Different N-C-N formation reactions of aromatic aldehydes and thiohydantoins controlled by Lewis acid promoters

Tetrahedron

Volumn 63, Issue 19, 2007, Pages 3973-3981

  Gao, Feifei ^a   Zhang, Guangliang ^a   Zhang, Suoqin ^a   Cheng, Yueming ^a   Shi, Zhan ^a   Li, Yaoxian ^a   Gao, Junlong ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

2 Thiohydantoins; Lewis acids; Multicomponent reactions

Indexed keywords

ACETONITRILE; ALDEHYDE; ALUMINUM CHLORIDE; CARBON; ETHYLENE OXIDE DERIVATIVE; FERRIC CHLORIDE; LEWIS ACID; NITROGEN; THIOHYDANTOIN DERIVATIVE; TITANIUM CHLORIDE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; PRIORITY JOURNAL; SYNTHESIS;

EID: 34047161767     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.002     Document Type: Article

References (42)

1. Dondoni A., and Massi A. Acc. Chem. Res. 39 (2006) 451
2. Nari V., Rajesh C., Vinod A.U., Bindu S., Sreekanth A.R., Mathen J.S., and Balagopal L. Acc. Chem. Res. 36 (2003) 899
3. Dömling A. Chem. Rev. 106 (2006) 17
4. Muccioli G.G., Fazio N., Scriba G.K.E., Poppitz W., Cannata F., Poupaert J.H., Wouters J., and Lambert D.M. J. Med. Chem. 49 (2006) 417
5. Takahashi A., Matsuoka H., Yamada K., and Uda Y. Food Chem. Toxicol. 43 (2005) 521
6. Kandra L., Remenyik J., Batta G., Somsák L., Gyémánt G., and Park K.H. Carbohydr. Res. 340 (2005) 1311
7. Teng X., Degterev A., Jagtap P., Xing X., Choi S., Denu R., Yuan J., and Cuny G.D. Bioorg. Med. Chem. Lett. 15 (2005) 5039
8. Szymańska E., Kieć-Kononowicz K., Białecka A., and Kasprowicz A. Il Farmaco 57 (2002) 39
9. Gyémánt G., Kandra L., Nagy V., and Somsák L. Biochem. Biophys. Res. Commun. 312 (2003) 334
10. Shih R.U., Wu J., Liu Y., Liang Y.C., Lin S.Y., Sheu M.T., and Lee W.S. Biochem. Pharmacol. 67 (2004) 67
11. Tsuda M., Yasuda T., Fukushi E., Kawabata J., Sekiguchi M., Fromont J., and Kobayashi J. Org. Lett. 8 (2006) 4235
12. Chang W.G., Kulkarni M.V., and Sun C.M. J. Comb. Chem. 8 (2006) 141
13. Fuentes J., Salameh B.A.B., Pradera M.A., Córdoba F.J.F., and Gash C. Tetrahedron 62 (2006) 97
14. Beloglazkina E.K., Majouga A.G., Romashkina R.B., and Zyk N.B.V. Tetrahedron Lett. 47 (2006) 2957
15. Nefzi A., Giulianotti M., Truong L., Rattan S., Ostresh J.M., and Houghten R.A. J. Comb. Chem. 4 (2002) 175
16. Lin M.J., and Sun C.M. Tetrahedron Lett. 44 (2003) 8739
17. Roué N., and Bergman J. Tetrahedron 55 (1999) 14729
18. Jakše R., Rečnik S., Golobič A., Golič L., and Stanovnik B. Tetrahedron 57 (2001) 8395
19. Chérouvrier J.R., Carreaux F., and Bazureau J.P. Tetrahedron Lett. 43 (2002) 8745
20. Papeo G., Posteri H., Borghi D., and Varasi M. Org. Lett. 7 (2005) 5641
21. Khodair A.I. Carbohydr. Res. 331 (2001) 445
22. Davis R.A., Aaslbersber W., Meo S., Rocha R.M.D., and Ireland C.M. Tetrahedron 58 (2002) 3263
23. Marton J., Enisz J., Hosztafi S., and Tímár T. J. Agric. Food Chem. 41 (1993) 148
24. Kieć-Kononowicz K., Karolak-Wojciechowska J., Müller C.E., Schumacher B., Pe{ogonek}kala E., and Szymańska E. Eur. J. Med. Chem. 36 (2001) 407
25. Lindel T., and Hoffmann H. Tetrahedron Lett. 38 (1997) 8935
26. Park K.H., and Kurth M.J. J. Org. Chem. 64 (1999) 9297
27. Sim M.M., and Ganesan A. J. Org. Chem. 62 (1997) 3230
28. Severinsen R., Lau J.F., Bondensgaard K., Hansen B.S., Begtrup M., and Ankersen M. Bioorg. Med. Chem. Lett. 14 (2004) 317
29. Zhang W., and Lu Y. Org. Lett. 5 (2003) 2555
30. Elokdah H., Sulkowski T.S., Abou-Gharbia M., Butera J.A., and Chai S.Y. J. Med. Chem. 47 (2004) 681
31. Reyes S., and Burgess K. J. Org. Chem. 71 (2006) 2507
32. Crystal structure of compound 1a has been deposited at the Cambridge Crystallographic Data Center and allocated the reference no. CCDC 611294.
33. Crystal structure of compound 3d has been deposited at the Cambridge Crystallographic Data Center and allocated the reference no. CCDC 619508.
34. Corma A., and García H. Chem. Rev. 103 (2003) 4307
35. Majetich G., Hicks R., Zhang Y., Tian X., Feltman T.L., Fang J., and Duncan Jr. S. J. Org. Chem. 61 (1996) 8169
36. Bartoli G., Bosco M., and Sambri L. Tetrahedron Lett. 38 (1997) 3785
37. Shimada T., Yoshioka M., Konno T., and Ishihara T. Org. Lett. 8 (2006) 1129
38. Ferreira M.J., and Martins A.M. Coord. Chem. Rev. 250 (2006) 118
39. Ritter J.J., and Minieri P.P. J. Am. Chem. Soc. 70 (1948) 4045
40. Top S., and Jaouen G. J. Org. Chem. 46 (1981) 78
41. Zhang Q., Sun S., Hu J., Liu Q., and Tan J. J. Org. Chem. 72 (2007) 139
42. March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 3rd ed. (1985), Wiley Interscience, New York, NY p 862