An efficient synthesis and antibacterial screening of novel oxazepine α-aminophosphonates by ultrasound approach

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 185, Issue 1, 2009, Pages 65-73

  Sonar, Swapnil S ^a   Sadaphal, Sandip A ^a   Labade, Vilas B ^a   Shingate, Bapurao B ^a   Shingare, Murlidhar S ^a  

^a DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

P TSA; Quino 2,3 b 1,5 benzoxazepine; Solvent free; Triethyl phosphite; Ultrasound irradiation; Aminophosphonates

Indexed keywords

EID: 74949133328     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500802713259     Document Type: Article

References (64)

1. (a) L. D. Quin and G. S. Quin, A Guide to Organophosphorus Chemistry (John Wiley & Sons Ltd., New York, 2000), p. 351;
2. (b) D. E. C. Corbridge, Phosphorus Chemistry, Biochemistry & Technology (Elsevier, Amsterdam, 2000), p. 835.
3. (a) E. K. Baylis, C. D. Campbell, and J. G. Dingwall, J. Chem. Soc., Perkin Trans 1, 2845 (1984);
4. (b) M. C. Allen, W. Fuhrer, B. Truck, R. Wade, and J. M. Wood, J. Med. Chem., 32, 1652 (1989);
5. (c) P. Kafraski and B. Lejezak, Phosphorus, Sulfur, and Silicon, 63, 193 (1991);
6. (d) R. Hirschmann, A. B. Smith, C. M. Taylor, P. A. Benkovic, S. D. Taylor, K. M. Yager, P. A. Sprengler, and S. J. Venkovic, Science, 265, 234 (1994).
7. R. U. Pokalwar, R. V. Hangarge, P. V. Maske, and M. S. Shingare, Arkivoc, xi,196 (2006).
8. (a) J. L. McCormick, T. C. Mckee, J. H. Cardellina, and M. R. Boyd, J. Nat. Prod., 59, 469 (1996);
9. (b) I. S. Chen, H. F. Chen, M. J. Cheng, Y. L. Chang, C. M. Teng, I. Tsutomu, J. J. Chen, andI.L.Tsai, J. Nat. Prod., 64, 1143 (2001);
10. (c) V. Nadaraj, S. T. Selvi, and R. Sasi, Arkivoc, x,82 (2006).
11. (a)J.C.Craig andP.E.Person, J. Med. Chem., 14, 1221 (1971);
12. (b) R. D. Dillard, D. E. Pavey, and D. N. Benslay, J. Med. Chem., 16, 251 (1973);
13. (c) N. M. Sukhova, M. Lidak, A. Zidermane, I. S. Pelevina, and S. S. Voronia, Khim. Farm. Zh., 23, 1226 (1989);
14. (d) G. J. Atwell, B. C. Bangaley, and W. A. Denny, J. Med. Chem., 32, 396 (1989);
15. (e) H. V. Patel, K. V. Vyas, and P. S. Fernandes, Indian J. Chem., 29(B), 836 (1990);
16. (f) I. Saito, S. Sando, and K. Nakatani, Bioorg. Med. Chem., 9, 2381 (2001).
17. (a) J. O. Jilek, J. Pomykacek, J. Metysova, J. Metys, and M. Protiva, Collect. Czech. Chem. Commun., 30, 363 (1965);
18. (b) W. E. Coyne and J. W. Cusic, J. Med. Chem., 10,541 (1967);
19. (c) W. E. Coyne and J. W. Cusic, J. Med. Chem., 11,1158 (1968);
20. (d) J. H. Sanner and R. A. Muller, Pharmacologist, 16,324 (1974);
21. (e) R. C. Allen, P. A. Reitano, and H. Urbach, J. Med. Chem., 21,838 (1978);
22. (f) K. Nagarajan, J. David, Y. S. Kulkarni, S. B. Hendi, S. J. Shenoy, and P. Upadhyaya, Eur. J. Med. Chem., 21,21 (1986).
23. B. Basavaraju, H. S. B. Naik, and M. C. Prabhakara, Bioinorg. Chem. Appl., 1 (2007), doi:10.1155/2007/42587.
24. (a) G. P. Zecchini, I. Torrini, and M. P. Paradisi, Heterocycles, 26, 2443 (1987);
25. (b) R. N. Kumar, T. Suresh, and P. S. Mohan, J. Ind. Chem. Soc., 79, 774 (2002).
26. (a) K. A. Petov, V. A. Chauzov, and T. S. Erkhina, Usp. Khim., 43,2045 (1974);
27. (b) J. Zou, Pol. J. Chem., 55,643 (1981);
28. (c) S. Laschat and H. Kunz, Synthesis, 90 (1992);
29. (d) M. M. Kabanchnik, T. N. Ternovskaya, E. V. Zobnina, and I. P. Beletskaya, Russ. J. Org. Chem., 38, 480 (2002);
30. (e) M. M. Kabanchnik, E. V. Zobnina, and I. P. Beletskaya, Russ. J. Org. Chem., 41,505 (2005).
31. (a) B. C. Ranu, A. Hajra, and U. Jana, Org. Lett., 1,1141 (1999);
32. (b) J. S. Yadav, B. V. S. Reddy, S. Raj, K. B. Reddy, and A. R. Prasad, Synthesis, 2277 (2001);
33. (c) P. P. Sun, Z. X. Hu, and Z. H. Huang, Synth. Commun., 34,4293 (2004);
34. (d) Z. P. Zhan and J. P. Li, Synth. Commun., 35,2501 (2005);
35. (e) A. S. Kumar, S. C. Taneja, M. S. Hundal, and K. K. Kapoor, Tetrahedron Lett., 49,2208 (2008).
36. (a) T. Akiyama, M. Sanada, and K. Fuchibe, Synlett, 1463 (2003);
37. (b) N. Azizi, F. Rajabi, and M. R. Saidi, Tetrahedron Lett., 45,9233 (2004);
38. (c) H. Firouzabadi, N. Iranpoor, and S. Sobhani, Synthesis, 2692 (2004);
39. (d) A. Elmakssoudi, M. Zahouily, A. Mezdar, A. Rayadh, and S. Sebti, Comptes Rendus Chim. , 8,1954 (2005).
40. M. Xia and Y. Lu, Ultrasound SonoChem., 14,235 (2007).
41. K. F. Tanaka, Chem. Rev., 100,1025 (2000).
42. (a) T.J. Mason and J.P. Lorimer, In Sonochemistry: Theory, Application and Uses of Ultrasound in Chemistry, E. Horwood, ed. (John Wiley, New York, 1988);
43. (b) K. S. Suslick, Ed., Ultrasound, Its Chemical, Physical and Biological Effects (VCH, Weinheim, Germany, 1988);
44. (c) A. Gaplovsky, M. Gaplovsky, S. Toma, and J. L. Luche, J. Org. Chem., 65,8444 (2000);
45. (d) R. R. Deshmukh, R. Rajagopal, and K. V. Srinivasan, Chem. Commun., 1544 (2001);
46. (e) R. Rajagopal, D. V. Jarikote,K.V.Srinivasan, Chem. Commun., 616 (2002);
47. (f) G. Cravotto and P. Cintas, Chem. Soc. Rev., 35,180 (2006);
48. (g) A Shaabani, A. H. Rezayan, A. Rahmati, and M. Sharifi, Monatsh. Chem., 137,77 (2006);
49. (h) C. M. P. Pereira, H. A. Stefani, K. P. Guzen, and A. T. G. Orfao, Lett. Org. Chem., 4,43 (2007);
50. (i) J. T. Li, X. H. Zhang, and Z. P. Lin, Bailest.J.Org. Chem., 3,13 (2007).
51. (a) H. R. Brinkman, J. J. Landi Jr., J. B. Paterson Jr., and P. J. Stone, Synth. Commun., 21,459 (1991);
52. (b) R. Y. Yang and L. X. Dai, Synth. Commun., 24, 2229 (1994);
53. (c) M. Narasimhulua, K. C. Mahesha, T. S. Reddya, K. Rajesha, and Y. Venkateswarlu, Tetrahedron Lett., 47, 4381 (2006);
54. (d) L. Tao, S. Yoshie, and X. Qiang, Catalysis Today, 111,288 (2006).
55. (a) V. P. Chavan, A. S. Mane, and M. S. Shingare, Indian J. Chem., 40B, 339 (2001);
56. (b) A. S. Mane, V. P. Chavan, B. K. Karale, R. V. Hangarge, M. S. Gaikwad, and M. S. Shingare, Synth. Commun., 32, 2633 (2002);
57. (c) R. U. Pokalwar, R. V. Hangarge, B. R. Madje, M. N. Ware, and M. S. Shingare, Phosphorus, Sulfur, and Silicon, 183, 1470 (2008).
58. (a) R. V. Hangarge, S. A. Sonwane, D. V. Jarikote, and M. S. Shingare, Green Chem., 3,310 (2001);
59. (b) R. V. Hangarge, D. V. Jarikote, and M. S. Shingare, Green Chem., 4, 266 (2002);
60. (c) B. R. Madje, P. T. Patil, S. S. Shindalkar, S. B. Benjamin, M. S. Shingare, and M. K. Dongare, Catalysis Commun., 5,353 (2004);
61. (d) S. S. Pawar, D. V. Dekhane, M. S. Shingare, and S. N. Thore, Tetrahedron Lett., 49,4252 (2008);
62. (e) S. S. Pawar, L. S. Uppalla, M. S. Shingare, and S. N. Thore, Tetrahedron Lett., 49,5858 (2008);
63. (f) S. S. Pawar, D. V. Dekhane, M. S. Shingare, andS.N.Thore, Chin. Chem. Lett., 19,1055 (2008).
64. A. Kilic, M. Baysallar, B. Besirbellioglu, B. Salih, K. Sorkun, and M. Tanyuksel, Ann. Microbiol., 55, 113 (2005).