Cyanuric chloride as promoter for the oxidation of sulfides and deoxygenation of sulfoxides

Tetrahedron Letters

Volumn 52, Issue 48, 2011, Pages 6420-6423

  Bahrami, Kiumars ^a   Khodaei, Mohammad M ^a   Sohrabnezhad, Samira ^a  

^a RAZI UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

CYANURIC CHLORIDE; SULFIDE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEOXYGENATION; ORGANIC CHEMISTRY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 80255140496     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.073     Document Type: Article

References (81)

1. (a) Patai, S.; Rappoport, Z. Synthesis of Sulfones, Sulfoxides, and Cyclic Sulfides; J. Wiley: Chichester, 1994;
2. (b) Organosulfur Chemistry I In Topics in Current Chemistry; Page, P. C. B., Ed.; Springer: Berlin, 1999; Vol. 204;
3. (c) Metzner, P.; Thuillier, A. Sulfur Reagents in Organic Synthesis; Academic Press: London, 1994.
4. (a) Madesclaire, M. Tetrahedron 1986, 42, 5459;
5. (b) Karmee, S. K.; Greiner, L.; Kraynov, A.; Muller, T. E.; Niemeijer, B.; Leitner, W. Chem. Commun. 2010, 46, 6705;
6. (c) Maciuca, A.-L.; Dumitriu, E.; Fajula, F.; Hulea, V. Chemosphere 2007, 68, 227;
7. (d) Al-Maksoud, W.; Daniele, S.; Sorokin, A. B. Green Chem. 2008, 10, 447;
8. (e) Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. A: Chem. 1997, 117, 397;
9. (f) Hulea, V.; Fajula, F.; Bousquet, J. J. Catal. 2001, 198, 179;
10. (g) Lu, H.; Gao, J.; Jiang, Z.; Yang, Y.; Song, B.; Li, C. Chem. Commun. 2007, 150;
11. (h) Kamata, K.; Hirano, T.; Mizuno, N. Chem. Commun. 2009, 3958;
12. (i) Choudary, B. M.; Reddy, C. R. V.; Prakash, B. V.; Kantam, M. L.; Sreedhar, B. Chem. Commun. 2003, 754.
13. (a) Cojocariu, A. M.; Mutin, P. H.; Dumitriu, E.; Fajula, F.; Vioux, A.; Hulea, V. Chem. Commun. 2008, 5357;
14. (b) Samanta, C. Appl. Catal. A 2008, 350, 133;
15. (c) Edwards, J. K.; Thomas, A.; Carley, A. F.; Herzing, A. A.; Kiely, C. J.; Hutchings, G. J. Green Chem. 2008, 10, 388;
16. (d) Jenzer, G.; Mallat, T.; Maciejewski, M.; Eigenmann, F.; Baiker, A. Appl. Catal. A 2001, 208, 125;
17. (e) Perez, D. I.; Grau, M. M.; Arends, I. W. C. E.; Hollmann, F. Chem. Commun. 2009, 6848;
18. (f) Mirkhani, V.; Tangestaninejad, S.; Moghadam, M.; Mohammadpoor- Baltork, I.; Saedi, Z. J. Iran. Chem. Soc. 2010, 7, 673.
19. (a) Kaczorowska, K.; Kolarska, Z.; Mitka, K.; Kowalski, P. Tetrahedron 2005, 61, 8315;
20. (b) Gregori, F.; Nobili, I.; Bigi, F.; Maggi, R.; Predieri, G.; Sartori, G. J. Mol. Catal. A: Chem. 2008, 286, 124;
21. (c) Jeyakumar, K.; Chand, D. K. Tetrahedron Lett. 2006, 47, 4573;
22. (d) Gamelas, C. A.; Lourenco, T.; da Costa, A. P.; Simplicio, A. L.; Royo, B.; Romao, C. C. Tetrahedron Lett. 2008, 49, 4708;
23. (e) Hussain, S.; Bharadwaj, S. K.; Pandey, R.; Chaudhuri, M. K. Eur. J. Org. Chem. 2009, 3319;
24. (f) Xian-Ying, S.; Jun-Fa, W. J. Mol. Catal. A: Chem. 2008, 280, 142;
25. (g) Bigi, F.; Corradini, A.; Quarantelli, C.; Sartori, G. J. Catal. 2007, 250, 222.
26. Bahrami, K.; Khodaei, M. M.; Sheikh Arabi, M. J. Org. Chem. 2010, 75, 6208.
27. (a) Bahrami, K.; Khodaei, M. M.; Kavianinia, I. Synthesis 2007, 547;
28. (b) Bahrami, K.; Khodaei, M. M.; Naali, F. J. Org. Chem. 2008, 73, 6835;
29. (c) Bahrami, K.; Khodaei, M. M.; Tirandaz, Y. Synthesis 2009, 369;
30. (d) Khodaei, M. M.; Bahrami, K.; Tirandaz, Y. J. Sulfur Chem. 2009, 30, 581;
31. (e) Bahrami, K.; Khodaei, M. M.; Farrokhi, A. Tetrahedron 2009, 65, 7658;
32. (f) Bahrami, K.; Khodaei, M. M.; Soheilizad, M. Synlett 2009, 2773;
33. (g) Bahrami, K.; Khodaei, M. M.; Soheilizad, M. J. Org. Chem. 2009, 74, 9287;
34. (h) Bahrami, K. Tetrahedron Lett. 2006, 47, 2009;
35. (i) Khodaei, M. M.; Bahrami, K.; Khedri, M. Can. J. Chem. 2007, 85, 7;
36. (j) Khodaei, M. M.; Bahrami, K.; Karimi, A. Synthesis 2008, 1682;
37. (k) Bahrami, K.; Khodaei, M. M.; Naali, F. Synlett 2009, 569;
38. (l) Khodaei, M. M.; Bahrami, K.; Sheikh Arabi, M. J. Sulfur Chem. 2010, 31, 83;
39. (m) Bahrami, K.; Khodaei, M. M.; Sheikh Arabi, M. Tetrahedron Lett. 2010, 51, 6939;
40. (n) Bahrami, K.; Khodaei, M. M.; Soheilizad, M. Tetrahedron Lett. 2010, 51, 4843;
41. (o) Bahrami, K.; Khodaei, M. M.; Tajik, M. Synthesis 2010, 4282;
42. (p) Bahrami, K.; Khodaei, M. M.; Fattahpour, P. Catal. Sci. Technol. 2011, 1, 389.
43. Bigdeli, M. A.; Heravi, M. M.; Mahdavinia, G. H. Catal. Commun. 2007, 8, 1595.
44. (a) Blotny, G. Tetrahedron 2006, 62, 9507;
45. (b) De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272.
46. Sharma, G. V. M.; Reddy, J. J.; Lakshmi, P. S.; Krishna, P. R. Tetrahedron Lett. 2004, 45, 7729.
47. Sharma, G. V. M.; Reddy, K. L.; Lakshmi, P. S.; Krishna, P. R. Synthesis 2006, 55.
48. Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2003, 44, 3855.
49. Bandgar, B. P.; Joshi, N. S.; Kamble, V. T. Tetrahedron Lett. 2006, 47, 4775.
50. Smolin, E. M.; Rapoport, L. S-Triazines and Derivatives In The Chemistry of Heterocyclic Compounds; Weissberger, A., Ed.; Interscience: New York, NY, 1959; Vol. 13, pp 17-48.
51. Hoggarth, E. J. Chem. Soc. 1949, 3311.
52. (a) Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469;
53. (b) Harpp, D. N.; Gleason, J.; Ash, D. K. J. Org. Chem. 1971, 36, 322.
54. Venier, C. G.; Squires, T. G.; Chen, Y.-Y.; Hussmann, G. P. J. C.; Shei, B. F.; Smith J. Org. Chem. 1982, 47, 3773.
55. Kaldor, S. W.; Hammond, M. Tetrahedron Lett. 1991, 32, 5043.
56. Black, S.; Harte, E. M.; Hudson, B.; Wartofsky, L. J. Biol. Chem. 1960, 235, 2910.
57. (a) Khurana, J. M.; Ray, A.; Singh, S. Tetrahedron Lett. 1998, 39, 3829;
58. (b) Karimi, B.; Zareyee, D. Synthesis 2003, 1875;
59. (c) Iranpoor, N.; Firouzabadi, H.; Shaterian, H. R. J. Org. Chem. 2002, 67, 2826;
60. (d) Karimi, B.; Zareyee, D. Synthesis 2003, 335;
61. (e) Posner, G. H.; Tang, P. W. J. Org. Chem. 1978, 43, 4131;
62. (f) Madesclaire, M. Tetrahedron 1988, 44, 6537.
63. (a) Firouzabadi, H.; Karimi, B. Synthesis 1999, 500;
64. (b) Yoo, B.; Choi, K. H.; Kim, D. Y.; Choi, K. I.; Kim, J. H. Synth. Commun. 2003, 33, 53;
65. (c) Miller, S. J.; Collier, T. R.; Wu, W. Tetrahedron Lett. 2000, 41, 3781;
66. (d) Olah, G. A.; Fung, A. P.; Gupta, B. G. B.; Narang, S. C. Synthesis 1980, 221.
67. (a) Szmant, H. H.; Cox, O. J. Org. Chem. 1966, 31, 1595;
68. (b) Kikuchi, S.; Konishi, H.; Hashimoto, Y. Tetrahedron 2005, 61, 3587;
69. (c) Kikuchi, S.; Hashimoto, Y. Synlett 2004, 1267;
70. (d) Hashimoto, Y.; Konishi, H.; Kikuchi, S. Synlett 2004, 1264;
71. (e) Hashimoto, Y.; Kikuchi, S. Chem. Lett. 2002, 126.
72. (a) Harrison, D. J.; Tam, N. C.; Vogels, C. M.; Langler, R. F.; Baker, R. T.; Decken, A.; Westcott, S. A. Tetrahedron Lett. 2004, 45, 8493;
73. (b) Palazzi, C.; Colombo, L.; Gennari, C. Tetrahedron Lett. 1986, 27, 1735;
74. (c) Suzuki, I.; Yamamoto, Y. J. Org. Chem. 1993, 58, 4783;
75. (d) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390;
76. (e) Bahrami, K.; Khodaei, M. M.; Karimi, A. Synthesis 2008, 2543;
77. (f) Bahrami, K.; Khodaei, M. M.; Khedri, M. Chem. Lett. 2007, 36, 1324.
78. Deligeorgiev, T.; Kaloyanova, S.; Lesev, N.; Vaquero, J. J. Ultrason. Sonochem. 2010, 17, 783.
79. Fong, H. O.; Hardstaff, W. R.; Kay, D. G.; Langler, R. F.; Morse, R. H.; Sandoval, D.-N. Can. J. Chem. 1979, 57, 1206.
80. Shimizu, M.; Shibuya, K.; Hayakawa, R. Synlett 2000, 1437.
81. Esteban, A. L.; Diez, E. Can. J. Chem. 1980, 58, 2340.