1,3-dibromo-5,5-dimethylhydantoin (DBH) as a mild and efficient catalyst for chemoselective thioacetalization of carbonyl compounds and dethioacetalization under mild conditions

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 185, Issue 4, 2010, Pages 689-696

  Veisi, Hojat ^a   Amiri, Mostafa ^b   Hamidian, Amir Hossein ^c   Malakootikhah, Javad ^d   Fatolahi, Leila ^a   Faraji, Alireza ^b   Sedrpoushan, Alireza ^e   Maleki, Behrooz ^f   Saremi, Shokufe Ghahri ^a   Noroozi, Mohammad ^g   Bahadoori, Fatemeh ^h   Veisi, Somayeh ^a  

^a PAYAME NOOR UNIVERSITY   (Iran)

^b BU ALI SINA UNIVERSITY   (Iran)

^c UNIVERSITY OF OTAGO   (New Zealand)

^d UNIVERSITY OF TEHRAN   (Iran)

^e IRANIAN RESEARCH ORGANIZATION FOR SCIENCE AND TECHNOLOGY IROST   (Iran)

^f HAKIM SABZEVARI UNIVERSITY   (Iran)

^g Research Institute of Petroleum Industry (PIPI)   (Iran)

^h ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Carbonyl compounds; DBH; Deprotection; Thioacetalization

Indexed keywords

EID: 77951209657     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500902917669     Document Type: Article

References (46)

1. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed. (JohnWiley and Sons Inc., New York, 1999), pp. 329-344.
2. T. W. Greene, Protective Groups in Organic Synthesis (John Wiley: NewYork, 1981), p. 129.
3. H. Yu, D. Dong, Y. Ouyang, and Q. Liu, Can. J. Chem., 83, 1741 (2005).
4. L. Battaglia, F. Pinna, and G. Strukul, Can. J. Chem., 79, 621 (2001).
5. P. C. Bulman Page, J. C. Prodger, and D. Westwood, Tetrahedron, 49, 10355 (1993).
6. T. Nakata, S. Nagao, S. Mori, and T. Oishi, Tetrahedron Lett., 26, 6461 (1985).
7. D. V. Evans, L. K. Truesdale, K. G. Grimm, and S. L. Nesbitt, J. Am. Chem. Soc., 99, 5009 (1977).
8. B. C. Ong, Tetrahedron Lett., 21, 4225 (1980).
9. S. Muthusamy, S. Arulananda Babu, and C. Gunanathan, Tetrahedron Lett., 42, 359 (2001).
10. B. F. Mirjalili, M. A. Zolfigol, A. Bamoniri, M. A. Amrolahi, and A. Hazar, Phosphorus, Sulfur, and Silicon, 179, 1397 (2004).
11. N. Gupta, S. L. Goverdhan, and J. Singh, Catal. Commun., 8, 1323 (2007).
12. H. Firouzabadi, N. Iranpoor, and B. Karimi, Synthesis, 58 (1999).
13. T. H. Khan, E. Mondal, D. R. Sahu, and S. Islam, Tetrahedron Lett., 44, 919 (2003).
14. H. Firouzabadi, N. Iranpoor, and H. Hazarkhani, Synlett, 1641 (2001).
15. A. Kamal and G. Chouhan, Synlett, 474 (2002).
16. H. Firouzabadi, N. Iranpoor, and H. Hazarkhani, J. Org. Chem., 66, 7527 (2001).
17. G. Bez and D. Gogoi, Tetrahedron Lett., 47, 5155 (2006).
18. V. T. Kamble, B. P. Bandgar, D. B. Muley, and N. S. Joshi. J. Mol. Catal. A: Chem., 268, 70 (2007).
19. S. K. De, Tetrahedron Lett., 45, 2339 (2004).
20. S. K. De, J. Mol. Catal. A: Chem., 226, 77 (2005).
21. S. K. De, Synthesis, 828 (2004).
22. B. Karimi and M. Khalkhali, J. Mol. Catal. A: Chem., 271, 76 (2007).
23. J. S. Yadav, B. V. S. Reddy, S. Raghavendra, and M. Satyanarayana, Tetrahedron Lett., 43, 4679 (2002).
24. N. Komatsu, M. Uda, and H. Suzuki, Synlett, 984 (1995).
25. F. M. Moghadam, H. Z. Boeini, D. Zargarani, and G. R. Bardajee, Synth. Commun., 36, 1093 (2006).
26. A. R. Hajipour, S. E. Mallakpour, I. M. Baltork, and H. Adibi, Molecules, 7, 674 (2002).
27. J. B. Chattopadhyaya and A. V. Ramarao, Tetrahedron Lett., 58, 3735 (1973).
28. G. A. Olah, A. K. Mehrotra, and S. C. Narang, Synthesis, 151 (1982).
29. E. J. Corey and B. W. Erickson, J. Org. Chem., 36, 3553 (1971).
30. H. Firouzabadi, N. Iranpoor, and M. A. Zolfigol, Bull. Chem. Soc. Jpn., 71, 2169 (1998).
31. L. Mathew and S. Sankararaman, J. Org. Chem., 58, 7576 (1993).
32. H. Tani, T. Inamasu, K. Masumoto, R. Tamura, H. Shimizu, and H. Suzuki, Phosphorus, Sulfur, and Silicon, 67, 261 (1992).
33. C. S. Rao, M. Chandrasekharam, H. Ila, and H. Junjappa, Tetrahedron Lett., 33, 8163, (1992).
34. A. S. Kiselyov and L. Strekowski, Tetrahedron, 49, 2151 (1993).
35. M. Kamata, M. Sato, and E. Hasegawa, Tetrahedron Lett., 33, 5085 (1992).
36. H. Firouzabadi, N. Iranpoor, and H. Hazarkhani, Phosphorus, Sulfur, and Silicon, 177, 2571 (2002).
37. H. Firouzabadi, N. Iranpoor, H. Hazarkhani, and B. Karimi, J. Org. Chem., 67, 2572 (2002).
38. R. Ghorbani-Vaghei and M. A. Zolfigol, J. Chin. Chem. Soc., 52, 327 (2005).
39. M. Curini, M. C. Marcotullio, E. Pisani, and O. Rosati, Synlett, 769 (1997).
40. J. Cossy, Synthesis, 1113 (1987).
41. S. A. Haroutounian, Synthesis, 39 (1995).
42. E. J. Corey and M. G. Bock, Tetrahedron Lett., 16, 2643 (1975).
43. M. H. Habibi, S. Tangestaninejad,M.Montazerzohori, and I.Mohamadpoor-Baltork, Molecules, 8, 663 (2003).
44. U. V. Desai, D. M. Pore, B. V. Tamhankar, S. A. Jadhav, and P. P. Wadgaonkar, Tetrahedron Lett., 47, 8559 (2006).
45. A. Kamal and G. Chouhan, Tetrahedron Lett., 43, 1347 (2002).
46. S. K. De, Tetrahedron Lett., 45, 1035 (2004).