MCC/SNAr methodology. Part 2: Novel three-step solution phase access to libraries of benzodiazepines

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1947-1950

  Tempest, Paul ^a   Pettus, Liping ^a   Gore, Vijay ^a   Hulme, Christopher ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ARGON; BENZODIAZEPINE DERIVATIVE; FUEL; LEAD;

ANALYTIC METHOD; ARTICLE; AUTOMATION; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CYCLIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; POLYMERIZATION; PURIFICATION; SOLID; TECHNOLOGY;

EID: 0037463502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00084-4     Document Type: Article

References (30)

1. For two reviews, see: (a) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 3, 366; (b) Domling, A. Combinatorial Chemistry & High Throughput Screening 1998, 1, 1.
2. For two reviews, see: (a) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 3, 366; (b) Domling, A. Combinatorial Chemistry & High Throughput Screening 1998, 1, 1.
3. Ugi I. Angew. Chem., Int. Ed. Engl. 1:1962;8.
4. Ugi I., Steinbruckner C. Chem. Ber. 94:1961;734.
5. Ugi I., Domling A., Horl W. Endeavor. 18:1994;115.
6. Bienayme H., Hulme C., Oddon G., Schmitt P. Chem. Eur. J. 6:2000;3321.
7. Passerini M. Gazz. Chim. Ital. 51:1921;126.
8. Gokel G., Ludke G., Ugi I. Ugi I. Isonitrile Chemistry. 1971;145 Academic Press, New York.
9. Semple J.E., Owens T.D., Nguyen K., Levy O.E. Org. Lett. 2:2000;2769.
10. Semple J.E., Rowley D.C., Brunck T.K., Ripka W.C. Bioorg. Med. Chem. Lett. 7:1997;315.
11. Banfi L., Guanti G., Riva R. Chem. Commun. 2000;985
12. Jones, W.; Tadesse, S.; Chenera, B.; Viswanadhan, V.; Hulme, C. A. C. S. 223rd, American Chemical Society Meeting & Exposition, April 2002, New Orleans.
13. Nixey T., Hulme C. Tetrahedron Lett. 43:2002;6833.
14. Hulme C., Ma L., Romano J., Morrissette M. Tetrahedron Lett. 40:1999;7925.
15. Nixey T., Kelly M., Semin D., Hulme C. Tetrahedron Lett. 43:2002;3681.
16. Hulme C., Ma L., Romano J., Morton G., Tang S.-Y., Cherrier M.-P., Choi S., Labaudiniere R. Tetrahedron Lett. 41:2000;1883.
17. Morales G.A., Corbett J.W., Degrado W.F. J. Org. Chem. 63:1998;1172.
18. Phillips G.B., Wei G.-P. Tetrahedron Lett. 37:1996;4887.
19. Tumelty D., Schwarz M.K., Cao K., Needels M.C. Tetrahedron Lett. 40:1999;6185.
20. Stephensen H., Zaragoza F. Tetrahedron Lett. 40:1999;5799.
21. Lee J., Gauthier D., Rivero R.A. J. Org. Chem. 64:1999;3060.
22. Schwarz M.K., Tumelty D., Gallop M.A. J. Org. Chem. 64:1999;2219.
23. Kiselyov A.S., Smith L., Tempest P. Tetrahedron. 55:1999;14813.
24. Tempest P., Ma V., Kelly M., Jones W., Hulme C. Tetrahedron Lett. 42:2001;4959.
25. Cristau P., Vors J.-P., Zhu J. Org. Lett. 3:2001;4079.
26. Purchased from Argonaut® technologies.
27. For a review of UDC methodology, see: Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
28. 3CN to 100% over 15 min. HPLC was interfaced with APCI techniques.
29. For full experimental details of MCR production protocols, see: Hulme, C.; Bienayme, H.; Nixey, T.; Chenera, B.; Jones, W. J.; Tempest, P.; Smith, A. Library Generation via Post Condensation Modifications of Isocyanide Based Multi-Component Reactions, Methods Enzymol. 2003, in press.
30. 4: M=458, found: (M+1)+=459.