Synthesis of α-iodo β-ketosulfones and α-iodo methylsulfones using iodine monochloride

Tetrahedron Letters

Volumn 47, Issue 26, 2006, Pages 4319-4323

  Suryakiran, N ^a   Srikanth Reddy, T ^a   Suresh, V ^a   Lakshman, M ^a   Venkateswarlu, Y ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Iodo ketosulfones; Iodo methylsulfones; Ketosulfones

Indexed keywords

ACETIC ACID; ALKALI; ALPHA IODO BETA KETOSULFONE DERIVATIVE; ALPHA IODO METHYLSULFONE DERIVATIVE; CHLORIDE; IODINE; IODINE MONOCHLORIDE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; ROOM TEMPERATURE;

EID: 33646763200     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.123     Document Type: Article

References (57)

1. Simpkins N.S. In: Baldwin J.E. (Ed). Sulfones in Organic Synthesis (1993), Pergamon Press, Oxford
2. Macro J.L., Fernandez I., Khira N., Fernandez P., and Romero A. J. Org. Chem. 60 (1995) 6678
3. Reddy M.V.R., and Reddy S. Acta Chim. Hung. 115 (1984) 269
4. Ihara M., Suzuki S., Taniguchi T., Tokunaga Y., and Fukumoto K. Tetrahedron 51 (1995) 9873
5. Baldwin J.E., Adlington R.M., Crouch N.P., Hill R.L., and Laffeg T.G. Tetrahedron Lett. 36 (1995) 7925
6. Reddy M.V.R., and Reddy S. Acta Chim. Hung. 120 (1985) 275
7. Looker J.J. J. Org. Chem. 31 (1966) 2714
8. Sengupta S., Sarma D.S., and Mondal S. Tetrahedron 54 (1998) 9791
9. Sengupta S., Sarma D.S., and Mondal S. Tetrahedron: Asymmetry 12 (2001) 513
10. Sengupta S., Sarma D.S., and Mondal S. Tetrahedron: Asymmetry 9 (1998) 2311
11. Marco J.L., Fernandez I., Khiar N., Fernandez P., and Romero A. J. Org. Chem. 60 (1995) 6678
12. Marco J.L. J. Org. Chem. 62 (1997) 6575
13. Corey E.J., and Chavosky M. J. Am. Chem. Soc. 86 (1964) 1639
14. Trost B.M., Arndt H.C., Strege P.E., and Verhowever T.R. Tetrahedron Lett. 27 (1976) 3477
15. Kurth M.J., and Brien M.J. J. Org. Chem. 50 (1985) 3846
16. Fuju M., Nakamura K., Mekata H., Oka S., and Ohno A. Bull. Chem. Soc. Jpn. 61 (1988) 495
17. Sengupta S., Sarma D.S., and Mondal S. Tetrahedron 54 (1998) 9791
18. Guo H., and Zhang Y. Synth. Commun. 30 (2005) 2564
19. Svatos A., Hun Kova Z., Kren V., Hoskovec M., Saman D., Valterova I., Vrkoc J., and Koutek B. Tetrahedron: Asymmetry 7 (1996) 1285
20. Betus P., Phansavath P., Vidal V.R., Genet J.P., Touati A.R., Homri T., and Hassine B.B. Tetrahedron: Asymmetry 10 (1999) 1369
21. Gotor V., Rebolledo F., and Liz R. Tetrahedron: Asymmetry 12 (2001) 513
22. Grossert J.S., Dubey P.K., Gill G.H., Cameron T.S., and Gardner P.A. Can. J. Chem. 62 (1984) 174 and references cited therein
23. Jonczyk A., Banko K., and Makosza M. J. Org. Chem. 40 (1975) 266
24. Lee J.W., and Oh D.Y.S. Synth. Commun. 20 (1990) 273
25. Bardwell F.G., and Coopert G.D. J. Am. Chem. Soc. 73 (1951) 5184
26. Reutrakal V., Prapansiri V., and Panyachotipun C. Tetrahedron Lett. 25 (1984) 1949
27. Adamczy K.M., Dolence E.K., Watt D.S., Christy M.R., Reibenspies J.H., and Anderson O.P. J. Org. Chem. 49 (1984) 1378
28. Dolence E.K., Adamczy K.M., Watt D.S., Rasell G.B., and Horn D.H.S. Tetrahedron Lett. 26 (1985) 1189
29. Arai S., Ishidu T., and Shioiri T. Tetrahedron Lett. 39 (1998) 8299
30. Nagashima E., Suzuki K., Ishikawa M., and Sekiya M. Heterocycles 23 (1985) 1873
31. Trost B.M. Comprehensive Organic Chemistry Vol. 1 (1993), Pergamon Press p 530
32. Golinski J., and Makosza M. Tetrahedron Lett. 37 (1978) 3495
33. Makosza M., Chylinska B., and Mudryk B. Ann. Chem. 1 (1984) 8
34. Wojciechowski K., and Makosza M. Tetrahedron Lett. 62 (1989) 4793
35. Wojciechowki K., and Makosza M. Synthesis 8 (1986) 651
36. Takhashi M., and Suga D. Synthesis 7 (1998) 986
37. Oishi, Y.; Watanabe, T.; Kusa, K.; Kazama, M.; Koniya, K. Japanese Patent, October 7, 1988, JP 63243067; CAN 110, 212359.
38. Shigematsy, S.; Yamada, Y.; Kimura, I. Japanese Patent, July 30, 1983; JP 58128305, 99, 171339.
39. Baker, F. C.; Li, J. P. N. United States Patent, January 27, 1981; US 4247559, (C07D 207/452; A61K 031/40).
40. Eckstein Z., Zavistowska M., Palut D., and Polubiec E. Pol. J. Chem. 45 (1966) 314
41. Ejmocki Z., Krassowska B.K., Olezak I., and Eckstein Z. Pol. J. Chem. 54 (1980) 11 and 2153
42. Antane S., Bernotas R., Li Y., David Mc.R., and Yan Y. Synth. Commun. 34 (2004) 2443
43. Middlebos W., Strating J., and Zwanenberg B. Tetrahedron Lett. 12 (1971) 351
44. Ziegler W.M., and Conner R. J. Am. Chem. Soc. 62 (1940) 2596
45. Barr E., Ziegler W.M., and Conner R. J. Am. Chem. Soc. 63 (1941) 106
46. Kresze G., Schram W.M., and Cleve G. Chem. Ber. 94 (1961) 2060
47. Baughman T.W., Sworen J.C., and Wagener K.B. Tetrahedron 60 (2004) 10943
48. Kim D.W., Song C.E., and Chi D.Y. J. Org. Chem. 68 (2003) 4281
49. Bordwell F.G., and Brannen Jr. W.T. J. Am. Chem. Soc. 86 (1964) 4645 and references cited therein
50. Bordwell F.G., and Bruce B.J. J. Org. Chem. (1967) 1182 and references cited therein
51. Canant J.B., and Kirner W.R. J. Am. Chem. Soc. 46 (1924) 232
52. Bordwell F.G., and Coope G.D. J. Am. Chem. Soc. 73 (1951) 5184
53. Bordwell F.G., and Brannen Jr. W.T. J. Am. Chem. Soc. 86 (1964) 4645
54. Stewart S.K., and Whiting A. Tetrahedron Lett. 36 (1995) 3929
55. Suryakiran N., Srikanth Reddy T., Asha Latha K., Lakshman M., and Venkateswarlu Y. Tetrahedron Lett. 47 (2006) 3853-3856
56. Ramaiah K., Dubey P.K., and Ramanandham J. Indian J. Chem. 38 (1999) 297
57. Holst E.H., and Fernelius W.C. J. Org. Chem. (1958) 1881