Regio- and stereoselective synthesis of spiro[1-benzothiepine-4(5H), 3′(3H)-pyrazol]-5-ones

Journal of Heterocyclic Chemistry

Volumn 43, Issue 6, 2006, Pages 1549-1556

  Mishriky, Nawal ^a   Girgis, Adel S ^a   Hosni, Hanaa M ^a   Farag, Hanaa ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZEPINE DERIVATIVE; NITRILIMINE DERIVATIVE; SPIRO[1 BENZOTHIEPINE 4(5H),3'(3H) PYRAZOL] 5 ONE DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; HALOGENATION; ISOMERISM; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 33845385803     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430618     Document Type: Article

References (51)

1. A. S. Shawali, Chem. Rev., 93, 2731 (1993).
2. L. De Benassuti, L. Garanti and G. Molteni, Tetrahedron: Asymmetry, 15, 1127 (2004).
3. A. F. Jalbout, Z. Jiang, H. Abou-Rachid and N. N. Benkaddour, Spectrochimica Acta Part A, 60, 603 (2004).
4. A. M. Farag, N. A. Kheder and M. Budesinsky, Tetrahedron, 53, 9293 (1997).
5. A. M. Farag, A. S. Shawali, N. M. Abed and K. M. Dawood, Gazz. Chim. Ital., 123, 467 (1993).
6. G. Meazza and G. Zanardi, J. Fluor. Chem., 67, 183 (1994).
7. P. Dalla Croce, C. La Rosa and G. Zecchi, J. Chem. Soc. Perkin Trans. 1, 2621 (1985).
8. B. Alcaide, G. Escobar, R. Perez-Ossorio and J. Plumet, An. Quim., Ser. C, 81, 85 (1985),
9. Chem. Abstr., 106, 196329 (1987).
10. G. Molteni and A. Ponti, Tetrahedron, 59, 5225 (2003).
11. A. Padwa, S. P. Craig, U. Chiacchio and D. N. Kline, J. Org. Chem., 53, 2232 (1988).
12. G. Molteni, G. Broggini and T. Pilati, Tetrahedron: Asymmetry, 13, 2491 (2002).
13. A. S. Shawali, R. H. Hilal and S. El-Sheikh, Monatsh. Chem., 132, 715 (2001).
14. N. M. Elwan, H. A. Abdelhadi, T. A. Abdallah and H. M. Hassaneen, Tetrahedron, 52, 3451 (1996).
15. K. J. Koeller and S. J. Tremont (G. D. Searle LLC, USA) PCT Int. Appl. WO 03 40,127 (C1. C07D337/00), 15 May 2003, Chem. Abstr., 138, 385315 (2003).
16. B. T. Keller, S. J. Tremont, K. C. Glenn and R. E. Manning (Pharmacia Corporation, USA) PCT Int. Appl. WO 01 68,096 (C1. A61K31/495), 20 Sep. 2001, Chem. Abstr., 135, 257253 (2001).
17. B. T. Keller, K. C. Glenn and R. E. Manning (G. D. Searle & Co., USA) U. S. US 6,268,392 (C1. 514-431, A61K31/38), 31 Jul. 2001, Chem. Abstr., 135, 137410 (2001).
18. L. F. Lee, S. C. Banerjee, H. C. Huang, J. J. Li, R. E. Miller, D. B. Reitz and S. J. Tremont (G. D. Searle & Co., USA) U. S. US 6,107,494 (C1. 549-9; C0D337/00), 22 Aug. 2000, Chem. Abstr., 133, 193089 (2000).
19. D. B. Reitz, L. F. Lee, J. J. Li, H. C. Huang, S. J. Tremont, R. E. Miller, S. C. Baneriee, R. E. Manning, K. C. Glenn and B. T. Keller (G. D. Searle & Co.; et al., USA) PCT Int. Appl. WO 98 40,375 (C1. C0D337/00), 17 Sep. 1998, Chem. Abstr., 129, 260353 (1998).
20. D. B. Reitz, L. F. Lee, J. J. Li, H. C. Huang, S. J. Tremont, R. E. Miller and S. C. Banerjee (G. D. Searle & Co.; Reitz, D. B.; Lee, L. F.; Li, J. J.; Huang, H. C.; Tremont, S. J.; Miller, R. E.; Banerjee, S. C., USA) PCT Int. Appl. WO 97 33,882 (C1. C07D337/08), 18 Sep. 1997, Chem. Abstr., 127, 307312 (1997).
21. L. F. Lee, R. E. Miller and S. J. Tremont (Monsanto Co., USA) PCT Int. Appl. WO 96 08,484 (C1. C07D337/08), 21 Mar. 1996, Chem. Abstr., 125, 114515 (1996).
22. I. Gil-Ad and A. Weizman (Ramot University Authority for Applied Research & Industrial Development Ltd., Israel) PCT Int. Appl. WO 02 43,652 (C1. A61K), 6 Jun. 2002, Chem. Abstr., 136, 395953 (2002).
23. Y. Sugita, H. Hosoya, K. Terasawa, I. Yokoe, S. Fujisawa and H. Sakagami, Anticancer Research, 21, 2629 (2001).
24. M. Shiraishi, M. Baba, M. Seto, N. Kanzaki and O. Nishimura (Takeda Chemical Industries, Ltd., Japan) PCT Int. Appl. WO 00 68,203 (C1. C07D217/06), 16 Nov. 2000, Chem. Abstr., 133, 362714 (2000).
25. Y. Aramaki, M. Seto, T. Okawa, T. Oda, N. Kanzaki and M. Shiraishi, Chem. Pharm. Bull., 52, 254 (2004).
26. M. Seto, Y. Aramaki, T. Okawa, N. Miyamoto, K. Aikawa, N. Kanzaki, S. I. Niwa, Y. Iizawa, M. Baba and M. Shiraishi, Chem. Pharm. Bull., 52, 577 (2004).
27. J. L. Roba, C. L. Gillet, M. F. Rafferty, B. Jarrot and P. M. Beart (Searle G. D. & Co.) PCT Int. Appl. WO 92 03,131 (C1. A61K31/38), 5 Mar. 1992, Chem. Abstr., 117, 20523 (1992).
28. A. Kanehira, N. Kai, S. Morie, K. Hino, K. Kawashima, I. Shimizu and K. Akiyama (Dainippon Pharmaceutical Co., Ltd., Japan) Jpn. Kokai Tokkyo Koho JP 11 302,267 (99 302,267)(C1. C07D295/02), 2 Nov. 1999, Chem. Abstr., 131, 310557 (1999).
29. S. Tsucha, Y. Miura and N. Takenawa (Tokyo Tanaba Co., Japan) Jpn. Kokai Tokkyo Koho JP 08,258,558 (96,259,558)(C1. C07D313/08), 8 Oct. 1996, Chem. Abstr., 126, 47120 (1997).
30. T. S. Jeong, K. S. Kim, S. J. An, K. H. Cho, S. Lee and W. S. Lee, Bioorg. & Med. Chem. Lett., 14, 2715 (2004).
31. T. S. Jeong, K. S. Kim, J. R. Kim, K. H. Cho, S. Lee and W. S. Lee, Bioorg. & Med. Chem. Lett., 14, 2719 (2004).
32. Y. R. Prasad, A. L. Rao, L. Prasoona, K. Murali and P. R. Kumar, Bioorg. & Med. Chem. Lett., 15, 5030 (2005).
33. E. Palaska, M. Aytemir, I. T. Uzbay and D. Erol, Eur. J. Med. Chem., 36, 539 (2001).
34. E. Palaska, D. Erol and R. Demirdamar, Eur. J. Med. Chem., 31, 43 (1996).
35. A. A. Bilgin, E. Palaska, R. Sunal and B. Gümüsel, Pharmazie, 49, 67 (1994).
36. N. Soni, K. Pande, R. Kalsi, T. K. Gupta, S. S. Parmar and J. P. Barthwal, Res. Commun. Chem. Pathol. Pharm., 56, 129 (1987).
37. S. S. Parmar, B. R. Pandey, C. Dwivedi and R. D. Harbison, J. Pharm. Sci., 63, 1152 (1974).
38. M. I. Ali, M. A. F. El-Kaschef and A. G. Hammam, J. Prakt. Chem., 316, 259 (1974).
39. V. D. Orlov, E. I. Mikhed'kina and V. F. Lavrushin, Zh. Obshch. Khim., 52, 126 (1982),
40. Chem. Abstr., 96, 142680 (1982).
41. V. J. Traynelis and R. F. Love, J. Org. Chem., 26, 2728 (1961).
42. T. Fathi, K. Ciamala, N. Dinh An and J. Vebrel, Can. J. Chem., 72, 1424 (1994).
43. A. S. Girgis, Y. A. Ibrahim, N. Mishriky, J. N. Lisgarten, B. S. Potter and R. A. Palmer, Tetrahedron, 57, 2015 (2001).
44. H. M. Hassaneen, R. H. Hilal, N. M. Elwan, A. Harhash and A. S. Shawali, J. Heterocycl. Chem., 21, 1013 (1984).
45. A. S. Girgis, Z. Naturforsch., 55b, 222 (2000).
46. R. Raghunathan, M. Shanmugasundaram, S. Bhanumathi and P. J. E. Malar, Heteroat. Chem. 9, 327 (1998).
47. R. Huisgen, M. Seidel, G. Wallbillich and H. Knupfer, Tetrahedron, 17, 3 (1962).
48. A. F. Hegarty, J. A. Kearney and F. L. Scott, J. Chem. Soc. Perkin Trans. 2, 1422 (1973).
49. Full crystallographic details of compounds 5a,f,g, excluding structure factors, have been deposited at Cambridge Crystallographic Data Centre (CCDC) as supplementary publication numbers CCDC 608042, CCDC 608040 and CCDC 608041, respectively.
50. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, J. Appl. Cryst., 27, 435 (1994).
51. S. Mackay, C. J. Gilmore, C. Edwards, N. Stewart and K. Shankland, maXus Computer Program for the Solution and Refinement of Crystal Structures, Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow (1999).