Magnesium perchlorate as a new and highly efficient catalyst for the synthesis of 2,3-dihydro-1,5-benzothiazepines

Synthesis

Volumn , Issue 4, 2007, Pages 541-546

  Khatik, Gopal L ^a   Kumar, Raj ^a   Chakraborti, Asit K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

1,3 diarylprop 2 enones; 1,5 benzothiazepines; 2 aminothiophenol; Catalyst; Chemoselective; Magnesium perchlorate

Indexed keywords

1,3-DIARYLPROP-2-ENONES; 1,5-BENZOTHIAZEPINES; 2-AMINOTHIOPHENOL; CHEMOSELECTIVE;

AROMATIC COMPOUNDS; CATALYSTS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

MAGNESIUM COMPOUNDS;

2,3 DIHYDRO 1,5 BENZOTHIAZEPINE DERIVATIVE; BENZOTHIAZEPINE DERIVATIVE; MAGNESIUM PERCHLORATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 33947543295     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965892     Document Type: Article

References (53)

1. Sarro, G. D.; Chimirri, A.; Sarro, A. D.; Gitto, R.; Grasso, S.; Zappalá, M. Eur. J. Med. Chem. 1995, 30, 925.
2. (a) Shinichi, Y.; Yoshikazu, M.; Katsuji, M.; Yoshinori, I.; Yasuhiko, O.; Ryuzo, Y.; Tadashi, N.; Hiroyasu, S. J. Org. Chem. 1996, 61, 8586.
3. (b) Kurokawa, J.; Adachi-Akahane, S.; Nagao, T. Eur. J. Pharmacol. 1997, 325, 229.
4. Miyata, O.; Tetsuro, S.; Ichiya, N.; Takeaki, N. Tetrahedron 1997, 53, 2421.
5. Grandolini, G.; Perioli, L.; Ambrogi, V. Eur. J. Med. Chem. 1999, 34, 701.
6. Yang, X.; Buzon, L.; Hamanaka, E.; Liu, K. K.-C. Tetrahedron: Asymmetry 2000, 11, 4447.
7. Urbanski, M. J.; Chen, R. H.; Demarest, K. T.; Gunnet, J.; Look, R.; Ericson, E.; Murray, W. V.; Rybczynski, P. J.; Zhang, X. Bioorg. Med. Chem. Lett. 2003, 13, 4031.
8. Di Santo, R.; Costi, R. Farmaco 2005, 60, 385.
9. Lévai, A. J. Heterocycl. Chem. 2000, 37, 199.
10. Kodomari, M.; Noguchi, T.; Aoyama, T. Synth. Commun. 2004, 34, 1783.
11. Patel, V. M.; Desai, K. R. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43, 199.
12. (a) Lévai, A. J. Heterocycl. Chem. 2004, 41, 399.
13. (b) Lévai, A. J. Heterocycl. Commun. 2002, 8, 227.
14. (c) Lévai, A. J. Heterocycl. Commun. 2002, 8, 375.
15. Micheli, F.; Degiorgis, F.; Feriani, A.; Paio, A.; Pozzan, A.; Zarantonello, P.; Seneci, P. J. Comb. Chem. 2001, 3, 224.
16. Pant, S.; Singhal, B.; Upreti, M.; Pant, U. Molecules 1998, 3, 159.
17. (a) Upreti, M.; Pant, S.; Dandia, A.; Pant, U. C. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1997, 36, 1181.
18. (b) Pant, S.; Sharma, A.; Sharma, S. K.; Pant, U. C.; Goel, A. K. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1996, 35, 794.
19. Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V.; Forood, B.; Flatt, B.; Nakai, H. J. Heterocycl. Chem. 2000, 37, 1655.
20. Dandia, A.; Sati, M.; Loupy, A. Green Chem. 2002, 4, 599.
21. Patel, V. M.; Desai, K. R. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43, 199.
22. Olah, G. A.; Prakash, G. K. S.; Sommer, J. Superacids; Wiley: New York, 1985.
23. (a) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
24. (b) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
25. Dumeunier, R.; Markó, I. E. Tetrahedron Lett. 2004, 45, 825.
26. Orita, A.; Tanahashi, C.; Kakuda, A.; Otera, J. J. Org. Chem. 2001, 66, 8926.
27. Qian, C.; Huang, T. J. Org. Chem. 1998, 63, 4125.
28. Foropoulos, J.; DesMarteau, D. D. Inorg. Chem. 1984, 23, 3720.
29. Chakraborti, A. K.; Shivani, J. Org. Chem. 2006, 71, 5785; and references cited therein.
30. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265.
31. Thia-Michael addition: (a) Garg, S. K.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2005, 46, 1721.
32. (b) Garg, S. K.; Kumar, R.; Chakraborti, A. K. Synlett 2005, 1370.
33. Acylation: (c) Chakraborti, A. K.; Sharma, L.; Gulhane, R.; Shivani, Tetrahedron 2003, 59, 7661.
34. (d) Chakraborti, A. K.; Gulhane, R.; Shivani, Synlett 2003, 1805.
35. Imine formation: (e) Chakraborti, A. K.; Bhagat, S.; Rudrawar, S. Tetrahedron Lett. 2004, 45, 7641.
36. Acylal formation: (f) Kumar, R.; Thilagavathi, R.; Gulhane, R.; Chakraborti, A. K. J. Mol. Catal. A: Chem. 2006, 250, 227.
37. Cogolli, P.; Maiolo, F.; Testaferri, L.; Tingoli, M.; Tiecco, M. J. Org. Chem. 1979, 44, 2642.
38. Cogolli, P.; Testaferri, L.; Tingoli, M.; Tiecco, M. J. Org. Chem. 1979, 44, 2636.
39. (a) Hwu, J. R.; Wong, F. F.; Shiao, M.-J. J. Org. Chem. 1992, 57, 5254.
40. (b) Shiao, M.-J.; Lai, L.-L.; Ku, W.-S.; Lin, P.-Y.; Hwu, J. R. J. Org. Chem. 1993, 58, 4742.
41. (a) Katritzky, I.; Takahashi, I.; Marson, C. M. J. Org. Chem. 1986, 51, 4914.
42. (b) Belley, M.; Zamboni, R. J. Org. Chem. 1989, 54, 1230.
43. (a) Hilhorst, E.; Chen, T. B. R. A.; Iskander, A. S.; Pandit, U. K. Tetrahedron 1994, 50, 7837.
44. (b) Surdhar, P. S.; Armstrong, D. A. J. Phys. Chem. 1986, 90, 5915.
45. (c) Ashby, E. C.; Park, W.-S.; Goel, A. B.; Su, W. Y. J. Org. Chem. 1985, 50, 5184.
46. (a) Gavande, N. S.; Kundu, S.; Badgujar, N. S.; Kaur, G.; Chakraborti, A. K. Tetrahedron 2006, 62, 4201.
47. (b) Chakraborti, A. K.; Sharma, L.; Nayak, M. K. J. Org. Chem. 2002, 67, 6406.
48. (c) Chakraborti, A. K.; Sharma, L.; Nayak, M. K. J. Org. Chem. 2002, 67, 2541.
49. (d) Chakraborti, A. K.; Nayak, M. K.; Sharma, L. J. Org. Chem. 2002, 67, 1776.
50. (e) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
51. Chakraborti, A. K.; Nayak, M. K.; Sharma, L. J. Org. Chem. 1999, 64, 8027.
52. (a) Sharma, L.; Nayak, M. K.; Chakraborti, A. K. Tetrahedron 1999, 55, 9595.
53. (b) Nayak, M. K.; Chakraborti, A. K. Chem. Lett. 1998, 297.