DOI QR코드

DOI QR Code

Alum Catalyzed Convenient Synthesis of Quino[2,3-b][1,5 benzoxazepine α-Aminophosphonate Derivatives

  • Sonar, Swapnil S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Sadaphal, Sandip A. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Shitole, Nana V. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Jogdand, Nivrutti R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Shingate, Bapurao B. (National Chemical Laboratory) ;
  • Shingare, Murlidhar S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
  • Published : 2009.08.20

Abstract

We have described an efficient synthesis of quino[2,3-b][1,5]benzoxazepine α-aminophosphonate derivatives by the nucleophilic addition of triethyl phosphite to substituted quino[2,3-b][1,5]benzoxazepines promoted by easily available, inexpensive and mild catalyst KAl(S$O_4)_2{\cdot}12H_2$O(alum). The reactions proceed smoothly at room temperature under solvent-free reaction conditions and providing high yield of product in very short reaction time.

Keywords

References

  1. Quin, L. D.; Quin, G. S. A Guide to Organophosphorus Chemistry; John Wiley & Sons Ltd: New York, 2000; p 351
  2. Corbridge, D. E. C. Phosphorus Chemistry, Biochemistry & Technology; Elsevier: Amsterdam, 2000; p 835. https://doi.org/10.1039/p19840002845
  3. Baylis, E. K.; Campbell, C. D.; Dingwall, J. G. J. Chem. Soc. Perkin Trans 1 1984, 2845 https://doi.org/10.1039/p19840002845
  4. Allen, M. C.; Fuhrer, W.; Truck, B.; Wade, R.; Wood, J. M. J. Med. Chem. 1989, 32, 1652 https://doi.org/10.1021/np960250m
  5. Kafraski, P.; Lejezak, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 63, 193 https://doi.org/10.1021/jm00294a022
  6. Hirschmann, R.; Smith, A. B.; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengler, P. A.; Venkovic, S. J. Science 1994, 265, 234. https://doi.org/10.1126/science.8023141
  7. Pokalwar, R. U.; Hangarge, R. V.; Maske, P. V.; Shingare, M. S. Arkivoc 2006, xi, 196
  8. Mccormick, J. L.; Mckee, T. C.; Cardellina, J. H.; Boyd, M. R. J. Nat. Prod. 1996, 59, 469 https://doi.org/10.1021/np960250m
  9. Nadaraj, V.; Selvi, S. T.; Sasi, R. Arkivoc 2006, x, 82. https://doi.org/10.1021/ol990079g
  10. Craig, J. C.; Person, P. E. J. Med. Chem. 1971, 14, 1221 https://doi.org/10.1021/jm00294a022
  11. Dillard, R. D.; Pavey, D. E.; Benslay, D. N. J. Med. Chem. 1973, 16, 251 https://doi.org/10.1021/cr940089p
  12. Sukhova, N. M.; Lidak, M.; Zidermane, A.; Pelevina, I. S.; Voronia, S. S. Khim. Farm. Zh. 1989, 23, 1226
  13. Atwell, G. J.; Bangaley, B. C.; Denny, W. A. J. Med. Chem. 1989, 32, 396 https://doi.org/10.1021/jm00122a018
  14. Patel, H. V.; Vyas, K. V.; Fernandes, P. S. Indian J. Chem. 1990, 29(B), 836 https://doi.org/10.1039/b106871g
  15. Saito, I.; Sando, S.; Nakatani, K. Bio. Org. Med. Chem. 2001, 9, 2381. https://doi.org/10.1016/S0968-0896(01)00160-2
  16. Jilek, J. O.; Pomykacek, J.; Metysova, J.; Metys, J.; Protiva, M. Collect. Czech. Chem. Commun. 1965, 30, 363
  17. Coyne, W. E.; Cusic, J. W. J. Med. Chem. 1967, 10, 541 https://doi.org/10.1021/jm00316a009
  18. Coyne, W. E.; Cusic, J. W. J. Med. Chem. 1968, 11, 1158 https://doi.org/10.1021/jm00312a012
  19. Sanner, J. H.; Muller, R. A. Pharmacologist 1974, 16, 324
  20. Allen, R. C.; Reitano, P. A.; Urbach, H. J. Med. Chem. 1978, 21, 838 https://doi.org/10.1021/jm00206a027
  21. Nagarajan, K.; David, J.; Kulkarni, Y. S.; Hendi, S. B.; Shenoy, S. J.; Upadhyaya, P. Eur. J. Med. Chem. 1986, 21, 21.
  22. Basavaraju, B.; Naik, H. S. B.; Prabhakara, M. C. Bioinorg. Chem. Applications 2007, 1, doi:10.1155/2007/42587
  23. Petov, K. A.; Chauzov, V. A.; Erkhina, T. S. Usp. Khim. 1974, 43, 2045
  24. Zou, J. Pol. J. Chem. 1981, 55, 643
  25. Laschat, S.; Kunz, H. Synthesis 1992, 90
  26. Kabanchnik, M. M.; Ternovskaya, T. N.; Zobnina, E. V.; Beletskaya, I. P. Russian J. Org. Chem. 2002, 38, 480 https://doi.org/10.1023/A:1016578602100
  27. Kabanchnik, M. M.; Zobnina, E. V.; Beletskaya, I. P. Russian J. Org. Chem. 2005, 41, 505. https://doi.org/10.1007/s11178-005-0194-y
  28. Ranu, B. C.; Hajra, A.; Jana, U. Org. Lett. 1999, 1, 1141 https://doi.org/10.1021/ol990079g
  29. Yadav, J. S.; Reddy, B. V. S.; Raj, S.; Reddy, K. B.; Prasad, A. R. Synthesis 2001, 2277
  30. Sun, P. P.; Hu, Z. X.; Huang, Z. H. Synth. Commun. 2004, 34, 4293 https://doi.org/10.1081/SCC-200039361
  31. Zhan, Z. P.; Li, J. P. Synth. Commun. 2005, 35, 2501 https://doi.org/10.1080/00397910500212692
  32. Kumar, A. S.; Taneja, S. C.; Hundal, M. S.; Kapoor, K. K. Tetrahedron Lett. 2008, 49, 2208. https://doi.org/10.1016/j.tetlet.2008.02.047
  33. Chandrashekar, S.; Narsihmulu, C.; Sultana, S.; Saritha, B.; Prakash, S. Synlett 2003, 505
  34. Akiyama, T.; Sanada, M.; Fuchibe, K. Synlett 2003, 1463
  35. Azizi, N.; Rajabi, F.; Saidi, M. R. Tetrahedron Lett. 2004, 45, 9233 https://doi.org/10.1016/j.tetlet.2004.10.092
  36. Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Synthesis 2004, 2692
  37. Elmakssoudi, A.; Zahouily, M.; Mezdar, A.; Rayadh, A.; Sebti, S. Comptes Rendus Chim. 2005, 8, 1954 https://doi.org/10.1016/j.crci.2005.05.006
  38. Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2008, 73, 6029 https://doi.org/10.1021/jo8009006
  39. Kaboudin, B.; Jafari, E. Synlett 2008, 1837.
  40. Tanaka, K. F. Chem. Rev. 2000, 100, 1025 https://doi.org/10.1021/cr940089p
  41. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. J. Org. Chem. 2005, 70, 350 https://doi.org/10.1021/jo049138g
  42. Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgary, G.; Mohammadi, A. A. Tetrahedron Lett. 2005, 46, 6123 https://doi.org/10.1016/j.tetlet.2005.06.157
  43. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. Applied Catalysis 2006, 300, 85 https://doi.org/10.1016/j.apcata.2005.11.001
  44. Dabiri, M.; Baghbanzadeh, M.; Kiani, S.; Vakilzadeh, Y. Monatshefte Fur Chieme 2007, 138, 997 https://doi.org/10.1007/s00706-007-0666-6
  45. Mohammadi, A. A.; Mivechi, M.; Kefayati, H. Monatshefte Fur Chieme 2008, 139, 935 https://doi.org/10.1007/s00706-008-0875-7
  46. Pawar, S. S.; Dekhane, D. V.; Shingare, M. S.; Thore, S. N. Aust. J. Chem. 2008, 61, 905. https://doi.org/10.1071/CH08122
  47. Chavan, V. P.; Mane, A. S.; Shingare, M. S. Indian J. Chem. 2001, 40B, 339
  48. Mane, A. S.; Chavan, V. P.; Karale, B. K.; Hangarge, R. V.; Gaikwad, M. S.; Shingare, M. S. Synthetic Commun. 2002, 32, 2633 https://doi.org/10.1081/SCC-120006025
  49. Pokalwar, R. U.; Hangarge, R. V.; Madje, B. R.; Ware, M. N.; Shingare, M. S. Phosphorus, Sulfur, Silicon, Relat. Elem. 2008, 183, 1470
  50. Sonar, S. S.; Kategaonkar, A. H.; Gill, C. H.; Shingate, B. B.; Shingare, M. S. Arkivoc 2009, ii, 138.
  51. Hangarge, R. V.; Sonwane, S. A.; Jarikote, D. V.; Shingare, M. S. Green Chem. 2001, 3, 310 https://doi.org/10.1039/b106871g
  52. Hangarge, R. V.; Jarikote, D. V.; Shingare, M. S. Green Chem. 2002, 4, 266 https://doi.org/10.1039/b111634g
  53. Madje, B. R.; Patil, P. T.; Shindalkar, S. S.; Benjamin, S. B.; Shingare, M. S.; Dongare, M. K. Catalysis Commun. 2004, 5, 353 https://doi.org/10.1016/j.catcom.2004.04.004
  54. Pawar, S. S.; Dekhane, D. V.; Shingare, M. S.; Thore, S. N. Tetrahedron Lett. 2008, 49, 4252 https://doi.org/10.1016/j.tetlet.2008.04.148
  55. Pawar, S. S.; Uppalla, L. S.; Shingare, M. S.; Thore, S. N. Tetrahedron Lett. 2008, 49, 5 https://doi.org/10.1016/j.tetlet.2008.07.101
  56. Pawar, S. S.; Dekhane, D. V.; Shingare, M. S.; Thore, S. N. Chin. Chemical Lett. 2008, 19, 1055 https://doi.org/10.1016/j.cclet.2008.06.028
  57. Sadaphal, S. A.; Shelke, K. F.; Sonar, S. S.; Shingare, M. S. Central Euro. J. Chem. 2008, 6, 662.

Cited by

  1. )-one Derivatives pp.0022152X, 2013, https://doi.org/10.1002/jhet.1075
  2. One-pot tandem Ugi-4CR/ $$\hbox {S}_{N}$$ S N Ar approach to highly functionalized quino[2,3-b][1,5]benzoxazepines vol.20, pp.2, 2016, https://doi.org/10.1007/s11030-015-9651-x
  3. [Et3NH][HSO4]-catalyzed one-pot, solvent-free synthesis and biological evaluation of α-amino phosphonates vol.42, pp.5, 2016, https://doi.org/10.1007/s11164-015-2348-z
  4. ]quinolin- 4-ylmethanol derivatives pp.10981071, 2009, https://doi.org/10.1002/hc.20570
  5. ChemInform Abstract: Alum Catalyzed Convenient Synthesis of Quino[2,3-b][1,5]benzoxazepine α-Aminophosphonate Derivatives. vol.41, pp.1, 2010, https://doi.org/10.1002/chin.201001184