aldehydes, see: (a) Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Heterocycles 2004, 62, 197.
46. (b) Ben-Alloum, A.; Bakkas, S.; Soufiaoui, M. Tetrahedron Lett. 1997, 38, 6395.
47. For recent examples of the synthesis of benzoxazoles starting from o-aminophenoles and aldehydes, see ref. 11 and: Chang, J.; Zhao, K.; Pan, S. Tetrahedron Lett. 2002, 43, 951.
48. For recent examples of the synthesis of 3H-imidazo[4,5-b]pyridines from 2,3-diaminopyridines and aldehydes, see ref. 5c and: (a) Singh, A. K.; Lown, J. W. Synth. Commun. 2000, 30, 923.
49. (b) Oguchi, M.; Wada, K.; Honma, H.; Tanaka, A.; Kaneko, T.; Sakakibara, S.; Ohsumi, J.; Serizawa, N.; Fujiwara, T.; Horikoshi, H.; Fujita, T. J. Med. Chem. 2000, 43, 3052.
50. (c) Blettner, C. G.; Koenig, W. A.; Ruehter, G.; Stenzel, W.; Schotten, T. Synlett 1999, 307.
51. For examples of the synthesis of 2,6-diaminopurines starting from 2,4,5,6-tetraaminopyrimidine and aldehydes, see: Gangjee, A.; Vasudevan, A.; Queener, S. F. J. Med Chem. 1997, 40, 3032.
52. For recent examples of synthesis of xanthines from 5,6-diaminouracils and aldehydes, see: (a) De Araujo, A. D.; Bacher, E.; Demnitz, F. W. J.; Santos, D. A. Heterocycles 1999, 57, 29.
53. (b) Mueller, C. E.; Shi, D.; Manning, M. Jr.; Daly, J. W. J. Med. Chem. 1993, 36, 3341.
54. (c) Kuefner-Muehl, U.; Weber, K. H.; Walther, G.; Stransky, W.; Ensinger, H.; Schingnitz, G.; Kuhn, F. J.; Lehr, E. DE 03843117, 1991; Chem. Abstr. 1991, 114, 164265p.
55. 2, see: Liu, J.; Dang, Q.; Wei, Z.; Bai, X. J. Comb. Chem. 2005, 7, 627.
56. (a) Jahn, U.; Schroth, W. Tetrahedron Lett. 1993, 34, 5863.
57. (b) Schroth, W.; Jahn, U.; Stroehl, D. Chem. Ber. 1994, 127, 2013.
58. (a) Kalle, A.-G. DE 1137625,1958, Chem. Abstr. 1963, 59, 11515c.
59. (b) Bunnett, J.F.; Hrutfiord, B.F. J. Am. Chem. Soc. 1961, 83, 1691.
60. (c) Nagase, R.; Kawashima, T.; Yoshifuji, M. Heterocycles 1977, 8, 243.
61. (d) Cerniani, A.; Passerini, R. J. Chem. Soc. 1954, 2261.
62. (e) Anthony K., Brown R. G., Hepworth J. D., Hudson K. W., May B., West M. A.; J. Chem. Soc., Perkin Trans. 2; 1984, 2111.
63. (f) Cohen V, V. I. J. Heterocycl. Chem. 1979, 16, 13.
64. (g) Szczepankiewicz, B. G.; Rohde, J. J.; Kurukulasuriya, R. Org. Lett. 2005, 7, 1833.
65. (h) Dubey, P. K.; Kumar, R.; Vino, D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2000, 39, 746.
66. (a) Young, R. C.; Jones, M.; Milliner, K. J.; Rana, K. K.; Ward, J. G. J. Med. Chem. 1990, 33, 2073.
67. (b) Mueller, C. E.; Thorand, M.; Qurishi, R.; Diekmann, M.; Jacobson, K. A.; Padgett, W. L.; Daly, J. W. J. Med. Chem. 2002, 45, 3440.
68. Nicolai, E.; Goyard, J.; Benchetrit, T.; Teulon, J. M.; Caussade, F.; Virone, A.; Delchambre, C.; Cloarec, A. J. Med. Chem. 1993, 56, 1175.
69. Sato, K.; Kitaguchi, H.; Takechi, M.; Tsukase, M.; Kato, M. JP 182039, 1986; Chem. Abstr. 1987, 106, 147020x.
70. Curran, W. V.; Angier, R. B. J. Am. Chem. Soc. 1958, 80, 6095.
71. McClure, M. S.; Roschangar, F.; Hodson, S. J.; Millar, A.; Osterhout, M. H. Synthesis 2001, 1681.
72. Bebernitz, G. R.; Argentieri, G.; Battle, B.; Brennan, C.; Balkan, B.; Burkey, B. F.; Eckhardt, M.; Gao, J.; Kapa, P.; Stroehschein, R. J.; Schuster, H. F.; Wilson, M.; Xu, D. D. J. Med. Chem. 2001, 44, 2601.
73. Kristek, F.; Klicnar, J.; Vetersnik, P. Collect. Czech. Chem. Commun. 1971, 36, 3608.