A new multicomponent reaction catalyzed by a Lewis acid catalyst: Convenient synthesis of polyfunctional tetrahydropyrimidines

European Journal of Organic Chemistry

Volumn , Issue 20, 2008, Pages 3519-3523

  Zhang, Min ^a   Jiang, Huan Feng ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Heterocycles; Lewis acids catalysis; Multicomponent reactions; One pot synthesis; Tetrahydropyrimidine

Indexed keywords

EID: 53849112954     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800289     Document Type: Article

References (39)

1. a) A. Pinto, L. Neuville, J. P. Zhu, Angew. Chem. Int. Ed. 2007, 46, 3291-3295;
2. b) D. Bonne, M. Dekhane, J. P. Zhu, Angew. Chem. Int. Ed. 2007, 46, 2485-2488;
3. c) H. Ohno, Y. Ohta, S. Oishi, N. Fujii, Angew. Chem. Int. Ed. 2007, 46, 2295-2298;
4. d) L. Zhang, S. Z. Wang, J. Am. Chem. Soc. 2006, 128, 1442-1443;
5. e) J. Barluenga, A. Diéguez, A. Fernández, F. Rodríguez, F. J. Fañanás, Angew. Chem. Int. Ed. 2006, 45, 2091-2093;
6. f) H. A. Dondas, C. W. G. Fishwich, X. Gai, R. Grigg, C. Kilner, N. Dumrongchai, B. Kongkathip, N. Kongkathip, C. Polysuk, V. Sridharan, Angew. Chem. Int. Ed. 2005, 44, 7570-7574.
7. For recent examples of the formation of C-N bonds in the construction of heterocycles, see: a) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198;
8. b) M. Makosza, K. Wojciechowski, Chem. Rev. 2004, 104, 2631-2666;
9. c) D. Fischer, H. Tomeba, N. Pahadi, N. Patil, Y. Yamamoto, Angew. Chem. Int. Ed. 2007, 46, 4764-4766;
10. d) B. Zou, Q. L. Yuan, D. W. Ma, Angew. Chem. Int. Ed. 2007, 46, 2598-2601;
11. e) Y. Angell, K. Burgess, Angew. Chem. Int. Ed. 2007, 46, 3649-3651;
12. f) T. Jin, Y. Yamamoto, Angew. Chem. Int. Ed. 2007, 46, 3323-3325;
13. g) B. M. Trost, A. McClory, Angew. Chem. Int. Ed. 2007, 46, 2074-2077;
14. h) I. Nakamura, U. Yamagishi, D. Song, S. Konta, Y. Yamamoto, Angew. Chem. Int. Ed. 2007, 46, 2284-2287;
15. i) K. Tanaka, Y. J. Hagiwara, M. Hirano, Angew. Chem. Int. Ed. 2006, 45, 2734-2737;
16. j) V. K. Alexander, A. W. Sromek, V. Gevorgyan, J. Am. Chem. Soc. 2001, 123, 2074-2075.
17. a) M. Zhang, H. F. Jiang, H. L. Liu, Q. H. Zhu, Org. Lett. 2007, 9, 4111-4113;
18. b) M. Zhang, H. F. Jiang, A. Z. Wang, Synlett 2007, 20, 3214-3218.
19. a) W. S. Messer Jr, Y. F. Abuh, Y. Liu, S. Periyasamy, D. O. Ngur, M. A. N. Edgar, A. A. Eissadi, S. Sbeih, P. G. Dunbar, S. Roknich, T. Rho, Z. Fang, B. Ojo, H. Zhang, J. J. Huzl, P. I. Nagy, J. Med. Chem. 1997, 40, 1230-1246;
20. b) W. S. Messer Jr, Y. F. Abuh, K. Ryan, M. A. Shepherd, M. Schroeder, S. Abunada, R. Sehgal, A. A. El-Assadi, Drug Dev. Res. 1997, 40, 171-184;
21. c) H. Zhang, B. Ojo, X. P. Huang, M. A. N. Edgar, A. A. Elssadi, D. Baril, K. Lynch, S. Wahidy, W. S. Messer, Life Sci. 1997, 60, 13-14;
22. d) P. G. Dunbar, G. J. Durant, T. Rho, B. Ojo, J. J. Huzl, D. A. Smith, A. A. El-Assadi, S. Sbeih, D. O. Ngur, S. Periyassamy, W. Hoss, W. S. Messer Jr, J. Med. Chem. 1994, 37, 2774-2782;
23. e) P. G. Dunbar, G. J. Durant, Z. Fang, Y. F. Abuh, M. A. El-Assadi, D. O. Ngur, S. Periyasamy, W. P. Hoss, W. S. Messer Jr, J. Med. Chem. 1993, 36, 842-847;
24. f) G. Malin, R. Iakobashvili, A. Lapidot, J. Biol. Chem. 1999, 274, 6920-6929;
25. g) R. Pattarini, R. J. Smeyne, J. I. Morgan, Neuroscience 2007, 145, 654-668.
26. a) A. Fensome, B. Reinhold, R. Chopra, J. Cohen, M. A. Collins, V. Hudak, K. Malakian, A. Lockhead, A. Olland, K. Svenson, E. A. Terefenko, R. J. Unwalla, J. M. Wilhelm, S. Wilfrom, Y. Zhu, Z. M. Zhang, P. Zhang, R. C. Winnker, J. Wrobel, J. Med. Chem. 2005, 48, 5092-5095;
27. b) H. V. Poel, G. Guillaumet, M. C. V. Massuard, Tetrahedron Lett. 2002, 43, 1205-1208;
28. c) L. Apirat, C. Suwabun, I. Hatsuo, T. Kohji, J. Am. Chem. Soc. 2001, 123, 9947-9955;
29. d) M. Tomasulo, S. Sortino, F. M. Raymo, Org. Lett. 2005, 7, 1109-1112;
30. e) A. Romani, G. Chidichimo, P. Formoso, S. Manfredi, G. Favaro, U. Mazzucato, J. Phys. Chem. B 2002, 106, 9490-9495;
31. f) D. A. Steinhurst, J. C. Owrutsky, J. Phys. Chem. 2001, 105, 3062-3072;
32. g) P. O. J. Scherer, J. Phys. Chem. A 2000, 104, 6301-6307;
33. h) D. A. Steinhurst, A. P. Baronavski, J. C. Owrutsky, J. Phys. Chem. B 2002, 106, 3160-3165;
34. i) C. Seebacher, C. Hellriegel, C. Brauchle, J. Phys. Chem. B 2003, 107, 5445-5452;
35. j) M. Choi, D. Jin, H. Kim, J. Phys. Chem. B 1997, 101, 8092-8097;
36. S. Engleitner, M. Seel, W. Zinth, J. Phys. Chem. A 1999, 103, 3013-3019;
37. k) M. Tomasulo, F. M. Raymo, Org. Lett. 2005, 7, 4633-4636.
38. A mixture of diethyl but-2-ynedioate (1) (170 mg, 1 mmol), aniline (2a) (93 mg, 1 mmol), and DMF (2 mL) was stirred at room temperature for 30 min. After completion of the reaction and purification by preparative TLC, intermediate 5 was obtained as a pure compound.
39. 2 in toluene at 100 °C to form product 4aa.