Solid-phase synthesis of benzimidazole N-oxides on SynPhase™ Lanterns

Tetrahedron Letters

Volumn 44, Issue 11, 2003, Pages 2293-2296

  Wu, Zemin ^a   Ede, Nicholas J ^a   Mathieu, Marc N ^a  

^a Mimotopes Pty Ltd   (Australia)

Author keywords

Benzimidazole N oxide; Solid phase synthesis; SynPhase Lantern

Indexed keywords

BENZIMIDAZOLE; BENZODIAZEPINE DERIVATIVE; CARBONYL DERIVATIVE; ETHINYLESTRADIOL PLUS NORETHISTERONE; OXIDE;

ARTICLE; CHEMICAL PROCEDURES; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIBRARY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SOLID; SYNTHESIS;

EID: 0037430683     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00275-2     Document Type: Article

References (13)

1. Smith, D. M.; Tennant, G. In Benzimidazoles and Congeneric Tricyclic Compounds; Preston, P. N., Ed. Benzimidazole-N-oxides. John Wiley & Sons: New York, 1982; Chapter 2.
2. Ellsworth, R. L.; Hinkley, D. F.; Schoenewaldt, E. F. French Patent No. FR 2014422, 1970.
3. Baylina, G. E.; Llobet, P. P. Spanish Patent No. ES 551830, 1986.
4. Llobet, P. P.; Baylina, G. E. Spanish Patent No. ES 2006167, 1989.
5. For some recent solid-phase syntheses of benzimidazoles, see: Wu C.-Y., Sun C.-M. Tetrahedron Lett. 43:2002;1529-1533. and references cited therein.
6. Bohm, G. G. A.; Graves, D. F. US Patent No. 4788229, 1988.
7. Wu, Z.; Ercole, F.; FitzGerald, M.; Perera, S.; Riley, P.; Campbell, R.; Pham, Y.; Rea, P.; Sandanayake, S.; Mathieu, M. N.; Bray, A. M.; Ede, N. J. J. Comb. Chem., 2003, 5, in press. The key step of the synthesis involves conversion of the arylnitro methyl esters to the tetrahydro-1,4-benzodiazepine-2-ones via a reductive cyclization
8. (a) Finch, H.; Trist, D. G.; Tarzia, G.; Feriani, A. US Patent No. 5580895, 1996; (b) Claremon, D. A.; Liverton, N.; Selnick, H. G. US Patent No. 5700797, 1997; (c) Hagishita, S.; Kamata, S.; Seno, K.; Haga, N.; Ishihara, Y. US Patent No. 5776929, 1998.
9. (a) Finch, H.; Trist, D. G.; Tarzia, G.; Feriani, A. US Patent No. 5580895, 1996; (b) Claremon, D. A.; Liverton, N.; Selnick, H. G. US Patent No. 5700797, 1997; (c) Hagishita, S.; Kamata, S.; Seno, K.; Haga, N.; Ishihara, Y. US Patent No. 5776929, 1998.
10. (a) Finch, H.; Trist, D. G.; Tarzia, G.; Feriani, A. US Patent No. 5580895, 1996; (b) Claremon, D. A.; Liverton, N.; Selnick, H. G. US Patent No. 5700797, 1997; (c) Hagishita, S.; Kamata, S.; Seno, K.; Haga, N.; Ishihara, Y. US Patent No. 5776929, 1998.
11. Wu Z., Ede N.J. Tetrahedron Lett. 42:2001;8115-8118.
12. 3): δ 8.50, (s, 1H), 8.16 (dd, J=1.6 Hz, 8 Hz, 1H), 7.62 (d, J=8 Hz, 1H), 4.32 (q or overlapping t, J=7.6 Hz, 2H), 3.83 (s, 3H), 2.91 (s, 2H), 1.88 (m, 2H), 1.44 (m, 2H), 1.06 (t, J=7.6 Hz, 3H) (minor peaks due to the corresponding benzimidazole are not quoted).
13. 2O for HPLC and LC-MS analysis.