A remarkable two-step synthesis of diverse 1,4-benzodiazepine-2,5-diones using the Ugi four-component condensation

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8935-8939

  Keating, Thomas A ^a   Armstrong, Robert W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZODIAZEPINE 2,5 DIONE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030443529     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961517p     Document Type: Article

References (25)

1. McDowell, R. S.; Blackburn, B. K; Gadek, T. R.; McGee, L. R.; Rawson, T.; Reynolds, M. E.; Robarge, K. D.; Somers, T. C.; Thorsett, E. D.; Tischler, M.; Webb, R. R., II; Venuti, M. C. J. Am. Chem. Soc. 1994, 116, 5077.
2. Cho, N. S.; Song, K. Y.; Párkányi, C. J. Heterocycl. Chem. 1989, 26, 1807-1810.
3. Bauer, A.; Weber, K.-H.; Danneberg, P.; Kuhn, F.-J. U.S. Patent 3 914 216, 1975.
4. Martino, G. D.; Massa, S.; Corelli, F.; Pantaleoni, G.; Fanini, D.; Palumbo, G. Eur. J. Med. Chem.-Chim. Ther. 1983, 18, 347.
5. Ananthan, S.; Clayton, S. D.; Ealick, S. E.; Wong, G.; Evoniuk, G. E.; Skolnick, P. J. Med. Chem. 1993, 36, 479-490.
6. Wong, G.; Koehler, K. F.; Skolnick, P.; Gu, Z.-Q.; Ananthan, S.; Schönholzer, P.; Hunkeler, W.; Zhang, W.; Cook, J. M. J. Med. Chem. 1993, 36, 1820-1830.
7. Wright, W. B., Jr.; Brabander, H. J.; Greenblatt, E. N.; Day, I. P.; Hardy, R. A., Jr. J. Med. Chem. 1978, 21, 1087.
8. Jones, G. B.; Davey, C. L.; Jenkins, T. C.; Kamal, A.; Kneale, G. G.; Neidle, S.; Webster, G. D.; Thurston, D. E. Anti-Cancer Drug Des. 1990, 5, 249.
9. Moroder, L.; Lutz, J.; Grams, F.; Rudolph-Böhner, S.; Ösapay, G.; Goodman, M.; Kolbeck, W. Biopolymers 1996, 38, 295-300 and extensive references contained therein.
10. Kim, D. H. J. Heterocycl. Chem. 1975, 12, 1323-1324.
11. Karp, G. M. J. Org. Chem. 1995, 60, 5814-5819.
12. Boojamra, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742-5743.
13. Goff, D. A.; Zuckermann, R. N. J. Org. Chem. 1995, 60, 5744-5745.
14. Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006.
15. Gokel, G.; Lüdke, G.; Ugi, I. In Isonitrile Chemistry; Ugi, I., Ed.; Academic: New York, 1971; pp 145-199.
16. (a) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123-131.
17. (b) Armstrong, R. W.; Brown, S. D.; Keating, T. A.; Tempest, P. A. In Combinatorial Chemistry: Synthesis and Application; Wilson, S. R., Czarnik, A. W., Eds.; Wiley-Interscience: New York, in press.
18. Rosendahl, F. K.; Ugi, I. Ann. Chem. 1963, 666, 65-67.
19. Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 7842-7843.
20. Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583.
21. Potts, K. T. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 2, pp 1-82.
22. Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F. C. Angew. Chem., Int. Ed. Engl. 1964, 3, 136-137.
23. Akssira, M.; Boumzebra, M.; Kasmi, H.; Dahdouh, A.; Roumestant, M. L.; Viallefont, P. Synth. Commun. 1993, 23, 2265-2272.
24. Barton, D. H. R.; Bowles, T.; Huisnec, S.; Forbes, J. E.; Llobera, A.; Porter, A. E. A.; Zard, S. Z. Tetrahedron Lett. 1988, 29, 3343-3346.
25. Baldwin, J. E.; Yamaguchi, Y. Tetrahedron Lett. 1989, 30, 3335-3338.