Lawesson's reagent and microwaves: A new efficient access to benzoxazoles and benzothiazoles from carboxylic acids under solvent-free conditions

Synlett

Volumn , Issue 2, 2007, Pages 313-317

  Seijas, Julio A ^a   Vázquez Tato, M Pilar ^a   Carballido Reboredo, M Raquel ^a   Crecente Campo, José ^a   Romar López, Lucía ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Benzothiazoles; Benzoxazoles; Lawesson's reagent; Microwaves; Thiobenzoic acid

Indexed keywords

2 PHENYLBENZOTHIAZOLE; 2 PHENYLBENZOXAZOLE; 2,4 BIS(4 METHOXYPHENYL) 1,3,2,4 DITHIADIPHOSPHETANE 2,4 DISULFIDE; BENZOIC ACID DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; CARBOXYLIC ACID; DISULFIDE; THIOBENZOIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICROWAVE RADIATION; SYNTHESIS;

EID: 33847036694     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967994     Document Type: Article

References (64)

1. Pinar, A.; Yurdakul, P.; Yildiz, I.; Temiz-Arpaci, O.; Acan, N. L.; Aki-Sener, E.; Yalcin, I. Biochem. Biophys. Res. Commun. 2004, 317, 670.
2. Rida, S. M.; Ashour, F. A.; El-Hawash, S. A. M.; ElSemary, M. M.; Badr, M. H.; Shalaby, M. A. Eur. J. Med. Chem. 2005, 40, 949.
3. Sum, P.-E.; How, D.; Torres, N.; Newman, H.; Petersen, P. J.; Mansoura, T. S. Bioorg. Med. Chem. Lett. 2003, 13, 2607.
4. Mahran, M. A.; El-Nassry, S. M. F.; Allam, S. R.; El-Zawawy, L. A. Pharmazie 2003, 58, 527.
5. Sondhi, S. M.; Singh, N.; Kumar, A.; Lozach, O.; Meijer, L. Bioorg. Med. Chem. 2006, 14, 3758.
6. Sato, F.; Inoue, Y.; Omodani, T.; Imano, K.; Okazaki, H.; Takemura, T.; Komiya, M. Bioorg. Med. Chem. Lett. 2002, 12, 551.
7. Reiser, A.; Leyshon, L. J.; Saunders, D.; Mijovic, M. V.; Bright, A.; Bogie, J. J. Am. Chem. Soc. 1972, 94, 2414.
8. Ke, W. J.; Xu, H. S.; Liu, X. F.; Luo, X. H. Heterocycles 2000, 53, 1821.
9. Kelleher, K. A.; Stanhope, M. T. US 2002069453, 2002; Chem. Abstr. 2002, 137, 7475.
10. Song, K. C.; Kim, J. S.; Park, S. M.; Chung, K.-C.; Ahn, S.; Chang, S.-K. Org. Lett. 2006, 8, 3413.
11. Luan, X. H.; Cerqueira, N. M. F. S. A.; Oliveira, A. M. A. G.; Raposo, M. M. M.; Rodrigues, L. M. C. P.; Campos, A. M. F. O. Adv. Colour Sci. Tech. 2002, 5, 18.
12. Hoveyda, H. R.; Rettig, S. J.; Orvig, C. Inorg. Chem. 1993, 32, 4909.
13. Dolbier, W. R. Jr.; Burkholder, C. R.; Medebielle, M. J. Fluorine Chem. 1999, 95, 127.
14. So, Y.-H.; Heeschen, J. P. J. Org. Chem. 1997, 62, 3552.
15. Cohen, V. I. J. Heterocycl. Chem. 1979, 16, 13.
16. Kumar, R. V. Asian J. Chem. 2004, 16, 1241.
17. (a) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2002.
18. (b) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry, Wiley-VCH: Weinheim, 2005.
19. Kumar, R.; Selvam, C.; Kaur, G.; Chakraborti, A. K. Synlett 2005, 1401.
20. Chakraborti, A. K.; Selvam, C.; Kaur, G.; Bhagat, S. Synlett 2004, 851.
21. Bougrin, K.; Loupy, A.; Soufiaoui, M. Tetrahedron 1998, 54, 8055.
22. Rostamizadeh, S.; Derfshian, E. J. Chem. Res., Synop. 2001, 227.
23. Njoya, Y.; Gellis, A.; Crozet, M. P.; Vanelle, P. Sulfur Lett. 2003, 26, 67.
24. Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
25. Pottorf, R. S.; Chadha, N. K.; Katkevics, M.; Ozola, V.; Suna, E.; Ghane, H.; Regberg, T.; Player, M. R. Tetrahedron Lett. 2003, 44, 175.
26. Kamila, S.; Zhang, H.; Biehl, E. R. Heterocycles 2005, 65, 2119.
27. Paul, S.; Gupta, M.; Gupta, R. Synth. Commun. 2002, 32, 3541.
28. Villemin, D.; Hammadi, M.; Martin, B. Synth. Commun. 1996, 26, 2895.
29. Kodomari, M.; Tamaru, Y.; Aoyama, T. Synth. Commun. 2004, 34, 3029.
30. Rann, B. C.; Jana, R.; Dey, S. S. Chem. Lett. 2004, 33, 274.
31. Janssen, M. J. In The Chemistry of Carboxylic Acid and Esters; Patai, S., Ed.; Wiley: Chichester, 1969, 705-764.
32. Filippi, J.-J.; Fernandez, X.; Lizzani-Cuvelier, L.; Loiseau, A.-M. Tetrahedron Lett. 2003, 44, 6647.
33. Wu, X.; Mahalingam, A. K.; Alterman, M. Tetrahedron Lett. 2005, 46, 1501.
34. Valette, L.; Poulain, S.; Fernandez, X.; Lizzani-Cuvelier, L. J. Sulfur Chem. 2005, 26, 155.
35. Deng, S.-L.; Chen, R.-Y. Monatsh. Chem. 2004, 135, 1113.
36. Huang, H.-M; Yu, H.-T.; Chen, P.-L.; Han, J.; Meng, J.-B. Youji Huaxue 2004, 24, 502;
37. Chem. Abstr. 2004, 141, 295952.
38. Kiryanov, A. A.; Sampson, P.; Seed, A. J. J. Org. Chem. 2001, 66, 7925.
39. Jesberger, M.; Davis, T. P.; Barner, L. Synthesis 2003, 1929.
40. Pedersen, U.; Thorsen, M.; El-Khrisy, E. E. A. M.; Clausen, K.; Lawesson, S. O. Tetrahedron 1982, 38, 3267.
41. Shi, W.; Shafaei-Fallah, M.; Anson, C. E.; Rothenberger, A. J. Chem. Soc., Dalton Trans. 2005, 3909.
42. Lawesson reagent is used as purchased from Fluka (98% purity). Reactions must be carried out in an efficient fume hood.
43. +], 180 (7).
44. Yoshifuji, M.; Nagase, R.; Kawashima, T.; Inamoto, N. Heterocycles 1978, 10, 57.
45. Brewster, K.; Chittenden, R. A.; Harrison, J. M.; Inch, T. D.; Brown, C. J. Chem. Soc., Perkin Trans. 1 1976, 1291.
46. El-Sheikh, M. I.; Marks, A.; Biehl, E. R. J. Org. Chem. 1981, 46, 3256.
47. Yoshifuji, M.; Nagase, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1982, 55, 873.
48. Tauer, E.; Grellmann, K. H. J. Org. Chem. 1981, 46, 4252.
49. Bayh, O.; Awad, H.; Mongin, F.; Hoarau, C.; Bischoff, L.; Trecourt, F.; Queguiner, G.; Marsais, F.; Blanco, F.; Abarca, B.; Ballesteros, R. J. Org. Chem. 2005, 70, 5190.
50. Prakash, O.; Batra, A.; Sharma, V.; Saini, R. K.; Verma, R. S. J. Indian Chem. Soc. 2003, 80, 1031.
51. Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 6646.
52. Itoya, K.; Sawada, H.; Kakimoto, M.; Imai, Y. Macromolecules 1995, 28, 2611.
53. Bywater, W. G.; Coleman, W. R.; Kamm, O.; Merritt, H. J. Am. Chem. Soc. 1945, 67, 905.
54. 2S: C, 67.34; H, 5.30; N, 4.91. Found: C, 67.14; H, 5.28; N, 4.85.
55. Osuka, A.; Uno, Y.; Horiuchi, H.; Suzuki, H. Synthesis 1984, 145.
56. Mortimer, C. G.; Wells, G.; Crochard, J.-P.; Stone, E. L.; Bradshaw, T. D.; Stevens, M. F. G.; Westwell, A. D. J. Med. Chem. 2006, 49, 179.
57. Ulrich, H. In Science of Synthesis, Vol. 11; Schaumann, E., Ed.; Thieme: Stuttgart, 2001, 835-912.
58. Deligeorgiev, T. C. Dyes Pigm. 1990, 12, 243.
59. Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Heterocycles 2004, 63, 2769.
60. Tzanopoulou, S.; Pirmettis, I. C.; Patsis, G.; Raptopoulou, C.; Terzis, A.; Papadopoulos, M.; Pelecanou, M. Inorg. Chem. 2006, 45, 902.
61. Boger, D. L. J. Org. Chem. 1978, 43, 2296.
62. Elderfield, R. C.; McClenachan, E. C. J. Am. Chem. Soc. 1960, 82, 1982.
63. DuBrow, P. L.; Hoerr, C. W.; Harwood, H. J. J. Am. Chem. Soc. 1952, 74, 6241.
64. Shabana, R.; Atrees, S. S. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 105, 57.