Reinvestigating the synthesis of N-arylbenzamidines from benzonitriles and anilines in the presence of AlCl3

Tetrahedron

Volumn 66, Issue 27-28, 2010, Pages 5134-5139

  Koutentis, Panayiotis A ^a   Mirallai, Styliana I ^a  

^a UNIVERSITY OF CYPRUS   (Cyprus)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO (N PHENYL)BENZAMIDINE; 2 AMINO N (3,4 DICHLOROPHENYL)BENZAMIDINE; 2 AMINO N (4 BROMOPHENYL)BENZAMIDINE; 2 AMINO N (4 CHLOROPHENYL)BENZAMIDINE; 2 AMINO N (4 FLUOROPHENYL)BENZAMIDINE; 2 AMINO N (4 METHOXYPHENYL)BENZAMIDINE; 2 AMINO N (4 METHYLPHENYL)BENZAMIDINE; ALUMINUM CHLORIDE; ANILINE DERIVATIVE; BENZAMIDINE DERIVATIVE; BENZONITRILE; LEWIS ACID; N (3,4 DICHLOROPHENYL)BENZAMIDINE; N (4 BROMOPHENYL)BENZAMIDINE; N (4 CHLOROPHENYL)BENZAMIDINE; N (4 FLUOROPHENYL)BENZAMIDINE; N (4 IODOPHENYL)BENZAMIDINE; N (4 METHOXYPHENYL)BENZAMIDINE; N (4 METHYLPHENYL)BENZAMIDINE; N PHENYLBENZAMIDINE; N(4 NITROPHENYL)BENZAMIDINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77954348470     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.103     Document Type: Article

References (58)

1. (a) Liebscher, J.; Feist, K. J. Prakt. Chem. (Leipzig) 1988, 330,175
2. (b) Guillemet, M.; Robert, A.; Baudy-Floc'h, M. Tetrahedron Lett. 1995,36,547
3. (c) Wiglenda, T.; Ott, I.; Kircher, B.; Schumacher, P.; Schuster, D.; Langer, T.; Gust, R. J. Med. Chem. 2005, 48, 6516
4. (d) Wiglenda, T.; Gust, R. J. Med. Chem. 2007, 50, 1475
5. (e) Sharma, A. K.; Mazumdar, S. N.; Mahajan, M. P. J. Chem. Soc., Perkin Trans. 11997, 3065
6. (f) Guinamant, J. L.; Robert, A. Tetrahedron 1986,42,1169
7. (g) Sewald, N.; Burger, K. Monatsh. Chem. 1993,124, 899.
8. (a) Ramsden, C. A.; Rose, H. L. J. Chem. Soc., Perkin Trans. 1 1995, 615
9. (b) Ramsden, C. A.; Rose, H. L. J. Chem. Soc., Perkin Trans. 1 1997, 2319.
10. Il'chenko, A. Y.; Krokhtyak, V. I.; Yagupol'skii, L. M. Chem. Heterocycl. Compd. (N. Y.) 1981, 17,1236.
11. (a) Robev, S. K. Tetrahedron Lett. 1983,24,4351
12. (b) Nair, M. D.; Desai, J. A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. 1980, 19, 20
13. (c) Szczepankiewicz, W.; Suwinski, J.; Bujok, R. Tetrahedron 2000, 56, 9343
14. (d) Bedi, P. M. S.; Kumar, V.; Mahajan, M. P. Bioorg. Med. Chem. Lett. 2004,14,5211
15. (e) Kumar, V.; Mohan, C.; Gupta, M.; Mahajan, M. P. Tetrahedron 2005, 61, 3533.
16. Etienne, A.; Le Berre, A.; Giorgett, J. P. Bull. Soc. Chim. Fr. 1973, 985.
17. (a) Kresze, G.; Seyfried, C.; Trede, A. Liebigs Ann. 1968, 715, 223
18. (b) Finch, N.; Ricca, S., Jr.; Werner, L. H.; Rodebaugh, R. J. Org. Chem. 1980, 45, 3416
19. (c) Gil-christ, T. L.; Rees, C. W.; Vaughan, D. J. Chem. Soc., Perkin Trans. 1 1983, 49
20. (d) Levchenko, E. S.; Borovikova, G. S.; Borovik, E. I.; Kalinin, V. N. J. Org. Chem. USSR 1984, 20, 176
21. (e) Zienkiewicz, J.; Kaszynski, P.; Young, V. G., Jr. J. Org. Chem. 2004, 69, 2551
22. (f) Zienkiewicz, J.; Fryszkowska, A.; Zienkiewicz, K.; Guo, F.; Kaszynski, P.; Januszko, A.; Jones, D. J. Org. Chem. 2007, 72, 3510.
23. Szczepankiewicz, W.; Suwinski, J.; Karczmarzyk, Z. Chem. Heterocycl. Compd., (N. Y.) 2004, 40, 801.
24. Schmidpeter, A.; Bansal, R. K.; Karaghiosoff, K.; Steinmuller, F.; Spindler, C. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 49/50, 349.
25. Capuano, L.; Fischer, W.; Scheidt, H.; Schneider, M. Chem. Ber. 1978,111, 2497.
26. Shermolovich, Y. G.; Talanov, V. S.; Pirozhenko, V. V.; Markovskii, L. N. Russ. J. Org. Chem. 1982, 18, 2240.
27. (a) Asano, T.; Yoshikawa, T.; Nakamura, H.; Uehara, Y.; Yamamoto, Y. Bioorg. Med. Chem. Lett. 2004,14,2299
28. (b) Asano, T.; Yoshikawa, T.; Usui, T.; Yamamoto, H.; Yamamoto, Y.; Uehara, Y.; Nakamura, H. Bioorg. Med. Chem. 2004, 12, 3529
29. (c) Nakamura, H.; Sasaki, Y.; Uno, M.; Yoshikawa, T.; Asano, T.; Ban, H. S.; Fu-kazawa, H.; Shibuya, M.; Uehara, Y. Bioorg. Med. Chem. Lett. 2006, 16, 5127.
30. Gentile, R.J.; Murray, R.J.; MacDonald, J.E.; Shakespeare, W.C. U.S. Patent 5,807,885 1998.
31. Burnett, D.A.; Wu, W.-L.; Domalski, M.S.; Caplen, M.A.; Spring, R.; Lachowicz, J.E., U.S. Patent 7,423,149 2008.
32. (a) Stephens, C. E.; Tanious, F.; Kim, S.; Wilson, W. D.; Schell, W. A.; Perfect, J. R.; Franzblau, S. G.; Boykin, D. W. J. Med. Chem. 2001, 44,1741
33. (b) Stephens, C. E.; Brun, R.; Salem, M. M.; Werbovetz, K. A.; Tanious, F.; Wilson, W. D.; Boykin, D. W. Bioorg. Med. Chem. Lett. 2003, 13, 2065
34. (c) Arafa, R. K.; Brun, R.; Werbovetz, K. A.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. Heterocycl. Commun. 2004,10, 423
35. (d) de Souza, E. M.; Lansiaux, A.; Bailly, C.; Hu, W. D.; Wilson, Q.; Boykin, D. W.; Batista, M. M.; Araujo-Jorge, T. C.; Soeiro, M. N. C. Biochem. Pharmacol. 2004, 68, 593.
36. Shukla, J. S.; Rastogi, R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1981, 20, 1072.
37. (a) Dunn, P. J. In Comprehensive Functional Group Transformations II; Jones, R. C. F., Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier: Oxford, UK, 2005; Vol. 5; Chapter 5.19, p 655
38. (b) Soll, H. Methoden Org. Chem. (Houben-Weyl) 1958, 9,39
39. (c) Gautier, J.-A.; Miocque, M.; Farnoux, C. C. In The Chemistry of Amidines and Imidates; Patai, S., Ed.; Wiley: New York, NY, 1975; Vol. 1, p 283.
40. Hitchcock, P. B.; Lappert, M. F.; Merle, P. G. Dalton Trans. 2007, 585.
41. (a) Gautier, J.-A.; Miocque, M.; Fauran, C.; Le Cloareg, A.-Y. Bull. Soc. Chim. Fr. 1970, 1, 200
42. (b) Daoust, B.; Lessard, J. Can. J. Chem. 1995, 73, 362.
43. Pinner, A.; Klein, F. Ber. 1877, 10,1889.
44. (a) Oxley, P.; Partridge, M. W.; Short, W. F.J. Chem. Soc. 1947,1110
45. (b) Liberman, S.; Tsatsas, G.; Delaby, R. Bull. Soc. Chim. Fr. 1958,185.
46. (c) Cooper, F. C.; Partridge, M. W. Org. Synth. 1963, 36, 64
47. (d) Pan, K.; Scott, M. K.; Lee, D. H. S.; Fitzpatrick, L. J.; Crooke, J. J.; Rivero, R. A.; Rosenthal, D. I.; Vaidya, A. H.; Boyu Zhao, B.; Reitz, A. B. Bioorg. Med. Chem. 2003, 11, 185.
48. Wang, J.; Xu, F.; Cai, T.; Shen, Q. Org. Lett. 2008,10, 445.
49. (a) Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801.
50. (b) Kuznetsov, M. L. Rus. Chem. Rev. 2002, 71, 265.
51. Asproni, B.; Pau, A.; Bitti, M.; Melosu, M.; Cerri, R.; Dazzi, L.; Seu, E.; Maciocco, E.; Sanna, E.; Busonero, F.; Talani, G.; Pusceddu, L.; Altomare, C.; Trapani, G.; Biggio, G. J. Med. Chem. 2002, 45, 4655.
52. Cooper, F. C.; Partridge, M. W. J. Chem. Soc. 1954, 3429.
53. Ponomarev, I. I.; Vinogradova, S. V. Russ. Chem. Bull. 1990, 39, 2229.
54. Cloez, S. LiebigsAnn. 1860, 115, 23.
55. Oxley, P.; Short, W. F. J. Chem. Soc. 1949, 449.
56. Barber, H. J. J. Chem. Soc. 1943,101.
57. Kalashnikova, N. A.; Kulbitsk, G. N.; Passet, B. V.; Askinazi, B. Z. J. Org. Chem. USSR (English Transl) 1974, 10,1539.
58. Sevcik, V. Acta Univ. Palacki. Olom., Fac. Rerum Natur. 1973, 41, Chemica 13,131.