Efficient and eco-friendly syntheses of 1,5-benzothiazepines and 1,5-benzodiazepines catalyzed by [Hmim][NO3] under mild conditions

Journal of Heterocyclic Chemistry

Volumn 51, Issue 1, 2014, Pages 138-150

  Loghmani Khouzani, Hossein ^a   Tamjidi, Panteha ^a   Mohammadpoor Baltork, Iraj ^a   Yaeghoobi, Marzieh ^b   Rahman, Noorsaadah Abd ^b   Khosropour, Ahmad Reza ^a   Moghadam, Majid ^a   Tangestaninejad, Shahram ^a   Mirkhani, Valiolah ^a   Habibi, Mohammad Hossein ^a   Kashima, Ayana ^c   Suzuki, Takayoshi ^c  

^a UNIVERSITY OF ISFAHAN   (Iran)

^b UNIVERSITY OF MALAYA   (Malaysia)

^c OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84894905413     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.1827     Document Type: Article

References (65)

1. Jiaxi, X., Mol Div 2005, 9, 45.
2. Ansari, F. L.,;, Umbreen, S.,;, Hussain, L.,;, Makhmoor, T.,;, Nawaz, S.,;, Lodhi, M. A.,;, Khan, S. N.,;, Shaheen, F.,;, Choudhary, M. I.,;, Rahman, A., Chem Biodivers 2005, 2, 487.
3. Sarro, G. D.,;, Chimirri, A.,;, Sarro, A. D.,;, Gitto, R.,;, Grasso, S.,;, Zappala, M., Eur J Med Chem 1995, 30, 925.
4. Dias, J. A.,;, Vega, S.,;, Exposito, M. A.,;, Mateo, C. C. S.,;, Darias, V., Arch Pharm 1996, 329, 352.
5. Kevin, K. J.,;, Richard, C. E., J Heterocycl Chem 1993, 30, 177.
6. Bajaj, K.,;, Srivastava, V. K.,;, Lata, R.,;, Chandra, R.,;, Kumar, A., Indian J Chem 2003, 42B, 1723.
7. Bajaj, K.,;, Srivastava, V. K.,;, Kumar, A., Indian J Chem 2003, 42B, 1149.
8. Dandia, A.,;, Singh, R.,;, Khaturia, S., J Flourine Chem 2007, 128, 524.
9. Arya, K.,;, Dandia, A., Med Chem 2008, 18, 114.
10. (a), Rodriguez, R.,;, Insuasty, B.,;, Abonia, R.,;, Quiroga, J., Arkivoc 2004, xiii, 67
11. (b), Nahed, K., Can. Pat. Appl. CA 2,030,159, 1991 (Chem. Abstr. 1991, 115, 1985150f).
12. Chaffman, M.,;, Brogden, R. N., Drugs 1985, 29, 387.
13. Alonzo, D.,;, Allert, J.,;, Thomas, H.,;, Darbenzio, A.,;, Raymond, R.,;, Joseph, S. C., J Cardiovasc Pharmacol 1993, 21, 677.
14. Micheli, F.,;, Degiorgis, A.,;, Feriani, A.,;, Paio, A.,;, Pozzan, A.,;, Zarantonello, P.,;, Seneci, P., J Comb Chem 2001, 3, 224.
15. Patrico, I. V.,;, Raquel, M.,;, Ivorra, M. D.,;, Docon, M. P.,;, Casseles, B. K., J Nat Prod 2003, 66, 954.
16. (a), Randall, O.,;, Kappel, B.,;, Garattini, S.,;, Mussini, E.,;, Randall, L.O., Eds. Benzodiazepines; Raven Press: NewYork, 1973, p 27
17. (b), Schutz, H.,; Benzodiazepines; Springer: Heidelberg, 1982
18. (c), Landquist, J. K., In Comprehensive Heterocyclic Chemistry, 11;, Katritzky, A. R.,;, Rees, C. W., Eds.; Pergamon: Oxford, 1984; 166.
19. (a), Harris, R. C.,;, Straley, J. M., US Patent 1,537, 757, 1968, Chem. Abstr. 73(1970) 100, 054 W)
20. (b), Essaber, M.,;, Baouid, A.,;, Hasnaoui, A.,;, Benharref, A.,;, Lavergne, J. P., Synth Commun 1998, 28, 4097
21. (c), Reddy, K. V. V.,;, Rao, P. S.,;, Ashok, D., Synth Commun 2000, 30, 1825.
22. Aversa, M. C.,;, Ferlazzo, A.,;, Gionnetto, P.,;, Kohnke, F. H., Synthesis 1986, 230.
23. (a), Pan, X. Q.,;, Zou, J. P.,;, Huang, Z. H.,;, Zhang, W., Tetrahedron Lett 2008, 49, 5302
24. (b), Bu, X.,;, Li, Y., Synthesis 1997, 1246.
25. Khatik, G. L.,;, Sharma, G.,;, Kumar, R.,;, Chakraborti, A. K., Tetrahedron 2007, 63, 1200.
26. Surya, K. D.,;, Richard A. G., Tetrahedron Lett 2005, 46, 1811.
27. Sharma, G.,;, Kumar, R.,;, Chakraborti, A., Tetrahedron Lett 2008, 49, 4269.
28. Ganai, B. A.,;, Kumar, S.,;, Andotra, C. S.,;, Kapoor, K. K., Synth Commun 2005, 36, 803.
29. (a), Du, Y.,;, Tian, F.,;, Zhao, W., Synth Commun 2006, 36, 1661
30. (b), Du, Y.,;, Tian, F., J Chem Res 2006, 8, 486
31. (c), Kumar, A.,;, Ahmad, I.,;, Rao, S., J Sulfur Chem 2009, 30, 570.
32. Pant, S.,;, Singhal, B.,;, Upreti, M.,;, Pant, U. C., Molcules 1998, 3, 159.
33. Prakash, O.,;, Kumar, A.,;, Sadana, A.,;, Prakash, R.,;, Singh, S. P.,;, Claramunt, R. M.,;, Sanz, D.,;, Alkorta, I.,;, Elguero, J., Tetrahedron 2005, 61, 6642.
34. (a), Hekmatshoar, R.,;, Sadjadi, S.,;, Shiri, S.,;, Heravi, M. M.,;, Beheshtiha, Y. S., Synth Commun 2009, 39, 2549
35. (b), Shiva kumar, B.,;, Kalyane1, V. N.,;, Shivaram Krishna1, B.,;, Shireesha, B.,;, Reddy, V. M., Int J Pharm Sci Nanotechnol 2010, 2, 756.
36. Kodomari, M.,;, Noguchi, T.,;, Aoyama, T., Synth Commun 2004, 34, 1783.
37. Sharma, G.,;, Kumar, R.,;, Chacraborti, A. K., Tetrahedron Lett 2008, 49, 4272.
38. Orlov, V. D.,;, Kolos, N. N.,;, Ruzhitskaya, N. N., Chem Heterocycl Comp 1983, 19, 1293.
39. (a), Rogers, R. D.,;, Sedden, K. R., Science 2003, 302, 792
40. (b), Sheldon, R., Green Chem 2005, 7, 267
41. (c), Hanke, C. G.,;, Afamas, N. A.,;, Lynden-Bell, R. M., Green Chem 2002, 4, 107
42. (d), Wang, Y.,;, Li, H.,;, Han, S., J Chem Phys 2005, 123, 174501
43. (e), Wang, Y.,;, Li, H.,;, Han, S., J Chem Phys 2006, 124, 044504.
44. Li, R.,;, Kenyon, G. L.,;, Cohen, F. E.,;, Chen, X.,;, Gong, B.,;, Dominguez, J. N.,;, Davidson, E.,;, Kurzban, G.,;, Millar, R. E.,;, Nuzum, E. O.,;, Rosenthal, P. J.,;, Mckerrow, J. H., J Med Chem 1995, 38, 5031.
45. Bradaric, C. J.,;, Downard, A.,;, Kennedy, C.,;, Robertson, A. J.,;, Zhou, Y., Green Chem 2003, 5, 143.
46. Jarikote, D. V.,;, Siddiqui, S. A.,;, Rajagopal, R.,;, Daniel, T.,;, Lahoti, R. J.,;, Srinivasan, K. V., Tetrahedron Lett 2003, 44, 1835.
47. (a), Braun, U. R.,;, Muller, T. J. J., Tetrahedron 2004, 60, 9463
48. (b), Escobar, C. A.,;, Orellana-Vera, J.,;, Vega, A.,;, Sicker, D.,;, Sieler, J. Z., Naturforsch 2009, 64b, 969
49. (c), Escobar, C. A.,;, Donoso-Tauda, O.,;, Araya-Maturana, R.,;, Vega, A., Cryst Struct Commun 2007, C63, 426.
50. (a), Parvez, M.,;, Umbreen, S.,;, Ansari, F. L., Acta Crystallogr Cryst Struct Commun 2003, C59, 298
51. (b), Ansari, F. L.,;, Wadood, A.,;, Ullah, A.,;, Iftikhar, F.,;, Ul-Haq, Z., J Enzym Inhib Med Chem 2009, 24, 151.
52. Liu, M.,;, Wilairat, P.,;, Croft, S. L.,;, Tan, A. L.,;, Go, M., Bioorg Med Chem 2003, 11, 2729.
53. Hoshino, Y.,;, Takeno, N., Bull Chem Soc Jpn 1986, 59, 2903.
54. Ryoka, M.,;, Hiroyuki, K., J Chem Soc Perkin Trans II 1985, 743.
55. Cabrera, M.,;, Simoens, M.,;, Falchi, G.,;, Lavaggi, M. L.,;, Piro, O. E.,;, Castellano, E. E.,;, Vidal, A.,;, Azqueta, A.,;, Monge, A.,;, Cerine, A. L.,;, Sagrera, G., Bioorg Med Chem 2007, 15, 3356.
56. Powers, D. G.,;, Casebier, D. S.,;, Fokas, D.,;, Ryan, W. J.,;, Troth, J. R.,;, Coffen, D. L., Tetrahedron 1998, 54, 4085.
57. Suman, M.,;, Singh, R.,;, Malik, M. S.,;, Kathpal, T. S.,;, Malik, O. P., Indian J Chem 1995, 34B, 743.
58. Montes-Avila, J.,;, Diaz-Camacho, S. P.,;, Sicairos-Felix, J.,;, Delgado-Vargas, F.,;, Rivero, I. A., Bioorg Med Chem 2009, 17, 6780.
59. Khatik, G. L.,;, Kumar, R.,;, Chakraborti, A. K., Synthesis 2007, 541.
60. Parvez, M.,;, Umbreen, S.,;, Ansari, F. L., Cryst Struct Commun 2003, C59 (6), 0298.
61. Ansari, F. L.,;, Latif, H.,;, Nasir, S., Rapid Commun Mass Spectrom 2005, 19, 1200.
62. Xu, J.,;, Jin, S.,;, Xing, Q., Phosphorus, Sulfur & Silicon and the related Elements 1998, 141, 57.
63. Higashi, T., Shape program for absorption; Rigaku Corporation: Tokyo, 2005.
64. Burla, M. C.,;, Caliandro, R.,;, Camalli, M.,;, Carrozzini, B.,;, Cascarano, G. L.,;, De Caro, L.,;, Giacovazzo, C.,;, Polidori, G.,;, Spagna, R., J Appl Cryst 2005, 38, 381.
65. Sheldrich, G. M., SHELXL97; University of Gottingen: Germany, 1997.