Rapid in-plate generation of benzimidazole libraries and amide formation using EEDQ

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5099-5102

  Thomas, James B ^a   Fall, Michael J ^a   Cooper, Julie B ^a   Burgess, Jason P ^a   Carroll, F Ivy ^a  

^a RTI INTERNATIONAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZIMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; LIBRARY; SCREENING;

EID: 0030745360     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01136-2     Document Type: Article

References (13)

1. Reviews: Baldwin, J.; Henderson, I. Med. Res. Rev. 1996, 16, 391-405; Ellman, J.A.; Thompson, L.A. Chem. Rev. 1996, 96, 555-600; Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 57, 8135-73.
2. Reviews: Baldwin, J.; Henderson, I. Med. Res. Rev. 1996, 16, 391-405; Ellman, J.A.; Thompson, L.A. Chem. Rev. 1996, 96, 555-600; Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 57, 8135-73.
3. Reviews: Baldwin, J.; Henderson, I. Med. Res. Rev. 1996, 16, 391-405; Ellman, J.A.; Thompson, L.A. Chem. Rev. 1996, 96, 555-600; Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 57, 8135-73.
4. Phillips, G.B.; Wei, G.P. Tetrahedron Lett. 1996, 37, 4887-4890.
5. Carroll, F.I.; Coleman, M.C. J. Med. Chem. 1975, 18, 318-320.
6. Belleau, B; Martel, R; Lacasse, M; Menard, Weinberg, N.L.; Perron, Y.G. J. Am. Chem. Soc. 1968, 90, 832.
7. All nitroanilines were prepared by the method of Hunger et al. (Helv. Chim. Acta 1960, 43, 1032) and gave satisfactory spectroscopic data.
8. 1H NMR spectrum was long enough to allow complete proton relaxation and therefore quantitative integration. As a check on the method, the benzimidazole corresponding to etonitazene was isolated by column chromatography in 86% yield and was identical to authentic etonitazene. Also, the material from the reaction between 2A and phenyl acetic acid was isolated in 85% yield and provided satisfactory NMR and elemental analyses.
9. Smith, P.W.; Lai, J.Y.Q.; Whittington, A.R.; Cox, B.; Houston, J.G.; Stylli, C.H.; Banks, M.N., Tiller, P.R. Bioorg. Med. Chem. Lett 1994, 4, 2821-2824.
10. Desai, M.C.; Stramiello, L.M.S. Tetrahedron Lett. 1993, 34, 7685-7688.
11. Kiso, Y; Kai, Y; Yajima, H. Chem. Pharm. Bull. 1973, 21, 2507-2510.
12. Carroll, F.I.; Handy, R.W.; Kepler, J.A.; Gratz, J.A. J. Heterocyclic Chem 1967, 4, 262-267.; Adger, B. M.; Young, R.G. Tetrahedron Lett. 1984, 25, 5219-5222.
13. Carroll, F.I.; Handy, R.W.; Kepler, J.A.; Gratz, J.A. J. Heterocyclic Chem 1967, 4, 262-267.; Adger, B. M.; Young, R.G. Tetrahedron Lett. 1984, 25, 5219-5222.