Ceric ammonium nitrate-catalyzed azidation of 1,2-anhydro sugars: Application in the synthesis of structurally diverse sugar-derived morpholine 1,2,3-triazoles and 1,4-oxazin-2-ones

Journal of Organic Chemistry

Volumn 76, Issue 15, 2011, Pages 5972-5984

  Reddy, Y Suman ^a   John Pal, A P ^a   Gupta, Preeti ^a   Ansari, Alafia A ^a   Vankar, Yashwant D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,2 ,3-TRIAZOLES; AZIDATION; CATALYTIC AMOUNTS; CERIC AMMONIUM NITRATE; GLYCOSIDASES; GOOD YIELD; MICROMOLAR RANGE; MORPHOLINES; STEREOSELECTIVE MANNER; SUGAR DERIVATIVES;

AMMONIUM COMPOUNDS;

SUGARS;

1,4 OXAZIN 2 ONE; AMMONIUM NITRATE; CERIUM; GLYCOSIDASE; MORPHOLINE 1,2,3 TRIAZOLE; MORPHOLINE DERIVATIVE; OXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AZIDATION; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; MOLECULAR INTERACTION; PHYSICAL CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

CARBOHYDRATES; CATALYSIS; CERIUM; MOLECULAR STRUCTURE; MORPHOLINES; OXAZINES; TRIAZOLES;

EID: 79961070844     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200260w     Document Type: Article

References (81)

1. Wang, X. L.; Wan, K.; Zhou, C. H. Eur. J. Med. Chem. 2010, 45, 4631
2. Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. E.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953
3. Da Silva, F. C.; De Souza, M. C. B V.; Frugulhetti, I. I. P.; Castro, H. C.; Souza, S. L. O.; de Souza, T. M. L.; Rodrigues, D. Q.; Souza, A. M. T.; Abreu, P. A.; Passamani, F.; Rodrigues, C. R.; Ferreira, V. F. Eur. J. Med. Chem. 2009, 44, 373
4. Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; De Clercq, E.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185
5. Wamhoff, H. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, p 669.
6. Kallander, L. S.; Lu, Q.; Chen, W.; Tomaszek, T.; Yang, G.; Tew, D.; Meek, T. D.; Hofmann, G. A.; Schulz-Pritchard, C. K.; Smith, W. W.; Janson, C. A.; Ryan, M. D.; Zhang, G. F.; Johanson, K. O.; Kirkpatrick, R. B.; Ho, T. F.; Fisher, P. W.; Mattern, M. R.; Johnson, R. K.; Hansbury, M. J.; Winkler, J. D.; Ward, K. W.; Veber, D. F.; Thompson, S. K. J. Med. Chem. 2005, 48, 5644
7. Costa, M. S.; Boechat, N.; Rangel, E. A.; Da Silva, F. C.; De Souza, A. M. T.; Rodrigues, C. R.; Castro, H. C.; Junior, I. N.; Lourenço, M. C. S.; Wardell, S. M. S. V.; Ferreira, V. F. Bioorg. Med. Chem. 2006, 14, 8644
8. Bock, V. D.; Speijer, D.; Hiemstra, H.; van Maarseveen, J. H. Org. Biomol. Chem. 2007, 5, 971
9. Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. J. Med. Chem. 1986, 29, 2262
10. Heightman, T. D.; Vasella, A.; Tsitsanou, K. E.; Zographos, S. E.; Skamnaki, V. T.; Oikonomakos, N. G. Helv. Chim. Acta 1998, 81, 853
11. Krulle, T. M.; Fuente, C. D.; Pickering, L; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. Tetrahedron: Asymmetry 1997, 8, 3807
12. Heightman, T. D.; Locatelli, M.; Vasella, A. Helv. Chim. Acta 1996, 79, 2190
13. Ramachary, D. B.; Reddy, G. B.; Mondal, R. Tetrahedron Lett. 2007, 48, 7618
14. Chuprakov, S.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V. Org. Lett. 2007, 9, 2333
15. Gil, M. V.; Arevalo, M. J.; Lopez, O. Synthesis 2007, 1589
16. Krivopalov, V. P.; Shkurko, O. P. Russ. Chem. Rev. 2005, 74, 339.
17. Godovikova, T. I.; Ignateva, E. L.; Khmelnitskii, L. I. Chem. Heterocycl. Compd. 1989, 25, 113
18. Wu, Y. M.; Deng, J.; Chen, Q. Y. Synlett 2006, 645
19. Sudhir, V. S.; Kumar, N. Y. P.; Baig, R. B. N.; Chandrasekaran, S. J. Org. Chem. 2009, 74, 7588
20. Yanai, H.; Obara, S.; Taguchi, T. Org. Biomol. Chem. 2008, 6, 2679
21. Anegundi, R. I.; Puranik, V. G.; Hotha, S. Org. Biomol. Chem. 2008, 6, 779 and references therein.
22. For a review see: Wijtmans, R.; Vink, M. K. S.; Schoemaker, H. E.; van Delft, F. L.; Blaauw, R. H.; Rutjes, F. P. J. T. Synthesis 2004, 641 For recent examples, see: Breuning, M.; Winnacker, M.; Steiner, M. Eur. J. Org. Chem. 2007, 2100
23. Dghooghe, M.; Vanlangendonck, T.; Thrnroos, K. W.; De Kimpe, N. J. Org. Chem. 2006, 71, 4678
24. Pedrosa, R.; Andris, C.; Mendiguchja, P.; Nieto, J. J. Org. Chem. 2006, 71, 8854
25. Wilkinson, M. C. Tetrahedron Lett. 2005, 46, 4773
26. Lanman, B. A.; Myers, A. G. Org. Lett. 2004, 6, 1045
27. Audouze, K.; Nielsen, E, O.; Peters, D. J. Med. Chem. 2004, 47, 3089
28. Abramova, T. V.; Bakharev, P. A.; Svetlana, V.; Silinikov, V. N. Tetrahedron Lett. 2004, 45, 4361
29. Hajos, M.; Fleishaker, J. C.; Filipiak-Reisner, J. K.; Brown, M. T.; Wong, E. H.F. CNS Drug Rev. 2004, 10, 23 and references therein
30. Kesiciki, E. A.; Kaufman, R. J.; Halbrook, J.; Kashishian, A.; Fowler, K. W. Abstr. Pap. Am. Chem. Soc. 2003, 226, U13
31. Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2008, 47, 3784
32. Albanese, D.; Salsa, M.; Landini, D.; Lupi, V.; Penso, M. Eur. J. Org. Chem. 2007, 2107
33. Henegar, K. E. J. Org. Chem. 2008, 73, 3662
34. Khodair, A. I.; Pachamuthu, K.; Schmidt, R. R. Synthesis 2004, 53
35. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
36. Chowdhury, C.; Mukherjee, S.; Das, B.; Achari, B. J. Org. Chem. 2009, 74, 3612
37. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952
38. Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171
39. Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998
40. Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897
41. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853
42. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057
43. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
44. Bianchi, A.; Bernardi, A. J. Org. Chem. 2006, 71, 4565 and references therein
45. De Cienfuegos, L. A.; Rodríguez, C.; Mota, A. J.; Robles, R. Org. Lett. 2003, 5, 2743
46. Coe, D. M.; Myers, P. L.; Parry, D. M.; Roberts, S. M.; Storer, R. J. Chem. Soc., Chem. Commun. 1990, 151
47. The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: New York, 1971.
48. Jacobs, G. A.; Tino, J. A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955
49. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297
50. Reddy, B. G.; Madhusudanan, K. P.; Vankar, Y. D. J. Org. Chem. 2004, 69, 2630
51. Murphy, P. V.; Bradley, H.; Tosin, M.; Pitt, N.; Fitzpatrick, G. M.; Glass, W. K. J. Org. Chem. 2003, 68, 5692
52. Rawal, G. K.; Rani, S.; Madhusudanan, K. P.; Vankar, Y. D. Synthesis 2007, 294
53. Gupta, P.; Vankar, Y. D. Eur. J. Org. Chem. 2009, 1925
54. Kumari, N.; Reddy, B. G.; Vankar, Y. D. Eur. J. Org. Chem. 2008, 160
55. O'brein, J. L.; Tosin, M.; Murphy, P. V. Org. Lett. 2001, 3, 3353
56. Cronin, L.; Murphy, P. V. Org. Lett. 2005, 7, 2691
57. Kumari, N.; Vankar, Y. D. Org. Biomol. Chem. 2009, 7, 2104
58. Gyorgydeak, Z.; Szila gyi, L.; Pausen, H. J. Carbohydr. Chem. 1993, 12, 139
59. Gyorgydeak, Z.; Thiem, J. Carbohydr. Res. 1995, 268, 85
60. Kawabata, H.; Kubo, S.; Hayashi, M. Carbohydr. Res. 2001, 333, 153
61. Yadav, J. S.; Reddy, B. V. S.; Chand, P. K. Tetrahedron Lett. 2001, 42, 4057
62. Yadav, J. S.; Reddy, B. V. S. Synthesis 2002, 511
63. Lee, G. S.; Min, H. K.; Chung, B. Y. Tetrahedron Lett. 1999, 40, 543
64. Nair, V.; Deepthi, A. Chem. Rev. 2007, 107, 1862
65. Iranpoor, N.; Kazemi, F. Synth. Commun. 1999, 29, 561
66. Rawal, G. K.; Kumar, A.; Tawar, U.; Vankar, Y. D. Org. Lett. 2007, 9, 5171
67. Rawal, G. K.; Rani, S.; Kumari, N.; Vankar, Y. D. J. Org. Chem. 2009, 74, 5349
68. Kancharla, P. K.; Vankar, Y. D. J. Org. Chem. 2010, 75, 8457
69. Jayakanthan, K.; Vankar, Y. D. Tetrahedron Lett. 2006, 47, 8667
70. Jayakanthan, K.; Vankar, Y. D. Org. Lett. 2005, 7, 5441
71. Reddy, B. G.; Vankar, Y. D. Angew. Chem., Int. Ed. 2005, 44, 2001 and references cited therein
72. John Pal, A. P.; Vankar, Y. D. Tetrahedron Lett. 2010, 51, 2519
73. John Pal, A. P.; Gupta, P.; Reddy, Y. S.; Vankar, Y. D. Eur. J. Org. Chem. 2010, 6957
74. Cheshev, P.; Marra, A.; Dondoni, A. Carbohydr. Res. 2006, 341, 2714
75. Honda, E.; Gin, D. Y. J. Am. Chem. Soc. 2002, 124, 7343
76. Furstner, A.; Radkowski, K.; Grabowski, J.; Wirtz, C.; Mynott, R. J. Org. Chem. 2000, 65, 8758
77. Randolph, J. T.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 8473
78. Gordon, D. M.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 3713
79. Du, Y.; Fanzuo, K. Tetrahedron Lett. 1995, 36, 427
80. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. 1996, 35, 1380
81. Li, Y. T.; Li, S. C. In Methods in Enzymology; Ginsberg, V., Ed.; Academic: New York, 1972; p 702.