Synthesis of diazaheterocyclic ring-fused 1,2,4-benzothiadiazine 1,1-dioxides by a sequential aza-Wittig/NH-addition cyclization/nucleophilic ring-closure methodology with N-alkenyl-2-carbodiimidobenzenesulfonamides as key intermediates

European Journal of Organic Chemistry

Volumn , Issue 12, 2008, Pages 2075-2083

  Hirota, Shinsuke ^a   Kato, Ryo ^a   Suzuki, Madoka ^a   Soneta, Yuji ^a   Otani, Takashi ^a   Saito, Takao ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

1,2,4 Benzothiadiazine 1,1 dioxides; Carbodiimides; Fused ring systems; Nitrogen heterocycles; Tandem reactions

Indexed keywords

EID: 53749087798     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701131     Document Type: Article

References (88)

1. a) R. G. d. S. Berlinck, Fortschr. Chem. Org. Naturst. 1995, 66, 119-295;
2. b) R. G. S. Berlinck, Nat. Prod. Rep. 1996, 13, 377-409;
3. c) R. G. S. Berlinck, Nat. Prod. Rep. 1999, 16, 339-365;
4. d) R. G. S. Berlinck, Nat. Prod. Rep. 2002, 19, 617-649;
5. e) R. G. S. Berlinck, M. H. Kossuga, Nat. Prod. Rep. 2005, 22, 516-550;
6. f) L. Heys, C. G. Moore, P. J. Murphy, Chem. Soc. Rev. 2000, 29, 57-67.
7. Monocyclic guanidines; a) P. Molina, M. Alajarin, J. R. Saez, Synthesis 1984, 983-986;
8. b) P. Molina, M. Alajarin, J. R. Saez, M. d. l. C. Foces-Foces, F. H. Cano, R. M. Claramunt, J. Elguero, J. Chem. Soc. Perkin Trans. 1 1986, 2037-2049;
9. c) P. Molina, P. Almendros, P. M. Fresneda, Tetrahedron Lett. 1994, 35, 2235-2236;
10. d) P. Molina, P. M. Fresneda, M. A. Sanz, J. Org. Chem. 1999, 64, 2540-2544;
11. e) P. Molina, P. M. Fresneda, S. Delgado, J. A. Bleda, Tetrahedron Lett. 2002, 43, 1005-1007.
12. Bicyclic guanidines; f) P. Molina, M. Alajarin, A. Vidal, J. Chem. Soc. Chem. Commun. 1992, 295-296;
13. g) P. Molina, A. Arques, A. Alias, M. C. Foces-Foces, A. L. Llamas-Saiz, J. Chem. Soc. Chem. Commun. 1992, 424-426;
14. h) P. Molina, M. Alajarin, A. Vidal, J. Org. Chem. 1992, 57, 6703-6711;
15. i) P. Molina, A. Arques, A. Alias, J. Org. Chem. 1993, 58, 5264-5270;
16. j) F. Oton, A. Tarraga, A. Espinosa, M. D. Velasco, D. Bautista, P. Molina, J. Org. Chem. 2005, 70, 6603-6608.
17. Monocyclic guanidines: a) H. Wamhoff, G. Haffmanns, Chem. Ber. 1984, 117, 585-621;
18. b) A. Csampai, G. Turos, V. Kudar, K. Simon, H. Oeynhausen, H. Wamhoff, P. Sohar, Eur. J. Org. Chem. 2004, 717-723.
19. Bicyclic guanidines: c) H. Wamhoff, G. Hendrikx, Chem. Ber. 1985, 118, 863-872;
20. d) G. Turos, A. Csampai, T. Lovasz, A. Gyorfi, H. Wamhoff, P. Sohar, Eur. J. Org. Chem. 2002, 3801-3806.
21. Monocyclic guanidines: a) M.-W. Ding, H.-Y. Tu, Z.-J. Liu, Synth. Commun. 1997, 27, 3657-3662;
22. b) M.-W. Ding, S.-Z. Xu, J.-F. Zhao, J. Org. Chem. 2004, 69, 8366-8371;
23. c) S. Z. Xu, M. H. Cao, M. W. Ding, H. W. He, Chin. Chem. Lett. 2005, 16, 1177-1180;
24. d) J.-C. Liu, H.-W. He, Q.-Y. Ren, M.-W. Ding, Helv. Chim. Acta 2006, 89, 1337-1343.
25. Bicyclic guanidines: e) M.-W. Ding, N.-Y. Huang, H.-W. He, Synthesis 2005, 1601-1604.
26. Monocyclic guanidines: a) C. Peinador, M. J. Moreira, J. M. Quintela, Tetrahedron 1994, 50, 6705-6714;
27. b) J. M. Quintela, R. Alvarez-Sarandes, C. Peinador, Tetrahedron 1998, 54, 8107-8122;
28. c) D. V. Vilarelle, C. P. Veira, J. M. Quintela Lopez, , Tetrahedron 2004, 60, 275-283.
29. Bicyclic guanidines; a) T. Okawa, S. Eguichi, A. Kakehi, J. Chem. Soc. Perkin Trans. 1 1996, 247-254;
30. b) T. Okawa, M. Kawase, S. Eguchi, A. Kakehi, M. Shiro, J. Chem. Soc. Perkin Trans. 1 1998, 2277-2285.
31. Monocyclic guanidines: a) Y. Isomura, S. Yamasaki, H. Okada, M. Noguchi, Heterocycl. Commun. 1995, 1, 421-426.
32. Bicyclic guanidines: b) M. Noguchi, H. Okada, M. Watanabe, H. Moriyama, O. Nakamura, A. Kakehi, Heterocycl. Commun. 1996, 2, 361-370;
33. c) M. Watanabe, H. Okada, T. Teshima, M. Noguchi, A. Kakehi, Tetrahedron 1996, 52, 2827-2838;
34. d) M. Noguchi, H. Okada, M. Watanabe, K. Okuda, O. Nakamura, Tetrahedron 1996, 52, 6581-6590.
35. Monocyclic guanidines: a) M. Nitta, T. Morito, Y. Mitsumoto, S. Naya, Heterocycles 2005, 65, 1629-1639;
36. b) M. Nitta, D. Ohtsuki, Y. Mitsumoto, S. Naya, Tetrahedron 2005, 61, 6073-6081.
37. Monocyclic guanidines: a) K. Nagamatsu, H. Fujii, N. Abe, A. Kakehi, Heterocycles 2004, 64, 291-303;
38. b) K. Nagamatsu, A. Serita, J.-H. Zeng, H. Fujii, N. Abe, A. Kakehi, Heterocycles 2006, 67, 337-351.
39. Bicyclic guanidines; c) K. Nagamatsu, E. Akiyoshi, H. Ito, H. Fujii, A. Kakehi, N. Abe, Heterocycles 2006, 69, 167-178.
40. Monocyclic guanidines: a) T. Saito, K. Tsuda, Y. Saito, Tetrahedron Lett. 1996, 37, 209-212;
41. b) T. Saito, T. Ohkubo, H. Kuboki, M. Maeda, K. Tsuda, T. Karakasa, S. Satsumabayashi, J. Chem. Soc. Perkin Trans. 1 1998, 3065-3080.
42. Bicyclic guanidines: c) T. Saito, K. Tsuda, Tetrahedron Lett. 1996, 37, 9071-9072.
43. a) P. Molina, M. J. Vilaplana, Synthesis 1994, 1197-1218;
44. b) P. M. Fresneda, P. Molina, Synlett 2004, 1-17;
45. c) S. Eguchi, ARKIVOC 2005, II, 98-119;
46. d) S. Braese, C. Gil, K. Kneppwer, V. Zimmermann, Angew. Chem. Int. Ed. 2005, 44, 5188-5240;
47. e) S. Eguchi, Top. Heterocycl. Chem. 2006, 6, 113-156;
48. f) F. Palacios, C. Alonso, D. Aparicio, G. Rubiales, J. M. de los Santos, Tetrahedron 2007, 63, 523-575.
49. [11].
50. a) M. A. Arnold, S. G. Duron, D. Y. Gin, J. Am. Chem. Soc. 2005, 127, 6924-6925;
51. b) M. A. Arnold, K. A. Day, S. G. Duron, D. Y. Gin, J. Am. Chem. Soc. 2006, 128, 13255-13260.
52. a) P. de Tullio, R. Ouedraogo, L. Dupont, F. Somers, S. Boverie, J.-M. Dogne, J. Delarge, B. Pirotte, Tetrahedron 1999, 55, 5419-5432;
53. b) P. de Tullio, B. Pirotte, P. Lebrun, J. Fontaine, L. Dupont, M.-H. Antoine, R. Ouedraogo, S. Khlelili, C. Maggetto, B. Masereel, O. Diouf, T. Podona, J. Delarge, J. Med. Chem. Lett. 1996, 39, 937-948;
54. c) P. de Tullio, B. Becker, S. Boverie, M. Dabrowski, P. Wahl, M.-H. Antoine, F. Somers, S. Sebille, R. Ouedraogo, J. B. Hansen, P. Lebrun, B. Pirotte, J. Med. Chem. 2003, 46, 3342-3353;
55. d) A. J. Peat, C. Townsend, J. F. Worley III, S. H. Allen, D. Garrido, R. J. Mertz, J. L. Pfohl, C. M. Terry, J. F. Traux, R. L. Veasey, S. A. Thomson, Bioorg. Med. Chem. Lett. 2002, 12, 2977-2980;
56. e) P. de Tullio, S. Boverie, B. Becker, M.-H. Antoine, Q.-A. Nguyen, P. Francotte, S. Counerotte, S. Sebille, B. Pirotte, P. Lebrun, J. Med. Chem. 2005, 48, 4990-5000.
57. R. Ouedraogo, B. Becker, S. Boverie, F. Somers, M. H. Antoine, B. Pirotte, P. Lebrun, P. de Tullio, Biol. Chem. 2002, 383, 1759-1768.
58. J. W. Chern, P. L. Tao, K. C. Wang, A. Gutcait, S. W. Liu, M. H. Yen, S. L. Chien, J. K. Rong, J. Med. Chem. 1998, 41, 3128-3141.
59. a) A. V. N. Reddy, A. Kamal, A. B. Rao, P. B. Sattur, Eur. J. Med. Chem. 1987, 22, 157-160;
60. b) J. W. Chern, C. P. Ho, Y. H. Wu, K. C. Liu, Phosphorus Sulfur Silicon Relat. Elem. 1991, 59, 529-532;
61. c) J. W. Chern, Y. C. Liaw, C. S. Chen, J. G. Rong, C. L. Huang, C. H. Chan, A. H. J. Wang, Heterocycles 1993, 36, 1091-1103;
62. d) J. W. Chern, J. G. Rong, Tetrahedron Lett. 1991, 32, 2935-2938;
63. e) J. W. Chern, C. Y. Shiau, Y. H. Wu, Synthesis 1991, 159-161;
64. f) R. Friary, E. H. Gold, Heterocycles 1977, 7, 765-771;
65. g) S. Boverie, M. H. Antoine, P. de Tullio, F. Somers, B. Becker, S. Sebille, P. Lebrun, B. Pirotte, J. Pharm. Pharmacol. 2001, 53, 973-980.
66. Syntheses of variously functionalized 3-amino-1,2,4-benzothiadiazine 1,1-dioxides 7 in solution by sequential aza-Wittig/heterocumulene annelation and further ring-forming transformation methodology have been reported; in part these include preliminary results from this paper: T. Saito, S. Hirota, M. Kitamura, M. Shiotani, T. Takahashi, Abstracts of 31st Congress of Heterocyclic Chemistry, October 2000, Kitakyushu, Japan, 2000, pp. 215-216.
67. a) P. Perlmutter, Top. Curr. Chem. 1997, 190, 87-101;
68. b) K. E. Harding, T. H. Tiner, in Comprehensive Organic Synthesis (Eds: B. M. Trost, I. Fleming), Pergamon, Oxford, U. K., 1991, vol. 4, pp. 363-421.
69. a) R. C. Larock, in Solvomercuration/Demercuration Reactions in Organic Synthesis, Springer-Verlag, Berlin, 1986;
70. b) F. Esser, Synthesis 1987, 460-466.
71. Recently, Blackburn and co-authors reported the synthesis of 3-amino-1,2,4-benzothiadiazine 1,1-dioxides through approaches involving aza-Wittig reactions on polymer-supported iminophosphorane and internal NH-addition annulation onto the resulting carbodiimide group: C. Blackburn, A. Achab, A. Elder, S. Ghosh, J. Guo, G. Harriman, M. Jones, J. Org. Chem. 2005, 70, 10206-10209.
72. P. Molina, A. Lorenzo, E. Aller, Synthesis 1992, 297-302.
73. [7c]
74. a) N. Hall, Science 1994, 266, 32-34;
75. b) T.-L. Ho in Tandem Organic Reactions, Wiley, New York, 1992;
76. c) for domino reactions: L. F. Tietze, G. Brasche, K. M. Gericke in Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006;
77. d) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
78. e) L. F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
79. f) S. E. Demmark, A. Thorarensen, Chem. Rev. 1996, 96, 137-166;
80. g) J. D. Winkler, Chem. Rev. 1996, 96, 167-176;
81. h) I. Ryu, N. Sonoda, D. P. Curran, Chem. Rev. 1996, 96, 177-194;
82. i) P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206;
83. j) for cascade processes: A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96, 223-270;
84. k) K. Neuschütz, J. Velker, R. Neier, Synthesis 1998, 227-255.
85. F. Ek, L.-G. Wistrand, T. Frejd, Tetrahedron 2003, 59, 6759-6769.
86. A. Saeed, N. H. Rama, J. Chem. Soc. Pak. 1997, 19, 236-239.
87. a) G. M. Sheldrick, SHELXS-97 - Program for the Solution of Crystal Structures, University of Göttingen, Göttingen (Germany), 1997;
88. b) G. M. Sheldrick, SHELXL-97 - Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen (Germany), 1997.