Microwave assisted efficient one-pot synthesis of 3,5,6-trisubstituted-1,2, 4-triazines from fatty acid hydrazides under solvent-free conditions and their antimicrobial activity

Arkivoc

Volumn 2007, Issue 16, 2007, Pages 137-147

  Rauf, Abdul ^a   Sharma, Shweta ^a   Gangal, Saloni ^a  

^a ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

3,5,6 trisubstituted 1,2,4 triazines; Antimicrobial activity; Fatty acid hydrazides; Microwave irradiation

Indexed keywords

EID: 38149090978     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.g15     Document Type: Article

References (53)

1. (a) Kappe, C. O.; Dallinger, D. Nat. Rev. Drug Discovery 2006, 5, 55.
2. (b) Shipe, W. D.; Wolkenberg, S. E.; Lindsley, C. W. Drug Discovery Today Tech 2005, 2, 155.
3. (c) Leadbeater, N. E. Chem. Commun. 2005, 2881.
4. Caddick, S. Tetrahedron. 1995, 51, 10403.
5. Kidwai, M.; Sapra, P.; Bhushan, K. R.; Saxena R. K.; Gupta, R.; Singh, M. Montash. Chem. 2000, 131, 85.
6. Hermkens , P.; Ottenheijm, H.; Rees, D. Tetrahedron. 1997, 53, 5643.
7. Villemin, D.; Alloumn, A. B. Synth. Commun. 1991, 21, 63.
8. Loupy, A.; Pegion, P.; Ramdani, M.; Jacquault, P. Synth. Commun. 1994, 24 , 1159.
9. Kidwai, M.; Sapra, P. Synth. Commun. 1999, 29, 3237.
10. (a) Geske, G. D.; Wezeman, R. J.; Siegel, A. P.; Blackwell, H. E. J. Am. Chem. Soc. 2005, 127, 12762.
11. (b) Liu, J. -F.; Ye, P.; Sprague, K.; Sargent, K.; Yohannes, D.; Baldino, C. M.; Wilson, C. J.; Ng, S.-C. Org. Lett. 2005, 7, 3363.
12. (c) Liu, J.-F.; Kaselj, M.; Isome, Y.; Chapnick, J.; Zhang, B.; Bi, G.; Yohannes, D.; Yu, L.; Baldino, C. M. J. Org. Chem. 2005, 70, 10488.
13. Boger, D. L. Chem. Rev. 1986, 86, 781.
14. Boger, D. L. Tetrahedron. 1983, 39, 2869.
15. Romanchick, W. A.; Joullie, M. M. Heterocycles. 1978, 9, 1631.
16. Neunhoeffer, H. Comprehensive Heterocyclic Chemistry, Katritzky, A. R. and Rees, C. W.; Eds Pergamon Press; Oxford 1984, 385.
17. Monge, A.; Palop, J.; Ramizrez, C.; Font, F. A. E. Eur. J. Med. Chem. 1991, 26, 83.
18. Labouta, I. M.; Eshba, N. H.; Salama, H. M. Farm. Sci. Ed 1998, 16, 29.
19. Abd. El-Samii, K. J. Chem. Tech. Biotech. 1992, 53, 143.
20. Leach, M. J.; Nobls, M. S. Eur. Pat. Appl. EP459, 829; Chem Abstr. 1992, 116, 128970x.
21. March. L. C.; Bajwa, G. S.; Lee, J.; Wasti, K.; Joullie, M. M. J. Med. Chem. 1976, 19, 845.
22. El-Gendy, Z.; Morsy, J.; Allimony, H.; Abdel-Monem, Abdel, Rehman, R. Phosphorous, Sulphur Silicon and the related Elements. 2003, 178, 2055.
23. Wieczorek, J.; Modarski, M.; Rykowski, A.; Nantka-Nimrski, P. Arch Immunol Ther Exp (Warsz) 1980, 28, 727.
24. Trepanier, D. L.; Wagner, E. R.; Harris, G.; Allan, D. J. Med. Chem. 1966, 9, 881.
25. Srinivas, K.; Srinivas, U.; Jayathirtha, Rao.; Bhanuprakash, K.; Harakishore, K.; Murthy, U.S.N. Bioorg. Med. Chem. Lett. 2005, 15, 1121.
26. Rusinov, V. L.; Ulomskii, E. N.; Chupakhin, O. N.; Zubairnov, M. M.; Kapustin, A. B.; Mitin, n. I.; Zhiravetskii, M. I.; Vinograd, I. A. Pharmaceut. Chem. J. 1990, 24, 640.
27. Gupta, A. S.; Bhattacharya, T.; Hajela, K.; Kripa Shankar, Ahmad, S. Pesticide Science, 1985, 16, 65.
28. Smagin, S. S.; Bogachev, V. E.; Yakubovskii, A. K.; Metkalova, S. E.; Privol'neva, T. P.; Chugunon, V. V.; Lavretskaya, E. F. Pharmaceut. Chem. J. 1975, 9, 222.
29. Rubat, C.; Coudert, P.; Marvel, S.; Fialip, J.; Couquelet, J. J. Pharm. Pharmacol. 1999, 49, 1019.
30. Laasko, P. V., Robinson, R.; Vanderwala, H. P. Tetrahedron. 1957, 1, 103.
31. Metze, R. Chem. Ber. 1955, 88, 772.
32. (a) Metze, R. Chem. Ber. 1956, 89, 2058.
33. (b) Metze, R.; Meyer, S. Chem. Ber. 1957, 90, 481.
34. (c) Metze, R.; Kort, W. Chem. Ber. 1958, 91, 417.
35. Metze, R. Chem. Ber. 1954, 87, 1540.
36. Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1971, 12, 2315.
37. Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron 1977, 33, 1043.
38. Pauddler, W. W.; Barton, J. J. Org. Chem. 1966, 31, 1720.
39. Neuhoeffer, V. H.; Henning, H.; Fruhauf, H. W.; Mutterer, M. Tetrahedron Lett. 1969, 10, 3147.
40. Ohsumi, T.; Neuhoeffer, H. Heterocycles. 1992, 33, 893.
41. (a) Rostamizadeh, R.; Sadeghi, K. Synth. Commun. 2002, 32, 1899.
42. (b) Lindsley, C. W.; Wisnoski, D. D.; Wang, Yi.; Leister, W. H.;Zhao, Z. Tetrahedron Lett., 2003, 44, 4495.
43. (c) Zhao, Z.; Leister, W. H.; Strauss, K. A. Wisnoski, D. D.; Lindsley, C. W. Tetrahedron Lett. 2003, 44, 1123.
44. Mustafa, J.; Ahmad Jr, M. S.; Rauf, A.; Osman, S.M. J. Am. Oil. Chem. Soc. 1984, 61, 555.
45. Rauf, A.; Parveen, H. J. Oleo. Sci. 2004, 53, 279.
46. Agrawal, R.; Rauf, A.; Ahmad, M. J. Am. Oil. Chem. Soc. 1989, 66, 970.
47. (a) Saeed, M. T.; Mustafa, J.; Rauf, A.; Osman, S.M. J. Am. Oil. Chem. Soc. 1992, 69, 481.
48. (b) Saeed, M.T.; Mustafa, J.; Rauf, A.; Osman, S.M. J. Am. Oil. Chem. Soc. 1992, 69, 396.
49. (c) Ansari, M.H.; Saeed, M.T.; Ahmad, M. 1990, J. Chem. Res. Synop, 1990, 126.
50. (d) Rauf, A.; Ahmad, S. J. Chem. Res. 2005, 407.
51. Bauer, A. W.; Kirby W. M. M.; Sherris, J. C.; Turch, M. Am. J. Clin. Path. 1966, 45, 494.
52. Gunstone, F. D., J. Chem. Soc. 1954, 1611.
53. Markley, K. S. Fatty Acids their Chemistry, Properties, Production and Uses. Interscience Publishers, John Wiley and Sons: New York, 1964; Part 3.