Mild and efficient synthesis of benzoxazoles, benzothiazoles, benzimidazoles, and oxazolo[4,5-b]pyridines catalyzed by Bi(III) salts under solvent-free conditions

Monatshefte fur Chemie

Volumn 138, Issue 7, 2007, Pages 663-667

  Mohammadpoor Baltork, Iraj ^a   Khosropour, Ahmad R ^a   Hojati, Seyedeh F ^a  

^a UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

Benzimidazoles; Benzothiazoles; Benzoxazoles; Bi(III) salts; Oxazolo 4,5 b pyridines

Indexed keywords

EID: 34250769543     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-007-0655-9     Document Type: Article

References (87)

1. a) Denny WA, Rewcastle GW, Baguley B (1990) J Med Chem 33: 814;
2. b) Kondo J, Suzuki N, Imaoka T, Kawasaki T, Nakanishi A, Kawahara Y (1994) Anal Sci 10: 17;
3. c) Zhao M, Samoc M, Prasad PN, Reinhardt BA, Sinky M (1992) Chem Mater 2: 670;
4. d) Cassidy PE (1980) Thermally Stable Polymers, Marcel Dekker, New York;
5. e) Lin S, Yang L (2005) Tetrahedron Lett 46: 4315;
6. f) Mortimer CG, Wells G, Crochard J-P, Stone EL, Bradshaw TD, Stevens MFC, Westwell AD (2006) J Med Chem 49: 179;
7. g) Chen C, Chen Y-J (2004) Tetrahedron Lett 45: 113;
8. h) Frachy G; Crestini C, Berini R, Salidino R, Micione E (1994) Heterocycles 38: 2621
9. a) Kobayashi J, Madono T, Shigemori H (1995) Tetrahedron Lett 36: 5589;
10. b) Rodriguez AD, Ramirez C, Rodriguez II, Gonzales E (1999) Org Lett 1: 527;
11. c) Rodriguez II, Rodriguez AD (2003) J Nat Prod 66: 855;
12. d) Ueki M, Ueno K, Miyadoh S, Abe K, Shibata K, Taniguchi M, Oi S (1993) J Antibiot 46: 1089;
13. e) Paramashivappa R, Kumar PP, Subba Rao PV, Srinivasa Rao A (2003) Bioorg Med Chem Lett 13: 657;
14. f) Koči J, Klimešová V, Waisser K, Kaustová J, Dahse H-M, Möllmann U (2002) Bioorg Med Chem Lett 12: 3275;
15. g) Mann J, Baron A, Opoku-Boahen Y, Johansson E, Parkinson G, Kelland LR, Neidle S (2001) J Med Chem 44: 138;
16. h) Craigo WA, LeSueur BW, Skibo EB (1999) J Med Chem 42: 3324
17. Yildiz-Oren I, Yalcin I, Aki-Sener E, Ucarturk N (2004) Eur J Med Chem 39: 291
18. Song X, Vig BS, Lorenzi PL, Drach JC, Townsend LB, Amidon GL (2005) J Med Chem 48: 1274
19. Yamato M (1992) J Pharm Soc Jpn 112: 81
20. a) Kumar D, Jacob MR, Reynolds MB, Kerwin SM (2002) Bioorg Med Chem 10: 3997;
21. b) DeLuca MR, Kerwin SM (1997) Tetrahedron Lett 38: 199;
22. c) Sato S, Kajiura T, Noguchi M, Takehana K, Kobayasho T, Tsuji T (2001) J Antibiot 54: 102;
23. d) Ueki M, Shibata K, Taniguchi M (1998) J Antibiot 51: 883
24. Evans DA, Sacks CE, Kleschick WA, Taber TR (1979) J Am Chem Soc 101: 6789
25. [81 a) Bywater WG, Coleman WR, Kamm O, Merritt HH (1945) J Am Chem Soc 67: 905;
26. b) Benazzouz A, Boraud T, Dubédat P, Boireau A, Stutzmann J-M, Gross C (1995) Eur J Pharmacol 284: 299
27. a) Grimmett MR (1996) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive Heterocyclic Chemistry II, vol. 3, Elsevier Science Ltd, Oxford;
28. b) Grimmett MR (1997) Imidazole and Benzimidazole Synthesis, Academic Press, San Diego
29. Figge A, Altenbach HJ, Brauer DJ, Tielmann P (2002) Tetrahedron: Asymmetry 13: 137
30. a) Alcalde E, Dinarés I, Pérez-García L, Roca T (1992) Synthesis 395;
31. b) So Y-H, Heeschen JP (1997) J Org Chem 62: 3552;
32. c) Heuser S, Keenan M, Weichert AG (2005) Tetrahedron Lett 46: 9001
33. a) Pottorf RS, Chadha NK, Katkevics M, Ozola V, Suna E, Ghane H, Regberg T, Player MR (2003) Tetrahedron Lett 44: 175;
34. b) Nadaf RN, Siddiqui SA, Daniel T, Lahoti RJ, Srinivasan KV (2004) J Mol Catal A: Chem 214: 155
35. Hein DW, Alheim RJ, Leavitt JJ (1957) J Am Chem Soc 79: 427
36. a) Villemin D, Hammadi M, Martin B (1996) Synth Commun 26: 2895;
37. b) Doise M, Dennin F, Blondeau D, Sliwa H (1990) Tetrahedron Lett 31: 1155;
38. c) Jenkins GL, Knevel AM, Davis CS (1961) J Org Chem 26: 274
39. Terashima M, Ishii M (1982) Synthesis 484
40. a) Chakraborti AK, Rudrawar S, Kaur G, Sharma L (2004) Synlett 1533;
41. b) Dolbier Jr WR, Burkholder CR, Médebielle M (1999) J Fluorine Chem 95: 127
42. a) Hari A, Karan C, Rodrigues WC, Miller BL (2001) J Org Chem 66: 991;
43. b) Beaulieu PL, Haché B, Von Moos E (2003) Synthesis 1683;
44. c) Curini M, Epifano F, Montanari F, Rosati O, Taccone S (2004) Synlett 1832;
45. d) Gogoi P, Konwar D (2006) Tetrahedron Lett 47: 79;
46. e) Trivedi R, De SK, Gibbs RA (2006) J Mol Catal A: Chem 245: 8;
47. f) Navarrete-Vázquez G, Moreno-Diaz H, Aguirre-Crespo F, Leon-Rivera I, Villalobos-Molina R, Muñoz-Muñiz O, Estrada-Soto S (2006) Bioorg Med Chem Lett 16: 4169;
48. g) Lee CL, Lam Y, Lee S-Y (2001) Tetrahedron Lett 42: 109
49. Boyd GV (1984) In: Katritzky AR, Rees CW, Potts KT (eds) Comprehensive Heterocyclic Chemistry, Pergamon Press, New York, pp 177
50. Bu X-Z, Huang Z-S, Zhang M, Ma L, Xiao G-W, Gu L-Q (2001) Tetrahedron Lett 42: 5737
51. Bhawal BM, Mayabhate SP, Likhite AP, Deshmukh ARAS (1995) Synth Commun 25: 3315
52. Chen Y, Zeng DX (2004) J Org Chem 69: 5037
53. a) Suzuki H, Ikegami T, Matano Y (1997) Synthesis 249;
54. b) Reglinski J (1998) In: Norman NC (ed) Chemistry of Arsenic, Antimony and Bismuth, Balackie Academic and Professional, New York;
55. c) Anderson AM, Blazek JM, Garg P, Payne BJ, Mohan RS (2000) Tetrahedron Lett 41: 1527;
56. d) Leonard NM, Wieland LC, Mohan RS (2002) Tetrahedron 58: 8373;
57. e) Chakraborti AK, Shivani GR (2003) Synlett 1805;
58. f) Sabitha G, Venkata Reddy E, Swapna R, Mallikarjun Reddy N, Yadav JS (2004) Synlett 1276;
59. g) Yadav JS, Reddy BVS, Premalatha K (2004) Synlett 963;
60. h) Gosh R, Maiti S, Chakraborty A (2005) Synlett 115;
61. i) Sreedhar B, Swapna V, Sridhar C (2005) Catal Commun 6: 293;
62. j) Ollevier T, Mwene-Mbeja TM (2006) Tetrahedron Lett 47: 4051;
63. k) Fu H, Zhang L, Yao W, Zhu Y (2006) Appl Catal B: Env 66: 100;
64. l) Van Well WJM, Le MT, Schiødt NC, Hoste S, Stoltze P (2006) J Mol Catal A: Chem 256: 1;
65. m) Sparks DE, Patterson PM, Jacobs G, Dogimont N, Tackett A, Crocker M (2006) Appl Catal B: Env 65: 44
66. a) Irving Sax N, Lewis RJ (1988) Dangerous Properties of Industrial Materials, Van Nostrand Reinhold, New York, p 522;
67. b) Wormser U, Nir I (1994) In: Patai S (ed) The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds, Wiley, New York, p 715
68. a) Firouzabadi H, Mohammadpoor-Baltork I, Kolagar S (2001) Synth Commun 31: 905;
69. b) Mohammadpoor-Baltork I, Khosropour AR (2001) Molecules 996;
70. c) Mohammadpoor-Baltork I, Khosropour AR, Aliyan H (2001) Synth Commun 31: 3411;
71. d) Mohammadpoor-Baltork I, Khosropour AR, Aliyan H (2001) J Chem Res (S) 280;
72. e) Mohammadpoor-Baltork I, Aliyan H, Khosropour AR (2001) Tetrahedron 57: 5851;
73. f) Mohammadpoor-Baltork I, Khosropour AR (2002) Monatsh Chem 133: 189;
74. g) Mohammadpoor-Baltork I, Kharamesh B, Kolagar S (2002) Synth Commun 32: 1633;
75. h) Mohammadpoor-Baltork I, Khodaei MM, Nikoofar K (2003) Tetrahedron Lett 44: 591;
76. i) Mohammadpoor-Baltork I, Khosropour AR, Hojati SF (2005) Synlett 2747;
77. j) Khosropour AR, Mohammadpoor-Baltork I, Ghorbankhani H (2006) Catal Commun 7: 713;
78. k) Khosropour AR, Mohammadpoor-Baltork I, Ghorbankhani H (2006) Tetrahedron Lett 47: 3561;
79. l) Mohammadpoor-Baltork I, Memarian HR, Khosropour AR, Nikoofar K (2006) Heterocycles 68: 1837
80. a) Sam J, Plampin JN (1964) J Pharm Sci 53: 538;
81. b) Roussos M, Lecomte J (1962) Ger 1 124: 499, (1963)
82. Chem Abstr 57: 9858g;
83. c) Raban M, Chang H, Craine L, Hortelano E (1985) J Org Chem 50: 2205;
84. d) Wang H, Partch RE, Li Y (1997) J Org Chem 62: 5222;
85. e) Aldrich Catalogue Handbook of Fine Chemicals (2000-2001);
86. f) Kato H, Shiba T, Kitajima E, Kiyosawa T (1976) J Chem Soc Perkin Trans 1863;
87. g) Takahashi T, Yoneda F (1957) Pharm Bull 5: 350