Me3SiCl-promoted intramolecular cyclization of aromatic compounds tethered with N,O-acetals leading to the facile preparation of 1,4-benzodiazepine skeletons

Tetrahedron

Volumn 66, Issue 46, 2010, Pages 8837-8845

  Sakai, Norio ^a   Watanabe, Akimasa ^a   Ikeda, Reiko ^a   Nakaike, Yumi ^a   Konakahara, Takeo ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

1,4 Benzodiazepine; Chlorosilane; Intramolecular cyclization; N,O Acetal

Indexed keywords

1,4 BENZODIAZEPINE; 2 (INDOLIN 1 YL) N METHOXYMETHYL N METHYLETHYLAMINE; ACETAL DERIVATIVE; ANILINE DERIVATIVE; BENZODIAZEPINE; CHLOROTRIMETHYLSILANE; N [CARBOMETHOXY(METHOXY)METHYL] 2 (INDOLIN 1 YL) N METHYLETHYLAMINE; N [CARBOMETHOXY(METHOXY)METHYL] N METHYL 2 (1,2,3,4 TETRAHYDROQUINOLIN 1 YL)ETHYLAMINE; N [CARBOMETHOXY(METHOXY)METHYL] N PROPYL 2 [(3 N,N DIETHYL)PHENOXY]ETHYLAMINE; N [CARBOMETHOXY(METHOXY)METHYL] N' ETHYL N METHYL N' PHENYLETHYLAMINE; N [CARBOMETHOXY(METHOXY)METHYL] N,N' DIMETHYL N' (3 TRIFLUOROMETHYLPHENYL)ETHYLAMINE; N [CARBOMETHOXY(METHOXY)METHYL] N,N' DIMETHYL N' (4 METHOXYPHENYL)ETHYLAMINE; N [CARBOMETHOXY(METHOXY)METHYL] N,N' DIMETHYL N' (4 METHYLPHENYL)ETHYLAMINE; N [CARBOMETHOXY(METHOXY)METHYL] N,N' DIMETHYL N' PHENYLETHYLAMINE; N ALKYL 2 OXAZOLIDINONE DERIVATIVE; N ALKYLANILINE; N ALLYL N' ETHYL N METHOXYMETHYL N' PHENYLETHANE 1,2 DIAMINE; N BUTYL N [CARBOMETHOXY(METHOXY)METHYL] 2 [(4 METHOXY)PHENOXY]ETHYLAMINE; N METHOXYMETHYL N METHYL 2 (1,2,3,4 TETRAHYDROQUINOLIN 1 YL)ETHYLAMINE; N' BENZYL N [CARBOMETHOXY(METHOXY)METHYL] N METHYL N' PHENYLETHYLAMINE; N' ETHYL N METHOXYMETHYL N METHYL N' PHENYLETHANE 1,2 DIAMINE; N,N' DIMETHYL N METHOXYMETHYL N' (2 METHYLPHENYL)ETHANE 1,2 DIAMINE; N,N' DIMETHYL N METHOXYMETHYL N' (3 TRIFLUOROMEHYLPHENYL)ETHANE 1,2 DIAMINE; N,N' DIMETHYL N METHOXYMETHYL N' (4 CHLOROPHENYL)ETHANE 1,2 DIAMINE; N,N' DIMETHYL N METHOXYMETHYL N' (4 FLUOROPHENYL)ETHANE 1,2 DIAMINE; N,N' DIMETHYL N METHOXYMETHYL N' (4 METHOXYPHENYL)ETHANE 1,2 DIAMINE; N,N' DIMETHYL N METHOXYMETHYL N' (4 METHYLPHENYL)ETHANE 1,2 DIAMINE; N,N' DIMETHYL N METHOXYMETHYL N' PHENYLETHANE 1,2 DIAMINE; N,O ACETAL DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 77958163511     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.077     Document Type: Article

References (60)

1. L.H. Sternbach J. Med. Chem. 22 1979 1 and references cited therein
2. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893
3. D. Hadjipavlou-Litina, R. Garg, and C. Hansch Chem. Rev. 104 2004 3751
4. For selected papers, see:
5. E.C. Clement, and P.R. Carlier Tetrahedron Lett. 46 2005 3633
6. C. Kalinski, M. Umkehrer, G. Ross, J. Kolb, C. Burdack, and W. Hiller Tetrahedron Lett. 47 2006 3423
7. T. Deschrijver, P. Verwilst, K. Broos, H. Deckmyn, W. Dehaen, and W.M. De Borggraeve Tetrahedron 65 2009 4521
8. For selected papers, see:
9. M. Uskokovic, J. Iacobelli, and W. Wenner J. Org. Chem. 27 1962 3606
10. A.A. Santilli, and T.S. Osdene J. Org. Chem. 29 1964 1998
11. G.E. Hardtmann, and H. Ott J. Org. Chem. 34 1969 2244
12. M.A. Weidner-Wells, A. DeCamp, and P.H. Mazzocchi J. Org. Chem. 54 1989 5746
13. C.G. Boojamra, K.M. Burow, and J.A. Ellman J. Org. Chem. 60 1995 5742
14. C.G. Boojamra, K.M. Burow, L.A. Thompson, and J.A. Ellman J. Org. Chem. 62 1997 1240
15. Y. Pei, M.J. Lilly, D.J. Owen, L.J. D'Souza, X.-Q. Tang, J. Yu, R. Nazarbaghi, A. Hunter, C.M. Anderson, S. Glasco, N.J. Ede, I.W. James, U. Maitra, S. Chandrasekaran, W.H. Moos, and S.S. Ghosh J. Org. Chem. 68 2002 92
16. A. Kamal, A.V. Ramana, K.S. Reddy, K.V. Ramana, A. Hari Babu, and B.R. Prasad Tetrahedron Lett. 45 2004 8187
17. R.S. Al-awar, J.E. Ray, K.A. Hecker, S. Joseph, J. Huang, C. Shih, H.B. Brooks, C.D. Spencer, S.A. Watkins, R.M. Schultz, E.L. Considine, M.M. Faul, K.A. Sullivan, S.P. Kolis, M.A. Carr, and F. Zhang Bioorg. Med. Chem. Lett. 14 2004 3925
18. S. Marcaccini, M. Miliciani, and R. Pepino Tetrahedron Lett. 46 2005 711
19. K. Hemming, and C. Loukou Tetrahedron 60 2004 3349
20. For a selected paper, see: E.M. Beccalli, G. Broggini, G. Paladino, and C. Zoni Tetrahedron 61 2005 61
21. For selected papers, see:
22. L.H. Sternbach, and E. Reeder J. Org. Chem. 26 1961 1111
23. L.H. Sternbach, and E. Reeder J. Org. Chem. 26 1961 4936
24. L.G. Hamann, C.Z. Ding, A.V. Miller, C.S. Madsen, P. Wang, P.D. Stein, A.T. Pudzianowski, D.W. Green, H. Monshizadegan, and K.S. Atwal Bioorg. Med. Chem. Lett. 14 2004 1031
25. For selected papers, see:
26. M. Gates J. Org. Chem. 45 1980 1675
27. R.G. Sherrill, and E.E. Sugg J. Org. Chem. 60 1995 730
28. S. Herrero, M.T. Garcia-Lopez, E. Cenarruzabeitia, J. Del Rio, and R. Herranz Tetrahedron 59 2003 4491
29. S. Herrero, M.T. Garcia-Lopez, and R. Herranz J. Org. Chem. 68 2003 4582
30. P. Wiklund, M. Rogers-Evans, and J. Bergman J. Org. Chem. 69 2004 6371
31. T. Hussenether, H. Hübner, P. Gmeiner, and R. Troschütz Bioorg. Med. Chem. 12 2004 2625
32. S. Ferrini, F. Ponticelli, and M. Taddei J. Org. Chem. 71 2006 9217
33. For selected papers, see:
34. S. Archer, T.R. Lewis, M.J. Unser, J.O. Hoppe, and H. Lape J. Am. Chem. Soc. 79 1957 5783
35. G.A. Kraus, and S. Yue J. Org. Chem. 48 1983 2936
36. S. Massa, A. Mai, M. Artico, F. Corelli, and M. Botta Tetrahedron 45 1989 2763
37. A.R. Katritzky, Y.-J. Xu, and H.-Y. He J. Chem. Soc., Perkin Trans. 1 2002 592
38. A. Cul, A. Daich, B. Decroix, G. Sanz, and L. Van Hijfte Tetrahedron 60 2004 11029
39. For selected papers, see:
40. G.S. Welmaker, and J.E. Sabalski Tetrahedron Lett. 45 2004 4851
41. M.A.J. Duncton, L.M. Smith, S. Burdzovic-Wizeman, A. Burns, H. Liu, Y. Mao, W.C. Wong, and A.S. Kiselyov J. Org. Chem. 70 2005 9629
42. X. Che, L. Zheng, Q. Dang, and X. Bai Tetrahedron 62 2006 2563
43. For a selected paper, see: M. Ishikura, M. Mori, T. Ikeda, M. Terashima, and Y. Ban J. Org. Chem. 47 1982 2456
44. For selected papers, see:
45. M.T. Hancock, R.E. Minto, and A.R. Pinhas Tetrahedron Lett. 44 2003 8357
46. J.-Y. Wang, X.-F. Guo, D.-X. Wang, Z.-T. Huang, and M.-X. Wang J. Org. Chem. 73 2008 1979
47. For selected papers, see:
48. G.A. Kraus, and H. Maeda Tetrahedron Lett. 35 1994 9189
49. H.J. Breslin, M.J. Kukla, D.W. Ludovici, R. Mohrbacher, W. Ho, M. Miranda, J.D. Rodgers, T.K. Hitchens, and G. Leo J. Med. Chem. 38 1995 771
50. X.L. Wang, X.F. Zheng, R.H. Liu, J. Reiner, and J.B. Chang Tetrahedron 63 2007 3389
51. N. Sakai, T. Hamajima, and T. Konakahara Tetrahedron Lett. 43 2002 4821
52. N. Sakai, M. Hirasawa, T. Hamajima, and T. Konakahara J. Org. Chem. 68 2003 483
53. N. Sakai, J. Asano, Y. Shimano, and T. Konakahara Synlett 2007 2675
54. N. Sakai, J. Asano, Y. Shimano, and T. Konakahara Tetrahedron 64 2008 9208
55. N. Sakai, A. Sato, and T. Konakahara Synlett 2009 1449
56. N. Sakai, J. Asano, Y. Kawada, and T. Konakahara Eur. J. Org. Chem. 2009 917
57. G.S. Poindexter, D.A. Owens, P.L. Dolan, and E. Woo J. Org. Chem. 57 1992 6257
58. Aqueous isolation and silica gel purification of the acetals having an ester resulted in decomposition of the N,O-acetals.
59. When the intramolecular reaction of 1a was performed with 1.2 equiv of HCl or 0.6 equiv of TMSCl, the benzodiazepine 4a was obtained in 49 or 48% yields, respectively. The results show that a stoichiometric amount of a relatively weak Lewis acid TMSCl functions as the best promoter. In this context, one reviewer suggests NMR monitoring of interaction between N,O-acetal 1a and TMSCl. However, we could not observe such results.
60. 3SiCl. Although there are no clear explanations, it seems that the product yield involves an error in experimental handling. However, the important point in the results is that HCl functions as a catalyst to promote the intramolecular cyclization.