Novel and gram-scale green synthesis of flutamide

Synthetic Communications

Volumn 36, Issue 7, 2006, Pages 859-864

  Bandgar, B ^a   Sawant, S ^a  

^a SWAMI RAMANAND TEERTH MARATHWADA UNIVERSITY   (India)

Author keywords

2 methyl N 4 nitro 3 (trifluoromethyl) phenyl propionamide; Cyanuric chloride; Flutamide; Nonsteroidal drug

Indexed keywords

2,4,6 TRIHYDROXY 1,3,5 TRIAZINE; AMIDE; CHLORIDE; DIETHYLAMINE; ESTER; FLUORIDE; FLUTAMIDE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 33644660630     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500464848     Document Type: Article

References (51)

1. (a) Beekwith, A. L. The Chemistry of Amides: Synthesis of Amide; Zabicky, J., Ed.; Interscience: New York, 1970, 96;
2. (b) North, M. Contemp. Org. Synth. 1994, 1, 475.
3. Lai, L. L.; Lin, H. C. Liq. Cryst. 2000, 27, 707.
4. (a) Ravina, E.; Teran, C.; Santana, L.; Garcia, N.; Estevez, I. Heterocycles 1990, 31, 1967;
5. (b) Ohnishi, A.; Ishizaki, E. J. Clin. Pharmacol. 1988, 28, 113;
6. (c) Koo, J.; Avakian, S.; Martin, G. J. J. Am. Chem. Soc. 1955, 77, 5373;
7. (d) Desai, M.; Watthey, J. W. H.; Zuckerman, M. Org. Prep. Proceed. Int. 1976, 8, 85;
8. (e) Butora, G.; Blaha, L.; Rajsner, M.; Helfert, I. Collect. Czech. Chem. Commun. 1992, 57, 1967;
9. (f) Boschi, D.; Stilo, A. D.; Fruttero, R.; Medana, C.; Sorba, G.; Gasco, A. Arch. Pharm. (Weinheim. Ger.) 1994, 327, 661;
10. (g) Althuis, T. H. H.; Hess, H. J. J. Med. Chem. 1977, 20, 146;
11. (h) Manoury, P. M.; Binet, J. L.; Dumas, A. P.; Lefevre-Borg, F.; Cavero, I. J. Med. Chem. 1986, 29, 19;
12. (i) Campell, S. F.; Davey, M. J.; Hardstone, J. D.; Lewis, B. N.; Plamer, M. J. J. Med. Chem. 1987, 30, 49;
13. (j) Hokanen, E.; Pippuri, A.; Kairisalo, P.; Thaller, H.; Kolvisto, M.; Taomi, S. J. Heterocycl. Chem. 1980, 17, 797;
14. (k) Hese, H. J. US Pat. 3,511,836, 1970;
15. (l) Winn, M.; Kyncl, J US Pat. 4093,726, 1978;
16. (m) Campell, S. F. US Pat. 4,188,390, 1980;
17. (n) Manoury, P. N. US Pat. 4,315,007, 1982;
18. (o) Roteman, R. US Pat. 4,251,532, 1981;
19. (p) Igarashi, T. Eur. Pat. 209,089, 1986;
20. (q) Schlager, L. H Eur. Pat. 225,886, 1986;
21. (r) Koning, J Ger. Pat. 3,419,223, 1984.
22. Rasmusson, G. H. Ann. Rep. Med. Chem. 1996, 21, 179.
23. Wang, S.; Liu, X. Hecheng Huaxue 2001, 9(3), 256.
24. Wang, S.; Wang, H.; Yi, Z. Shenyang Yaoke Daxue Xuebao 2000, 17 (1), 38.
25. Konieczny, M.; Potrykus, A. J. Polish Patent 167,850, 1990.
26. Bal'on, Y. G.; Varga, S. V.; Vakulenko, L. I. Khimiko-Farmatserticheskii Zhurnal 1991, 25 (12), 53.
27. Li, J.; Guo, M. Guangdong Yaoxuebao 1995, 11 (2), 74.
28. Xia, P.; Zhou, X.; Shem, Y.; Zheng, Y. Zhongguo Yiyao Congye Zazhi 1989, 20 (8), 341.
29. Neri, R.; Topliss, J. G. Swedish Patent FI 62,058, 1982.
30. Baker, J. W.; Bachman, G. L.; Schumacher, I.; Roman, D. P.; Tharp, A. L. J. Med. Chem. 1967, 10 (1), 93.
31. (a) Falorni, M.; Porcheddu, A.; Toddei, M. Tetrahedron Lett. 1999, 40, 4395;
32. (b) Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taldei, M. J. Org. Chem. 1999, 64, 8962;
33. (c) Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett 2000, 2, 1275;
34. (d) De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534;
35. (e) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 1519;
36. (f) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041;
37. (g) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2002, 4, 553;
38. (h) De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 5152;
39. (i) De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272;
40. (j) Deluca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999.
41. (a) Kumishima, M.; Kawachi, C.; Hioki, K.; Terao, K.; Tani, S. Tetrahedron 2001, 57, 1551;
42. (b) Kunishima, M.; Kawachi, C.; Iwasaki, F.; Terao, K.; Tani, S. Tetrahedron Lett. 1999, 40, 5327;
43. (c) Kunishima, M.; Morita, J.; Kawachi, C.; Iwasaki, F.; Terao, K.; Tani, S. Synlett 1999, 8, 1255;
44. (d) Luo, G.; Xu, L.; Poindexter, G. S. Tetrahedron Lett. 2002, 43, 8909;
45. (e) De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2001, 66, 7907;
46. (f) Kaminska, J. E.; Kaminski, Z. J.; Gora, J. Synthesis 1999, 4, 593;
47. (g) Kaminski, Z. J.; Kolesingka, B.; Markowicz, S. W.; Pokrzeptowicz, K. Polish J. Chem. 1999, 73, 1965;
48. (h) Lee, H.-W.; Kang, T. W.; Cha, K. H.; Kim, E.-N.; Choi, N.-H.; Kim, J.-W.; Hong, C. Synth. Commun. 1999, 28 (8), 1339.
49. Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2002, 43, 3413.
50. Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2003, 44, 2331.
51. Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2003, 44, 3855.