Improved procedure for the solution phase preparation of 1,4- benzodiazepine-2,5-dione libraries via Armstrong's convertible isonitrile and the Ugi reaction

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 8021-8023

  Hulme, Christopher ^a   Peng, John ^a   Tang, Sheng Yuh ^a   Burns, Christopher J ^a   Morize, Isabelle ^a   Labaudiniere, Richard ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 ETHYL 4 HEXYL 1,4 BENZODIAZEPINE 2,5 DIONE; 3 HEXYL 4 DECYL 1,4 BENZODIAZEPINE 2,5 DIONE; 3 ISOPROPYL 4 (4 METHOXYBENZYL) 1,4 BENZODIAZEPINE 2,5 DIONE; 4 BENZYL 3 (2 PYRIDYL) 1,4 BENZODIAZEPINE 2,5 DIONE; 4 ISOBUTYL 3 (2 PHENYLETHYL) 1,4 BENZODIAZEPINE 2,5 DIONE; BENZODIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

EID: 0032582849     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980622r     Document Type: Article

References (16)

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.; Venuti, M. C. J. Am. Chem. Soc. 1994, 116, 5077-5083.
2. Cho, N. S.; Song, K. Y.; Parkanyi, C. J. Heterocycl. Chem. 1989, 26, 1807.
3. (a) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
4. For earlier syntheses of 1,4-benzodiazepines, see: (b) Gates, M. J. Org. Chem. 1980, 45, 1675. (c) Uskokovic, M.; Iacobelli, J.; Wenner, W. J. Org. Chem. 1962, 27, 3606.
5. For earlier syntheses of 1,4-benzodiazepines, see: (b) Gates, M. J. Org. Chem. 1980, 45, 1675. (c) Uskokovic, M.; Iacobelli, J.; Wenner, W. J. Org. Chem. 1962, 27, 3606.
6. (a) Ugi, I. Angew. Chem., Int. Ed. Engl. 1962, 1, 8.
7. (b) Ugi, I.; Steinbruckner, C. Chem Ber. 1961, 94, 734.
8. (c) Ugi, I.; Domling, A.; Horl, W. Endeavor 1994, 18, 115.
9. (a) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 7842-7843.
10. (b) Rosendahl, F. K; Ugi, I. Ann. Chem. 1963, 666, 65.
11. Keating, T. A.; Armstrong, R. W. J. Org. Chem. 1996, 61, 8935.
12. Hulme, C.; Morrissette, M.; Volz, F.; Burns, C. Tetrahedron Lett. 1998, 39, 1113.
13. 0C.
14. A % yield of Ugi product: N-BOC anthranilic acid, 85%, and anthranilic acid, 15%, with isobutylamine, phenylpropionaldehyde, and cyclohexylisocyanide as supporting reagents.
15. (a) Boojamara, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742.
16. (b) Goff, D. A.; Zuckermann, R. N. J. Org. Chem. 1995, 60, 5744.