Synthesis of sulfonamides and 1,3-Oxazine-2,4-diones from arylsulfonyl isocyanates and diketene

Synthesis

Volumn , Issue 13, 2008, Pages 2073-2076

  Alizadeh, Abdolali ^c   Zohreh, Nasrin ^a   Zhu, Long Guan ^b  

^a TARBIAT MODARES UNIVERSITY   (Iran)

^b ZHEJIANG UNIVERSITY   (China)

^c NONE

Author keywords

Arylsulfonyl isocyanate; Catalytic reaction; Diketene; N heteroaromatic compounds; Sulfonamides; Zwitterions

Indexed keywords

AMIDES; SULFUR COMPOUNDS;

FUNCTIONALIZED; SULFONAMIDES (SA);

NITROGEN COMPOUNDS;

6 METHYL 3 (PHENYLSULFONYL) 2H 1,3 OXAZINE 2,4 (3H)DIONE; 6 METHYL 3 [(METHYLPHENYL)SULFONYL] 2H 1,3 OXAZINE 2,4 (3H)DIONE; [(2,6 DIMETHYL 4 OXO 4H PYRAN 3 YL)CARBONYL] 1 BENZENESULFONAMIDE; [(2,6 DIMETHYL 4 OXO 4H PYRAN 3 YL)CARBONYL] 4 METHYL 1 BENZENESULFONAMIDE; ISOCYANIC ACID DERIVATIVE; OXAZINE DERIVATIVE; PYRIDINE; SULFONAMIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENVIRONMENTAL TEMPERATURE; SYNTHESIS;

EID: 47349084060     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067115     Document Type: Article

References (70)

1. Navia, M. A. Science 2000, 288, 2132.
2. Mohamed,S. K. Afinidad 2000, 57, 451
3. Chem.Abstr. 2000, 133, 73818x.
4. Maren, T. H.; Conroy, C. W. J. Biol. Chem. 1993, 268, 26233.
5. Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C. T. Curr. Med. Chem. 2003, 10, 925.
6. Owa, T.; Yoshino, H.; Okauchi, T.; Yoshimatsu, K.; Ozawa, Y.; Sugi, N. H.; Nagasu, T.; Koyanagi, N.; Kitoh, K. J. Med. Chem. 1999, 42, 3789.
7. Koyanagi, N.; Nagasu, T.; Fujita, F.; Watanabe, T.; Tsukahara, K.; Funahashi, Y.; Fujita, M.; Taguchi, T.; Yoshino, H.; Kitoh, K. Cancer Res. 1994, 54, 1702.
8. (a) Roush, W. R.; Gwaltney, S. L.; Cheng, J.; Scheidt, K. A.; McKerrow, J. H.; Hanseil, E. J. Am. Chem. Soc. 1998, 120, 10994.
9. (b) Roush, W. R.; Cheng, J.; Knapp-Reed, B.; Alvarez-Hernandez, A.; McKerrow, J. H.; Hanseil, E.; Engel, J. C. Bioorg. Med. Chem. Lett. 2001, 11, 2759.
10. (c) Maren, T. H. Annu. Rev. Pharmacol. Toxicol. 1976, 16, 309.
11. (d) Supuran, C. T.; Briganti, F.; Tilli, S.; Chegwidden, W. R.; Scozzafava, A. Bioorg. Med. Chem. 2001, 9, 703.
12. (e) Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. J. Med. Chem. 2000, 43, 4542.
13. (a) Yokoi, A.; Kuromitsu, J.; Kawai, T.; Nagasu, T.; Sugi, N. H.; Yoshimatsu, K.; Yoshino, H.; Owa, T. Mol. Cancer Ther. 2002, 1, 275.
14. (b) Oda, Y.; Owa, T.; Sato, T.; Boucher, B.; Daniels, S.; Yamanaka, H.; Shinohara, Y.; Yokoi, A.; Kuromitsu, J.; Nagasu, T. Anal. Chem. 2003, 75, 2159.
15. (c) Owa, T.; Yokoi, A.; Yamazaki, K.; Yoshimatsu, K.; Yamori, T.; Nagasu, T. J. Med. Chem. 2002, 45, 4913.
16. (d) Owa, T.; Okauchi, T.; Yoshimatsu, K.; Sugi, N. H.; Ozawa, Y.; Nagasu, T.; Koyanagi, N.; Okabe, T.; Kitoh, K.; Yoshino, H. Bioorg. Med. Chem. Lett. 2000, 10, 1223.
17. Huang, S.; Connolly, P. J.; Lin, R.; Emanuel, S.; Middleton, S. A. Bioorg. Med. Chem. Lett. 2006, 16, 3639.
18. (a) Staunton, J. In Comprehensive Organic Chemistry, Vol. 4; Barton, D. H. R.; Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979, 679.
19. (b) See also: Staunton, J. In Comprehensive Organic Chemistry, Vol. 4; Barton, D. H. R.; Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979, 688.
20. (a) See also: Ellis, G. P. In The Chemistry of Heterocyclic Compounds Chromenes, Chromanones and Chromones, Vol. 31; Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1977, 912.
21. (b) Ellis, G. P. In The Chemistry of Heterocyclic Compounds Chromenes, Chromanones and Chromones, Vol. 31; Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1977, 985.
22. (c) Ellis, G. P. In The Chemistry of Heterocyclic Compounds Chromenes, Chromanones and Chromones, Vol. 31; Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1977, 1063.
23. (a) Kato, Y. Food Sci. Technol. Res. 2003, 9, 264.
24. (b) Yanagimoto, K.; Ochi, H.; Lee, K. G.; Shibamoto, T. J. Agric. Food Chem. 2004, 52, 592.
25. (a) Caravan, P.; Gelmini, L.; Glover, N.; Herring, F. G.; McNeill, H.; Li, J. H.; Rettig, S. J.; Setyawati, I. A.; Shuter, E.; Sun, Y.; Tracey, A. S.; Yuen, V. G.; Orvig, C. J. Am. Chem. Soc. 1995, 117, 12759.
26. (b) Reffitt, D. M.; Burden, T. J.; Seed, P. T.; Wood, J.; Thompson, R. P. H.; Powell, J. J. Ann. Clin. Biochem. 2000, 37, 457.
27. (c) Johnson, V. J.; Sharma, R. P. Neurotoxicology 2003, 24, 261.
28. (d) Hinds, F. E.; Aldrich-Wright, J. R.; Leverett, P.; Hazell, S.L. J. Inorg. Biochem. 2003, 96, 144.
29. (e) Ellis, B. L.; Duhme, A. K.; Hider, R. C.; Hossian, M. B.; Rizvi, S.; van der Helm, D. J. Med. Chem. 1996, 39, 3659.
30. (a) Clauson-Kaas, N.; Denss, R.; Ostermayer, F.; Renk, E. J. R. Geigy A.G., Swiss Appl. 1339175, 1961; Chem. Abstr. 1964, 60, 4158d.
31. (b) Clauson-Kaas, N.; Denss, R.; Ostermayer, F.; Renk, E. J. R. Geigy A.G. Swiss Appl. 419160, 1967;
32. Chem. Abstr. 1967, 66, 115718v.
33. (a) Coppola, G. M. Synthesis 1980, 503.
34. (b) Coppola, G. M.; Marsden, C. M. Heterocycl. Commun. 1996, 2, 301.
35. (a) Kawai, M.; BaMaung, N. Y.; Fidanze, S. D.; Erickson, S. A.; Tedrow, J. S.; Sanders, W. J.; Vasudevan, A.; Park, C.; Hutchins, C.; Comess, K. M.; Kalvin, D.; Wang, J.; Zhang, Q.; Lou, P.; Tucker-Garcia, L.; Bouska, J.; Bell, R. L.; Lesniewski, R.; Henkin, J.; Sheppard, G. S. Bioorg. Med. Chem. Lett. 2006, 16, 3574.
36. (b) Siddiqui,N.;Pandeya, S.N. Bioorg. Med. Chem. Lett. 2007, 17, 255.
37. (c) Johnson, D. C.; Widlanski, T. S. Tetrahedron Lett. 2001, 42, 3677.
38. (d) Vogel, A. Textbook of Practical Organic Chemistry; Longman: London, 1978, 4th ed., 647
39. (e) Cremlyn, R. Organosulfur Chemistry: An Introduction; Wiley: New York, 1996.
40. (f) Anderson, K. K. Sulfonic Acids and Their Derivatives, In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R.; Ollis, W. D.; Jones, D. N., Eds.; Pergamon Press: Oxford, 1979.
41. (g) Domínguez, J. N.; León, C.; Rodrigues, J.; Domínguez, N.; Gut, J.; Rosenthal, P. Farmaco 2005, 60, 307.
42. (h) Murakami, Y.; Kondo, K.; Sekimoto, E.; Nakao, J. Tetrahedron 2000, 56, 5843.
43. (i) Ito, Y.; Manabe, S.; Sugioka, T. Tetrahedron Lett. 2007, 48, 787.
44. (j) Alizadeh, A.; Rostamnia, S.; Esmaili, A. Synthesis 2007, 709.
45. (a) Bartol, G.; Bosco, M.; Cimarreli, C.; Dalpozo, R.; Guereio, G.; Palmieri, G. J. Chem. Soc., Perkin Trans. 1 1993, 2081.
46. (b) Yamamoto, Y.; Morita, Y. Chem. Pharm. Bull. 1984, 32, 2957.
47. (c) Majetich, G.; Zhanj, Y.; Dreger, G. Tetrahedron Lett. 1993, 34, 449.
48. (d) Ficini, J.; Pouliquen, J. Tetrahedron Lett. 1972, 1135.
49. (e) Sano, T.; Saitoh, T. Heterocycles 1993, 36, 2139.
50. (f) Kim, H. S.; Yoon, Y. H. Bull. Korean Chem. Soc. 1993, 14, 159.
51. (g) Andrey Chicov, Y. S.; Vinokurova, O. V.; Gein, V. L. Chem. Heterocycl. Compd. (English Trans.) 1989, 126.
52. (h) Weeks, P. D.; Brennan, T. M.; Brannegan, T. D.; Kuhla, D. E.; Elliott, M. L.; Watson, H. A. J. Org. Chem. 1980, 45, 1109.
53. (i) Grrige, R; Jachson, G. L. J. Chem. Soc. C 1970, 552.
54. (j) Harris, T. M.; Wachter, M. P. Tetrahedron 1970, 26, 5255.
55. (a) Clauson-Kaas, N.; Denss, R.; Ostermayer, F.; Renk, E. J. R. Geigy A.G., Swiss Appl. 436323, 1968; Chem. Abstr. 1968, 69, 27435g.
56. (b) Clauson-Kaas, N.; Denss, R.; Ostermayer, F.; Renk, E. J. R. Geigy A.G., Swiss Appl. 412 602, 1967; Chem. Abstr. 1967, 67: 11492w.
57. Huisgen, R.; Herbig, K.; Morikawa, M. Chem. Ber. 1967, 100, 1107.
58. Ulrich, H. Chem. Rev. 1962, 2, 186.
59. Adib, M.; Yavari, H.; Mollahosseini, M. Tetrahedron Lett. 2004, 45, 1803.
60. Ozaki, S. h. Chem. Rev. 1972, 72, 457.
61. Alizadeh, A.; Zohreh, N.; Rostamnia, S. Tetrahedron 2007, 63, 8083.
62. Mansson, M.; Nakase, Y.; Sunner, S. Acta Chem. Scand. 1968, 22, 171.
63. Briody, J. M.; Satchell, D. P. N. J. Chem. Soc. 1965, 3778.
64. Briody, J. M.; Satchell, D. P. N. Chem. Ind. (London) 1964, 893.
65. Eck, H. Wacker Chemie GmbH, Br. Patent 1346701, 1974s; Chem. Abstr. 1973, 79, 18109.
66. Marcus, E.; Chan, J. K.; Strow, C. B. J. Org. Chem. 1966, 31, 1369.
67. (a) Pochan, M. Lonza Ltd., Swiss Patent 523223, 1972; Chem. Abstr. 1972, 77, 100857.
68. (b) Stocker, A. Lonza, US Patent 3778474, 1973; Chem. Abstr. 1974, 80, 59503.
69. (c) Künstle, G.; Spes, H.; Siegl, H. Wacker-Chemie GmbH, U.S. Patent 4129596, 1978; Chem. Abstr. 1978, 89, 42479f.
70. Crystallographic data for 5a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 642465. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).