Zinc perchlorate hexahydrate as a new and highly efficient catalyst for synthesis of 2-hydroxysulfides by opening of epoxide rings with thiols under solvent-free conditions: Application for synthesis of the key intermediate of diltiazem

Journal of Molecular Catalysis A: Chemical

Volumn 263, Issue 1-2, 2007, Pages 137-142

  Shivani, ^a   Chakraborti, Asit K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

2 Hydroxysulfides; Catalyst; Chemoselective; Epoxides; Intermediate of diltiazem; Regioselective; Solvent free; Thiols; Zinc perchlorate hexahydrate

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; CHLORINE; OLEFINS; SOLVENTS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

2-HYDROXYSULFIDES; ACYCLIC OLEFINES; EPOXIDE RINGS; REGIOSELECTIVE;

ZINC COMPOUNDS;

EID: 33846568507     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.08.047     Document Type: Article

References (56)

1. Corey E.J., Clark D.A., Goto G., Marfat A., Mioskowski C., Sameulson B., and Hammerson S. J. Am. Chem. Soc. 102 (1980) 1436
2. Luly J.R., Yi N., Soderquist J., Stein H., Cohen J., Perun T.J., and Plattner J.J. J. Med. Chem. 30 (1987) 1609
3. Hashiyama T. Med. Res. Rev. 20 (2000) 485
4. Onaka M., Sugita K., Takeuchi H., and Izumi. J. Chem. Soc. Chem. Commun. (1988) 1173
5. Iizawa T.Y., Goto A., and Nishikubo T. Bull. Chem. Soc. Jpn. 62 (1989) 597
6. Takeuchi H., Kitajima K., Yamamoto Y., and Mizuno K. J. Chem. Soc. Perkin Trans. 2 (1993) 199
7. Brittain J., and Gareau Y. Tetrahedron Lett. 34 (1993) 3363
8. Albanese D., Landini D., and Penso M. Synthesis (1994) 34
9. Tanabe Y., Mori K., and Yoshida Y. J. Chem. Soc. Perkin Trans. 1 (1997) 671
10. de Pomar J.C.J., and Soderquist J.A. Tetrahedron Lett. 39 (1998) 4409
11. Polshettiwar V., and Kaushik M.P. Catal. Commun. 5 (2004) 515
12. Fringuelli F., Pizzo F., and Vaccaro L. J. Org. Chem. 69 (2004) 2315
13. Posner G.H., Rogers D.Z., Charles M.K., and Gurria G.M. Tetrahedron Lett. (1975) 3597
14. Posner G.H., and Rogers D.Z. J. Am. Chem. Soc. 99 (1977) 8208
15. Hashiyama T., Inoue H., Konda M., and Takeda M. J. Chem. Soc. Perkin Trans. 1 (1984) 1725
16. Caron M., and Sharpless K.B. J. Org. Chem. 50 (1985) 1557
17. Chong J.M., and Sharpless K.B. J. Org. Chem. 50 (1985) 1563
18. Vougioukas A.E., and Kagan H.B. Tetrahedron Lett. 28 (1987) 6065
19. Yamashita S. Bull. Chem. Soc. Jpn. 61 (1988) 1213
20. Guivisdalsky P.N., and Bittman R. J. Am. Chem. Soc. 111 (1989) 3077
21. Iqbal J., Panday A., Shukla A., Srivastava R.R., and Tripathi S. Tetrahedron 46 (1990) 6423
22. Iranpoor N., Baltork M., and Zardaloo S. Tetrahedron 47 (1991) 9861
23. Maiti A.K., Biswas G.K., and Bhattacharyya P. J. Chem. Res. (S) (1997) 325
24. Mojtahedi M.M., Ghasemi M.H., Abaee M.S., and Bolourtchian M. ARKIVOC xv (2005) 68
25. Iida T., Yamamoto N., Sasai H., and Shibasaki M. J. Am. Chem. Soc. 119 (1997) 4783
26. Wu M.H., and Jacobson E.N. J. Org. Chem. 63 (1998) 5252
27. Wu J., Hou X.L., Dai L.X., Xia L.J., and Tang M.H. Tetrahedron Asymm. 9 (1998) 3431
28. Yadav J.S., Reddy B.V.S., and Baishya G. Chem. Lett. (2002) 906
29. Fringuelli F., Pizzo F., Tortoioli S., and Vaccaro L. Tetrahedron Lett. 44 (2003) 6785
30. Chandrasekhar S., Reddy C.R., Babu B.N., and Chandrasekhar G. Tetrahedron Lett. 43 (2002) 3801
31. Cossy J., Bellosta V., Hamoir C., and Desmurs J.-R. Tetrahedron Lett. 43 (2002) 7083
32. Amantini D., Fringuelli F., Pizzo F., Tortoioli S., and Vaccaro L. Synlett (2003) 2292
33. Maiti A.K., and Bhattacharyya P. Tetrahedron 50 (1994) 10483
34. Kesavan V., Bonnet-Delpon D., and Bégué J.-P. Tetrahedron Lett. 41 (2000) 2895
35. Fan R.-H., and Hou X.-L. J. Org. Chem. 68 (2003) 726
36. Olah G.A., and Prakash G.K.S. Superacids (1985), Wiley, New York
37. Dumeunier R., and Markó I.E. Tetrahedron Lett. 45 (2004) 825
38. Long J.R. Chem. Health Safety (2002) 12
39. Chakraborti A.K., Gulhane R., and Shivani. Synthesis (2003) 1805
40. Chakraborti A.K., Sharma L., Gulhane R., and Shivani. Tetrahedron 59 (2003) 7661
41. Chakraborti A.K., Bhagat S., and Rudrawar S. Tetrahedron Lett. 45 (2004) 7641
42. Garg S.K., Kumar R., and Chakraborti A.K. Synlett (2005) 1370
43. Kumar R., Thilagavathi R., Gulhane R., and Chakraborti A.K. J. Mol. Catal. A: Chem. 250 (2006) 227
44. Chini M., Crotti P., Giovani E., Macchia F., and Pineschi M. Synlett (1992) 303
45. Azizi N., and Saidi M.R. Catal. Commun. 7 (2006) 224
46. Huhey J.E. Inorganic Chemistry: Principles of Structure and Reactivity. 3rd ed. (1990), Harper & Row, Singapore
47. Casachi A., Desimoni G., Faita G., Invernizzi A.G., Lanati S., and Righetti P. J. Am. Chem. Soc. 115 (1993) 8002
48. Yatsimirskii K.B., and Vasil'ev V.P. Instability Constants of Complex Compounds (1960), Pergamon Press, Elmsford, NY
49. Chakraborti A.K., Kondaskar A., and Rudrawar S. Tetrahedron 60 (2004) 9085
50. Chakraborti A.K., Rudrawar S., and Kondaskar A. Org. Biomol. Chem. 2 (2004) 1277
51. Chakraborti A.K., Rudrawar S., and Kondaskar A. Eur. J. Org. Chem. (2004) 3597
52. Chakraborti A.K., and Kondaskar A. Tetrahedron Lett. 44 (2003) 8315
53. McClure D.E., Arison B.H., and Baldwin J.J. J. Am. Chem. Soc. 101 (1979) 3666
54. Rongshi L., Farmer P.S., Xie M., Quilliam M.A., Pleasance S., Howlett S.E., and Yeung P.K.F. J. Med. Chem. 35 (1992) 3246
55. de Groot A., and Jansen B.J.M. Synthesis (1985) 434
56. Garrett R.L. Designing safer chemicals. In: Garrett R.L., and De Vito S.C. (Eds). American Chemical Society Symposium Series 640. Washington, DC (1996)