One-pot three-component synthesis of dihydrobenzo- and naphtho[e]-1,3- oxazines in water

Journal of Heterocyclic Chemistry

Volumn 46, Issue 5, 2009, Pages 1003-1006

  Mathew, Bijoy P ^a   Nath, Mahendra ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; NAPHTHOXAZINE DERIVATIVE; OXAZINE DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENVIRONMENTAL TEMPERATURE; MANNICH REACTION; METHODOLOGY; ONE POT SYNTHESIS; POLYMERIZATION;

EID: 70349260841     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.147     Document Type: Article

References (53)

1. (a) Lindstron, U. M. Chem Rev 2002, 102, 2751;
2. (b) Wasserscheid, P.; Welton, T., Eds. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, 2003;
3. (c) Jessop, P. G.; Leitner, W., Eds. Chemical Synthesis Using Supercritical Fluids; Wiley-VCH: Weinheim, 1999;
4. (d) Tanaka, K. Solvent-Free Organic Synthesis; Wiley-VCH: Weinheim, 2003;
5. (e) Sheldon, R. A. Green Chem 2005, 7, 267.
6. (a) Kobayashi, S.; Manabe, K. Acc Chem Res 2002, 35, 209;
7. (b) Li, C.-J. Chem Rev 2005, 105, 3095.
8. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew Chem Int Ed Engl 2005, 44, 3275.
9. Amantini, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Green Chem 2001, 3, 229.
10. Fringuelli, F.; Piermatti, O.; Pizzo, F. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academie and Professional: London, 1998; p 223.
11. Lindstrom, U. M.; Ding, R.; Hidestal, O. Chem Commun 2005, 1773.
12. (a) Matsushita, M.; Kamata, K.; Yamaguchi, K.; Mizuno, N. J Am Chem Soc 2005, 127, 6632;
13. (b) Schlatter, A.; Kundu, M. K.; Woggon, W.-D. Angew Chem Int Ed Engl 2004, 43, 6731.
14. Li, C.-J.; Chen, L. Chem Soc Rev 2006, 35, 68.
15. Ribe, S.; Wipf, P. Chem Commun 2001, 299.
16. (a) Kuehne, M. E.; Konopke, E. A. J Med Chem 1962, 5, 257;
17. (b) Kuehne, M. E.; Konopke, E. A.; Lamberd, B. F. J Med Chem 1962, 5, 281;
18. (c) Chylinska, J. B.; Urbanski, T. J Med Chem 1963, 6, 484;
19. (d) Hsu, L.-Y.; Lin, C.-H. Heterocycles 1996, 43, 2687.
20. Chylinska, J. B.; Janowiec, M.; Urbanski, T. Br J Pharmacol 1971, 43, 649.
21. (a) Pedersen, O. S.; Pedersen, E. B. Synthesis 2000, 479;
22. (b) Cocuzza, A. J.; Chidester, D. R.; Cordova, B. C.; Jeffrey, S.; Parsons, R. L.; Bacheler, L. T.; Erickson-Viitanen, S.; Trainor, G. L.; Ko, S. S. Bioorg Med Chem Lett 2001, 11, 1177.
23. (a) Latif, N.; Mishriky, N.; Massad, F. Aust J Chem 1982, 35, 1037;
24. (b) Skoda, J.; Votruba, I.; Farkas, J. Biochem Pharmacol 1979, 28, 1837.
25. Zhang, P.; Terefenko, E. A.; Fensome, A.; Zhang, Z.; Zhu, Y.; Cohen, J.; Winneker, R.; Wrobel, J.; Yardley, J. Bioorg Med Chem Lett 2002, 12, 787.
26. (a) Agag, T.; Takeichi, T. Macromolecules 2003, 36, 6010;
27. (b) Liu, Y.-L.; Yu, J.-M. J Polym Sci. Part A: Polym Chem 2006, 44, 1890.
28. (a) Burke, W. J. J Am Chem Soc 1949, 71, 609;
29. (b) Burke, W. J.; Kolbezen, M. J.; Stephens, C. W. J Am Chem Soc 1952, 74, 3601;
30. (c) Burke, W. J.; Murdock, K. C.; Ec, G. J Am Chem Soc 1954, 76, 1677;
31. (d) Burke, W. J.; Reynolds, R. J. J Am Chem Soc 1954, 76, 1291;
32. (e) Burke, W. J.; Hammer, C. R.; Weatherbee, C. J Org Chem 1961, 26, 4403;
33. (f) Fields, D. L.; Miller, J. B.; Reynolds, D. D. J Org Chem 1962, 27, 2749;
34. (g) Rivera, A.; Gallo, G. I.; Gayon, M. E. Synth Commun 1994, 24, 2081;
35. (h) Schmidt, C.; Thondorf, I.; Kolehmainen, E.; Bohmer, V.; Vogt, W.; Rissanen, K. Tetrahedron Lett 1998, 39, 8833;
36. (i) Higham, C. S.; Dowling, D. P.; Shaw, J. L.; Cetin, A.; Ziegler, C. J.; Farrell, J. R. Tetrahedron Lett. 2006, 47, 4419;
37. (j) Agag, T.; Takeichi, T. J Polym Sci Part A: Polym Chem 2007, 45, 1878;
38. (k) Burke, W. J.; Smith R. P.; Weatherbee, C. J Am Chem Soc 1952, 74, 602.
39. (a) Miura, S.; Kano, N. Jpn. Pat. 2,000,169,456 (2000);
40. (b) Miura, S.; Kano, N. Chem Abstr 2000, 133, 30736b;
41. (c) Burke, W. J.; Glennie, E. L. M.; Weatherbee, C. J Org Chem 1964, 29, 909;
42. (d) Na, L.; Ling, L.; Fengyun, D.; Yang, Z. Zhanjie 2005, 26, 20.
43. (a) Inoue, S.; Kim, R.; Hoshino, Y.; Honda, K. Chem Commun 2006, 1974.
44. (b) Brunovska, Z.; Liu, J. P.; Ishida, H. Macromol Chem Phys 1999, 200, 1745;
45. (c) Ishida, H. U.S. Pat. 5,543,516 (1996);
46. (d) Ishida, H. Chem Abstr 1996, 124, 203404m;
47. (e) Hossein, F.; Ali, S. Chemistry (Rajkot, India) 2003, 1, 151.
48. Alfonsi, K.; Colberg, J.; Dunn, P. J.; Fevig, T.; Jennings, S.; Johnson, T. A.; Kleine, H. P.; Knight, C.; Nagy, M. A.; Perry, D. A.; Stefaniak, M. Green Chem 2008, 10, 31.
49. (a) Katritzky, A. R.; Xu, Y.-J.; Jain, R. J Org Chem 2002, 67, 8234;
50. (b) Kiskan, B., Yagci, Y.; Sahmetlioglu, E.; Toppare, L. J Polym Sci Part A: Polym Chem 2007, 45, 999;
51. (c) Wang, Y.-X.; Ishida, H. J Appl Polym Sci 2002, 86, 2953.
52. (a) Agag, T. J Appl Polym Sci 2006, 100, 3769;
53. (b) Rincon, J. M. Rev Colomb Quim 1977, 7, 57.