Novel 3-aza-Grob fragmentation in hydride reduction of ether-protected aromatic lactams

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5725-5727

  Wang, Jeh Jeng ^a   Hu, Wan Ping ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; LACTAM DERIVATIVE; N METHOXYMETHYLPYRROLO[2,1 C][1,4]BENZODIAZEPINE 5,11 DIONE; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER INHIBITION; CHEMICAL REACTION KINETICS; DNA ALKYLATION; NITROGEN METABOLISM; ORGANIC CHEMISTRY; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS;

EID: 0033597838     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990549k     Document Type: Article

References (14)

1. Weyersthal, P.; Marschall, H. Fragmentation Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 6, p 1044.
2. Grob, C. A.; Schiess, P. W. Angew. Chem., Int. Ed. Engl. 1967, 6, 1.
3. Grob, C. A. Angew. Chem., Int. Ed. Engl. 1969, 8, 535.
4. Becker, K. B.; Grob, C. A. In The Chemistry of Double-bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Part 2, p 653.
5. Thurston, D. E. Advances in the Study of Pyrrolo[2,1-c][1,4]-benzodiazepine (PBD) Antitumor Antibiotics. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S., Waring, M. J., Eds.; Macmillan Press: New York, 1993; Vol. 1, pp 54-88.
6. Thurston, D. E.; Bose, D. S. Chem. Rev. 1994, 94, 433.
7. Wang, J. J.; Hu, W. P.; Chung, H. W.; Wang, L. F.; Hsu, M. H. Tetrahedron 1998, 54, 13149-13164.
8. Thurston, D. E.; Kaumaya, P. T. P.; Hurley, L. H. Tetrahedron Lett. 1984, 25, 2649 and references therein.
9. Wharton, P. S. J. Org. Chem. 1961, 26, 4781.
10. Wharton, P. S.; Hiegel, G. A.; Coombs, R. V. J. Org. Chem. 1983, 28, 3217.
11. Wharton, P. S.; Hiegel, G. A. J. Org. Chem. 1966, 30, 3254.
12. Caine, D. Org. Prep. Proced. Int. 1988, 20, 1.
13. Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis, 2nd ed.; John Wiley & Sons: New York, 1991.
14. Connor, D. S.; Klein, G. W.; Taylor, G. N.; Boeckman, R. K., Jr.; Medwid, J. B. Organic Synthesis; Wiley: New York, 1986; Collect. Vol. VI, p 101.