Synthesis of highly substituted unsymmetrical 1,2-diamines, 1,2-diimines, imidazolium salts and imidazolylidenes by aldimine cross-coupling

Synthesis

Volumn , Issue 21, 2006, Pages 3727-3738

  Kison, Coralie ^a   Opatz, Till ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

1,2 diamines; Carbenes; Cross coupling; Nitrogen heterocycles; Reduction

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; ORGANIC COMPOUNDS; OXIDATION; REACTION KINETICS; REDUCTION;

1,3,4,5-TETRASUBSTITUTED IMIDAZOLIUM SALTS; ALDIMINE CROSS-COUPLING; NITROGEN HETEROCYCLES; NUCLEOPHILIC CARBENES;

SYNTHESIS (CHEMICAL);

1 (4 CHLOROPHENYL) N1,2 DIPHENYL N2 (2 PHENETHYL)ETHANE 1,2 DIAMINE; 1,2 DIIMINE DERIVATIVE; IMIDAZOLE DERIVATIVE; IMIDAZOLYLIDENE DERIVATIVE; N [1 (4 CHLOROPHENYL) 2 (2 PHENYLETHYLIMINO)2 PHENYLETHYLIDENE] 4 METHYLANILINE; N [1 [4 CHLOROPHENYL] 2 (2 PHENYLETHYLIMINO) 2 PHENYLETHYLIDINE] 4 METHYLANILINE; N [2 (BENZHYDRYLIMINO) 1 (4 CHLOROPHENYL) 2 PHENYLETHYLIDENE] 4 METHYLANILINE; N [2 (BENZHYDRYLIMINO) 1,2 DIPHENYLETHYLIDENE] 4 CHLOROANILINE; N [2 (METHYLIMINO) 1 (1 NAPHTHYL) 2 (2 NAPHTHYL)ETHYLIDENE] 4 CHLOROANILINE; N [2 [BENZHYDRYLAMINO 2 CYANO 1,2 DIPHENYLETHYL]BENZENESULFONAMIDE; N [2 [BENZHYDRYLIMINO] 1 (4 CHLOROPHENYL) 2 PHENYLETHYLIDENE]ANILINE; N [2 [BENZHYDRYLIMINO] 1 (4 CHLOROPHENYL) 2 PHENYLETHYLIDINE] 4 METHYLANILINE; N [2 [BENZHYDRYLIMINO] 1,2 DIPHENYLETHYLIDENE] 4 CHLOROANILINE; N [2 [METHYLIMINO] 2 (2 NAPHTHYL) 1 PHENYLETHLIDENE] 4 CHLOROANILINE; N2 BENZHYDRYL 1 (4 CHLOROPHENYL) N1 (METHYLPHENYL) 2 PHENYLETHANE 1,2 DIAMINE; N2 BENZHYDRYL 1 (4 CHLOROPHENYL) N1 PHENYL 2 PHENYLETHANE 1,2 DIAMINE; N2 BENZHYDRYL N1 (4 METHYLPHENYL) 1,2 DIPHENYLETHANE 1,2 DIAMINE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; CYCLIZATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; REDUCTION;

EID: 33751347817     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950237     Document Type: Article

References (63)

1. For an excellent review of the chemistry of 1,2-diamines, see: Lucet, D.; Len Gall, T.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580;
2. Angew. Chem. 1998, 110, 2724.
3. Reedijk, J. Chem. Commun. 1996, 801.
4. Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455.
5. Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233.
6. Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247.
7. Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
8. Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938.
9. Pikul, S.; Corey, E. J. Org. Synth. 1993, 71, 30.
10. Sato, T.; Goto, Y.; Fujisawa, T. Tetrahedron Lett. 1982, 23, 4111.
11. Mukaiyama, T.; Tomimori, K.; Oriyama, T. Chem. Lett. 1985, 813.
12. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
13. Hanessian, S.; Meffre, P.; Girard, M.; Beaudoin, S.; Sancéau, J.-Y.; Bennani, Y. J. Org. Chem. 1993, 58, 1991.
14. Lounasmaa, M.; Hanhinen, P. In The Alkaloids, Vol. 55; Cordell, G., Ed.; Academic Press: New York, 2001, 1-89.
15. Kohmoto, S.; Kashman, Y.; McConnell, O. J.; Rinehart, K. L. Jr.; Wright, A.; Koehn, F. J. Org. Chem. 1988, 53, 3116.
16. Rinehart, K. L.; Kobayashi, J.; Harbour, G. C.; Hughes, R. G. Jr.; Mizsak, S. A.; Scahill, T. A. J. Am. Chem. Soc. 1984, 106, 1524.
17. Gasc, M. B.; Lattes, A.; Perie, J. J. Tetrahedron 1983, 39, 703.
18. Moriarty, R. M.; Khosrowshahi, J. S. Tetrahedron Lett. 1986, 27, 2809.
19. Sharpless, K. B.; Chong, A. O.; Oshima, K. J. Org. Chem. 1976, 41, 177.
20. Feit, P. W.; Nielsen, O. T. J. Med. Chem. 1967, 10, 927.
21. VanderWerf, R.; Heisler, R. Y.; McEwen, W. E. J. Am. Chem. Soc. 1954, 76, 1231.
22. von Miller, W.; Plöchl, J. Ber. Dtsch. Chem. Ges. 1892, 25, 2020.
23. Khan, N. H.; Zuberi, R. H.; Siddiqui, A. A. Synth. Commun. 1980, 10, 363.
24. Bernardi, L.; Bonini Bianca, F.; Capito, E.; Dessole, G.; Comes-Franchini, M.; Fochi, M.; Ricci, A. J. Org. Chem. 2004, 69, 8168.
25. Kise, N.; Kashiwagi, K.; Watanabe, M.; Yoshida, J. J. Org. Chem. 1996, 61, 428.
26. Meyer, N.; Opatz, T. Synlett 2003, 1427.
27. Meyer, N.; Opatz, T. Synlett 2004, 787.
28. Meyer, N.; Werner, F.; Opatz, T. Synthesis 2005, 945.
29. Kison, C.; Meyer, N.; Opatz, T. Angew. Chem. Int. Ed. 2005, 44, 5662;
30. Angew. Chem. 2005, 117, 5807.
31. For the addition of a deprotonated Reissert-compound to an imine, see: Kant, J. J. Heterocycl. Chem. 1990, 27, 2129.
32. CCDC 601965 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
33. Reich, B. J. E.; Greenwald, E. E.; Justice, A. K.; Beckstead, B. T.; Reibenspies, J. H.; North, S. W.; Miller, S. A. J. Org. Chem. 2005, 70, 8409.
34. Becker, H.-D. J. Org. Chem. 1970, 35, 2099.
35. Strain, H. H. J. Am. Chem. Soc. 1928, 50, 2218.
36. Walia, J. S.; Guillot, L.; Singh, J.; Chatta, M. S.; Satyanarayana, M. J. Org. Chem. 1972, 37, 135.
37. Reich, B. J. E.; Justice, A. K.; Beckstead, B. T.; Reibenspies, J. H.; Miller, S. A. J. Org. Chem. 2004, 69, 1357.
38. Jaunin, R.; Courbat, P. Helv. Chim. Acta 1961, 44, 309.
39. Ohtaka, S.; Mori, K.; Uemura, S. Heteroat. Chem. 2001, 12, 309.
40. Periasamy, M.; Srinivas, G.; Karunakar, G. V.; Bharathi, P. Tetrahedron Lett. 1999, 40, 7577.
41. Mangeney, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, J. Synthesis 1988, 255.
42. Hatano, B.; Ogawa, A.; Hirao, T. J. Org. Chem. 1998, 63, 9421.
43. Largeron, M.; Fleury, M.-B. J. Org. Chem. 2000, 65, 8874.
44. Lu, Z.-H.; Bhongle, N.; Su, X.; Ribe, S.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 8617.
45. Glorius, F.; Altenhoff, G.; Goddard, R.; Lehmann, C. Chem. Commun. 2002, 2704. This method yields imidazolium triflates which are more soluble in nonpolar solvents than the corresponding chlorides.
46. Arduengo, A. J. III; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523.
47. Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
48. Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204.
49. For a review on stable carbenes, see: Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
50. For a review on N-heterocyclic carbenes in catalysis, see: Hermann, W. A. Angew. Chem. Int. Ed. 2002, 42, 1290;
51. Angew. Chem. 2002, 114, 1342.
52. Hassan, N. A.; Bayer, E.; Jochims, J. C. J. Chem. Soc., Perkin Trans. 1 1998, 3747.
53. Leblanc, J.-P.; Gibson, H. W. J. Org. Chem. 1994, 59, 1072.
54. Ranu, B. C.; Dey, S. S.; Hajra, A. Tetrahedron 2002, 58, 2529.
55. Maccarone, E.; Mamo, A.; Musumarra, G.; Scarlata, G.; Tomaselli, G. A. J. Org. Chem. 1977, 42, 3024.
56. Tsuge, O.; Koga, M.; Shinkai, I. Tetrahedron 1973, 29, 259.
57. Hess, U.; Thiele, R. J. Prakt. Chem. 1982, 324, 385.
58. Mesli, A.; Tirouflet, J. Bull. Soc. Chim. Fr. 1975, 1753.
59. Cavallito, C. J.; Yun, H. S.; Edwards, M. L.; Foldes, F. F. J. Med. Chem. 1971, 14, 130.
60. Prot, T. Rocz. Chem. 1971, 45, 247;
61. Chem. Abstr. 1971, 75, 26791g.
62. Davis, F. A.; Lamendola, J.; Nadir, U.; Kluger, E. W.; Sedergran, T. C.; Panunto, T. W.; Billmers, R.; Jenkins, R.; Turchi, I. J.; Watson, W. H.; Chen, J. S.; Kimura, M. J. Am. Chem. Soc. 1980, 102, 2000.
63. Dupont, J.; Suarez, P. A. Z.; De Souza, R. F.; Burrow, R. A.; Kintzinger, J.-P. Chemistry 2000, 6, 2377.