Synthesis of novel tricyclic pyrimidine-fused 5,6-dihydrobenzodiazepines via a Pictet-Spengler-like cyclization

Tetrahedron

Volumn 62, Issue 11, 2006, Pages 2563-2568

  Che, Xin ^a   Zheng, Lianyou ^a   Dang, Qun ^a   Bai, Xu ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

Aldehyde; Benzodiazepines; Pyrimidines

Indexed keywords

4 CHLORO 11 METHYL 6 (4' FLUOROPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 11 METHYL 6 (4' METHYLPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 11 METHYL 6 (4' NITROPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 11 METHYL 6 ETHYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 11 METHYL 6 PHENYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 11 METHYL 6 PROPYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 8 FLUORO 11 METHYL 6 PHENYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 8,11 DIMETHYL 6 (4' FLUOROPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 8,11 DIMETHYL 6 (4' METHYLPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 8,11 DIMETHYL 6 (4' NITROPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 8,11 DIMETHYL 6 ETHYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4] BENZODIAZEPINE; 4 CHLORO 8,11 DIMETHYL 6 PHENYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 8,11 DIMETHYL 6 PROPYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 9,11 DIMETHYL 6 (4' FLUOROPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 9,11 DIMETHYL 6 (4' METHYLPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 9,11 DIMETHYL 6 (4' NITROPHENYL) 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 9,11 DIMETHYL 6 ETHYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4] BENZODIAZEPINE; 4 CHLORO 9,11 DIMETHYL 6 PHENYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 4 CHLORO 9,11 DIMETHYL 6 PROPYL 5,6 DIHYDROPYRIMIDO[4,5 B][1,4]BENZODIAZEPINE; 5 AMINO 6 CHLORO 4 (N METHYLANILINO)PYRIMIDINE; 6 CHLORO 8,9 DIPHENYL 8,9 DIHYDRO 7H PURINE; ALDEHYDE; ANILINE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PICTET SPENGLER REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 32644451775     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.042     Document Type: Article

References (25)

1. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893 930
2. L. Abrous, J. Hynes Jr., S.R. Friedrich, A.B. Smith, and R. Hirschmann Org. Lett. 3 2001 1089 1092
3. B.E. Evans, K.E. Rittle, M.G. Bock, R.M. DiPardo, R.M. Freidinger, W.L. Whitter, G.F. Lundell, D.F. Veber, P.S. Anderson, R.S.L. Chang, V.J. Lotti, D.J. Cerino, T.B. Chen, P.J. Kling, K.A. Kunkel, J.P. Springer, and J. Hirshfield J. Med. Chem. 31 1988 2235 2246
4. B. Evans, A. Pipe, L. Clark, and M. Banks Bioorg. Med. Chem. Lett. 11 2001 1297 1300
5. P.G. Wyatt, M.J. Allen, J. Chilcott, G. Hickin, N.D. Miller, and P.M. Woollard Bioorg. Med. Chem. Lett. 11 2001 1301 1305
6. S.Y. Stevens, B.A. Bunin, M.J. Plunkett, P.C. Swanson, J.A. Ellman, and G.D. Glick J. Am. Chem. Soc. 118 1996 10650 10651
7. J. Yang, Q. Dang, J. Liu, Z. Wei, J. Wu, and X. Bai J. Comb. Chem. 7 2005 474 482
8. B. Lucas, N. Rosen, and G. Chiosis J. Comb. Chem. 3 2001 518 520
9. S. Ding, N.S. Gray, Q. Ding, X. Wu, and P.G. Schultz J. Comb. Chem. 4 2002 183 186
10. A.G. Takvorian, and A.P. Combs J. Comb. Chem. 6 2004 171 174
11. R.D. Lucrezia, I.H. Gilbert, and C.D. Floyd J. Comb. Chem. 2 2000 249 253
12. J. Liu, Q. Dang, Z. Wei, H. Zhang, and X. Bai J. Comb. Chem. 7 2005 627 636
13. M. Hocek Eur. J. Org. Chem. 2 2003 245 254
14. A. Gangjee, X. Lin, and S.F. Queener J. Med. Chem. 47 2004 3689
15. Q. Dang, and J.E. Gomez-Galeno J. Org. Chem. 67 2002 8703 8705
16. P. Bhuyan, R.C. Boruah, and J.S. Sandhu J. Org. Chem. 55 1990 568 571
17. S. Selleri, F. Bruni, C. Costagli, A. Costanzo, G. Guerrini, G. Ciciani, P. Gratteri, C. Bonaccini, P.M. Aiello, F. Besnard, S. Renad, B. Costa, and C. Martini J. Med. Chem. 46 2003 310 313
18. A.J. Thskur, P. Saikia, D. Prajapati, and J.S. Sandhu Synlett 2001 1299 1302
19. K.S. Gudmundsson, and B.A. Johns Org. Lett. 5 2003 1369
20. A. Gangjee, Y. Zeng, J.J. McGuire, F. Mehraein, and R.L. Kisliuk J. Med. Chem. 47 2004 6893 6901
21. J. Yang, X. Che, Q. Dang, Z. Wei, and X. Bai Org. Lett. 7 2005 1541 1543
22. E.D. Cox, and J.M. Cook Chem. Rev. 95 1995 1797 1842
23. M. Arend, B. Westermann, and M. Risch Angew. Chem., Int. Ed. 37 1998 1045 1070
24. During the review of this manuscript, a similar strategy was reported by another group: (a) Y.-J. Xu, H. Liu, W. Pan, X. Chen, W.C. Wong, and M. Labelle Tetrahedron Lett. 46 2005 7523 7526
25. M.A.J. Duncton, L.M. Smith II, S. Burdzovic-Wizeman, A. Burns, H. Liu, Y. Mao, W.C. Wong, and A.S. Kiselyov J. Org. Chem. 70 2005 9629 9631