Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H 2O 2-POCl 3 system

Tetrahedron

Volumn 68, Issue 25, 2012, Pages 5095-5101

  Bahrami, Kiumars ^a   Khodaei, Mohammad M ^a   Abbasi, Jamshid ^a  

^a RAZI UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

3 (N 4 TOLYLSULFAMOYL) PROPANE 1 SULFONYL CHLORIDE; 4 TOLYL CYCLOHEXANESULFONATE; ACETONITRILE; AMINE; DIP TOLYL PROPANE 1,3 DISULFONATE; ESTER DERIVATIVE; HYDROGEN PEROXIDE; N1,N3 DICYCLOHEXYLPROPANE 1,3 DISULFONAMIDE; NAPHTHALEN 2 YL PHENYLMETHANESULFONATE; PHENOL DERIVATIVE; PHENYL NAPHTHALENE 2 SULFONATE; PHOSPHORUS OXYCHLORIDE; POLACRILIN; REAGENT; SULFONAMIDE; SULFONIC ESTER DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; NUCLEOPHILICITY; PRIORITY JOURNAL; ROOM TEMPERATURE; STEREOSPECIFICITY; SYNTHESIS;

EID: 84861528547     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.04.040     Document Type: Article

References (80)

1. C.T. Supuran, A. Casini, and A. Scozzafava Med. Res. Rev. 5 2003 535 558
2. A. Scozzafava, T. Owa, A. Mastrolorenzo, and C.T. Supuran Curr. Med. Chem. 10 2003 925 953
3. W.G. Harter, H. Albrect, K. Brady, B. Caprathe, J. Dunbar, J. Gilmore, S. Hays, C.R. Kostlan, B. Lunney, and N. Walker Bioorg. Med. Chem. Lett. 14 2004 809 812
4. N.S. Reddy, M.R. Mallireddigari, K.G. Cosenza, S.C. Bell, E.P. Reddy, and M.V.R. Reddy Bioorg. Med. Chem. Lett. 14 2004 4093 4097
5. B.R. Stranix, J.-F. Lavallee, G. Sevigny, J. Yelle, V. Perron, N. Leberre, D. Herbart, and J.J. Wu Bioorg. Med. Chem. Lett. 16 2006 3459 3462
6. T. Owa, H. Yoshino, T. Okauchi, K. Yoshimatsu, Y. Ozawa, N.H. Sugi, T. Nagasu, N. Koyanagi, and K. Kitoh J. Med. Chem. 42 1999 3789 3799
7. R.C. Ogden, and C.W. Flexner Protease Inhibitors in AIDS Therapy 2001 Marcel Dekker New York, NY, Basel
8. H. Nishida, T. Hamada, and O. Yonemitsu J. Org. Chem. 53 1988 3386 3387
9. W. Yuan, K. Fearson, and M.H. Gelb J. Org. Chem. 54 1989 906 910
10. J.F. O'Connell, and H. Rapoport J. Org. Chem. 57 1992 4775 4777
11. S. Chandrasekhar, and S. Mohapatra Tetrahedron Lett. 39 1998 695 698
12. C.G. Frost, J.P. Hartley, and D. Griffin Synlett 2002 1928 1930
13. T. Pandya, T. Murashima, L. Tedeschi, and A.G.M. Barrett J. Org. Chem. 68 2003 8274 8276
14. J.W. Lee, Y.Q. Louie, D.P. Walsh, and Y.-T. Chang J. Comb. Chem. 5 2003 330 335
15. S. Caddick, J.D. Wilden, and D.B. Judd J. Am. Chem. Soc. 126 2004 1024 1025
16. A.R. Katritzky, A.A.A. Adbel-Fattah, A.V. Vakulenko, and H. Tao J. Org. Chem. 70 2005 9191 9197
17. S.W. Wright, and K.N. Hallstrom J. Org. Chem. 71 2006 1080 1084
18. K.K. Anderson D.N. Jones, Comprehensive Organic Chemistry Vol. 3 1979 Pergamon Oxford
19. A. Yasuhara, M. Kameda, and T. Sakamoto Chem. Pharm. Bull. 47 1999 809 812
20. I. Singh, A.K. Rehni, R. Kalra, G. Joshi, M. Kumar, and H.Y. Aboul-Enei FABAD J. Pharm. Sci. 32 2007 91 100
21. P. Barbaro, and F. Liguori Chem. Rev. 109 2009 515 529
22. S.D. Alexandratos Ind. Eng. Chem. Res. 48 2009 388 398
23. J. Kammerer, R. Carle, and D.R. Kammerer J. Agric. Food Chem. 59 2011 22 42
24. M. Streat Ind. Eng. Chem. Res. 34 1995 2841 2848
25. R. Kunian Ion Exchange Resins 2nd ed. 1958 John Wiley and Sons New York, NY
26. R.W. Hein, M.J. Astle, and J.R. Shelton J. Org. Chem. 26 1961 4874 4878
27. E.D. Bergmann, and R. Corett J. Org. Chem. 23 1958 1507 1510
28. W.R. Boehme, and J. Xoo J. Org. Chem. 26 1961 3589 3591
29. M. Gordon, M.L. Depamphilis, and C.E. Griflin J. Org. Chem. 28 1963 698 700
30. P. Price, and S.S. Israelstam J. Org. Chem. 29 1964 2800 2802
31. M.J. Astle, and J.A. Oscar J. Org. Chem. 26 1961 1713 1715
32. N.N. Greenwood, and A. Earnshaw Chemistry of the Elements 2nd ed. 1997 Butterworth-Heinemann Oxford, UK
33. A.D.F. Toy The Chemistry of Phosphorus 1973 Pergamon Oxford, UK
34. R.C. Elderfield Heterocyclic Compounds vol. 6 1957 Wiley New York, NY pp 265-266
35. B.J. Walker Organophosphorus Chemistry pp 101-116 1972 Penguin Harmondsworth, UK
36. K. Hosoi, K. Nozaki, and T. Hiyama Org. Lett. 4 2002 2849 2851
37. S. Mons, N. Sabourault, E. Klein, C. Mioskowski, and L. Lebeau Tetrahedron Lett. 42 2001 7547 7549
38. M.S. Balakrishna, and B. Kaboudin Tetrahedron Lett. 42 2001 1127 1129
39. K. Bahrami, M.M. Khodaei, and M. Soheilizad J. Org. Chem. 74 2009 9287 9291
40. K. Bahrami, M.M. Khodaei, and M. Soheilizad Tetrahedron Lett. 51 2010 4843 4846
41. K. Bahrami, M.M. Khodaei, and I. Kavianinia Synthesis 2007 547 550
42. K. Bahrami, M.M. Khodaei, and F. Naali J. Org. Chem. 73 2008 6835 6837
43. K. Bahrami, M.M. Khodaei, and Y. Tirandaz Synthesis 2009 369 371
44. K. Bahrami, M.M. Khodaei, and A. Farrokhi Tetrahedron 65 2009 7658 7661
45. K. Bahrami, M.M. Khodaei, and M. Soheilizad Synlett 2009 2773 2776
46. K. Bahrami Tetrahedron Lett. 47 2006 2009 2012
47. K. Bahrami, M.M. Khodaei, and F. Naali Synlett 2009 569 572
48. K. Bahrami, M.M. Khodaei, and M. Sheikh Arabi Tetrahedron Lett. 51 2010 6939 6941
49. K. Bahrami, M.M. Khodaei, and M. Tajik Synthesis 2010 4282 4286
50. K. Bahrami, M.M. Khodaei, and P. Fattahpour Catal. Sci. Technol. 1 2011 389 393
51. K. Bahrami, M.M. Khodaei, and M. Sheikh Arabi J. Org. Chem. 75 2010 6208 6213
52. T.P. Johnston, C.L. Kussner, and L.B. Holum J. Org. Chem. 25 1960 399 402
53. J. Hoyle S. Patai, Z. Rappoport, The Chemistry of Sulphonic Acids, Esters, and their Derivatives 1991 John Wiley and Sons New York, NY
54. V.E. Marquez, R. Sharma, S. Wang, N.E. Lewin, P.M. Blumberg, I. Kim, and J. Lee Bioorg. Med. Chem. Lett. 8 1998 1757 1762
55. T. Heiner, S.I. Kozhushkov, M. Noltemeyer, T. Haumann, R. Boese, and A. de Meijere Tetrahedron 52 1996 12185 12196
56. J.F. King, S. Skonieczny, and G.A. Poole Can. J. Chem. 61 1983 235 243
57. Y.S. Choe, J.A. Katzenellenbogen, and T. Lett Tetrahedron Lett. 34 1993 1579 1580
58. J.H. Choi, B.C. Lee, H.W. Lee, and I. Lee J. Org. Chem. 67 2002 1277 1282
59. H. Schirmeister, and W. Pfleiderer Helv. Chim. Acta 77 1994 10 22
60. G. Quinkert, E. Fernholz, P. Eckes, D. Neumann, and G. Duerner Helv. Chim. Acta 72 1989 1753 1786
61. C. Dufresne, M. Gallant, Y. Gareau, R. Ruel, L. Trimble, and M. Labelle J. Org. Chem. 61 1996 8518 8525
62. A. Windaus, and E. Kuhr Liebigs Ann. Chem. 532 1937 52 68
63. W. Treibs, and I. Lorenz Chem. Ber. 82 1949 400 405
64. G. Geiseler, and R. Kuschmiers Chem. Ber. 91 1958 1881 1891
65. H.C. Hansen, and J.L. Kice J. Org. Chem. 48 1983 2943 2948
66. C.O. Meese Synthesis 1984 1041 1042
67. T. Reichstein, and W. Schindler Helv. Chim. Acta 23 1940 669 675
68. R.B. Scott, and R.E. Lutz J. Org. Chem. 19 1954 830 839
69. P. Purushottamachar, A. Khandelwal, T.S. Vasaitis, R.D. Bruno, L.K. Gediya, and V.C.O. Njar Bioorg. Med. Chem. 16 2008 3519 3529
70. J. Meinwald, S. Knapp, S.K. Obendorf, and R.E. Hughes J. Am. Chem. Soc. 98 1976 6643 6649
71. D. Hellwinkel, and M. Supp Chem. Ber. 109 1976 3749 3766
72. H.R. Snyder, and R.E. Heckert J. Am. Chem. Soc. 74 1952 2006 2009
73. M. Katohgi, and H. Togo Tetrahedron 57 2001 7481 7486
74. A.R. Katritzky, V. Rodriguez-Garcia, and S.K. Nair J. Org. Chem. 69 2004 1849 1852
75. F. Rolla J. Org. Chem. 47 1982 4327 4329
76. L. De Luca, and G. Giacomelli J. Org. Chem. 73 2008 3967 3969
77. D.A. Wilson, C.J. Wilson, C. Moldoveanu, A.-M. Resmerita, P. Corcoran, L.M. Hoang, B.M. Rosen, and V. Percec J. Am. Chem. Soc. 132 2010 1800 1801
78. T. Ogata, and J.F. Hartwig J. Am. Chem. Soc. 130 2008 13848 13849
79. W. Cabri, S. De Bernardinis, F. Francalanci, S. Penco, and R. Santi J. Org. Chem. 55 1990 350 353
80. F. Bell J. Chem. Soc. 1930 1981 1987