A new route for the synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via oxidation of cyclic secondary amine

Chemical Communications

Volumn , Issue 3, 1996, Pages 385-386

  Kamal, Ahmed ^a   Venugopal Rao, N ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; BENZODIAZEPINE DERIVATIVE; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030057641     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000385     Document Type: Article

References (23)

1. W. A. Remers, Antitumour Antibiotics, Wiley, 1988, pp. 28-92; D. E. Thurston, Advances in the Study of Pyrrolo[2,1-c][1,4]benzodiazepine (PBD) Antitumour Antibiotics, in Molecular Aspects of Anticancer Drug-DNA Interactions, ed. S. Neidle and M. J. Waring, Macmillan, 1993, vol. 1, pp. 54-88.
2. W. A. Remers, Antitumour Antibiotics, Wiley, 1988, pp. 28-92; D. E. Thurston, Advances in the Study of Pyrrolo[2,1-c][1,4]benzodiazepine (PBD) Antitumour Antibiotics, in Molecular Aspects of Anticancer Drug-DNA Interactions, ed. S. Neidle and M. J. Waring, Macmillan, 1993, vol. 1, pp. 54-88.
3. L. H. Hurley and D. R. Needham-van Devander, Acc. Chem. Res., 1986, 19, 230; L. H. Hurley, J. Med. Chem., 1989, 32, 2027; D. E. Thurston and A. S. Thompson, Chem. Br., 1990, 26, 767.
4. L. H. Hurley and D. R. Needham-van Devander, Acc. Chem. Res., 1986, 19, 230; L. H. Hurley, J. Med. Chem., 1989, 32, 2027; D. E. Thurston and A. S. Thompson, Chem. Br., 1990, 26, 767.
5. L. H. Hurley and D. R. Needham-van Devander, Acc. Chem. Res., 1986, 19, 230; L. H. Hurley, J. Med. Chem., 1989, 32, 2027; D. E. Thurston and A. S. Thompson, Chem. Br., 1990, 26, 767.
6. (a) W. Leimgruber, A. D. Batcho and R. C. Czajkowski, J. Am. Chem. Soc., 1968, 90, 5641;
7. (b) T. Kaneko, H. Wong and T. W. Doyle, Tetrahedron Lett., 1983, 24, 5165;
8. (c) J. W. Suggs, Y. S. Wang and K. S. Lee, Tetrahedron Lett., 1985, 26, 4871.
9. J. W. Lown and A. V. Joshua, Biochem. Pharmacol., 1979, 28, 2017; D. E. Thurston and D. R. Langley, J. Org. Chem., 1986, 51, 705; N. Langlois F. Favre and A. Rojas, Tetrahedron Lett., 1993, 34, 4635.
10. J. W. Lown and A. V. Joshua, Biochem. Pharmacol., 1979, 28, 2017; D. E. Thurston and D. R. Langley, J. Org. Chem., 1986, 51, 705; N. Langlois F. Favre and A. Rojas, Tetrahedron Lett., 1993, 34, 4635.
11. J. W. Lown and A. V. Joshua, Biochem. Pharmacol., 1979, 28, 2017; D. E. Thurston and D. R. Langley, J. Org. Chem., 1986, 51, 705; N. Langlois F. Favre and A. Rojas, Tetrahedron Lett., 1993, 34, 4635.
12. T. Kaneko, H. Wong, T. W. Doyle, W. C. Rose and W. T. Bradner, J. Med. Chem., 1985, 28, 388.
13. D. R. Langley and D. E. Thurston, J. Org. Chem., 1987, 52, 91; S. M. Courtney and D. E. Thurston Tetrahedron Lett., 1993, 34, 5327; D. S. Bose, G. B. Jones and D. E. Thurston, Tetrahedron, 1992, 48, 751.
14. D. R. Langley and D. E. Thurston, J. Org. Chem., 1987, 52, 91; S. M. Courtney and D. E. Thurston Tetrahedron Lett., 1993, 34, 5327; D. S. Bose, G. B. Jones and D. E. Thurston, Tetrahedron, 1992, 48, 751.
15. D. R. Langley and D. E. Thurston, J. Org. Chem., 1987, 52, 91; S. M. Courtney and D. E. Thurston Tetrahedron Lett., 1993, 34, 5327; D. S. Bose, G. B. Jones and D. E. Thurston, Tetrahedron, 1992, 48, 751.
16. M. Mori, M. Kimura, Y. Uozumi and Y. Ban, Tetrahedron Lett., 1985, 26, 5947; M. Mori, Y. Uozumi and Y. Ban, J. Chem. Soc., Chem. Commun., 1986, 841.
17. M. Mori, M. Kimura, Y. Uozumi and Y. Ban, Tetrahedron Lett., 1985, 26, 5947; M. Mori, Y. Uozumi and Y. Ban, J. Chem. Soc., Chem. Commun., 1986, 841.
18. P. Molina, I. Diaz and A. Tarraga, Tetrahedron, 1995, 51, 5617.
19. D. E. Thurston and D. S. Bose, Chem. Rev., 1994, 94, 433.
20. A. J. Mancuso and D. Swern, Synthesis, 1981, 165; T. T. Tidwell, Synthesis, 1990, 857.
21. A. J. Mancuso and D. Swern, Synthesis, 1981, 165; T. T. Tidwell, Synthesis, 1990, 857.
22. Y. Jinbo, H. Kondo, M. Taguchi, F. Sakamoto and G. Tsukamoto, J. Org. Chem., 1994, 59, 6057; L. Gentilucci, Y. Grijzen, L. Thijs and B. Zwanenburg, Tetrahedron Lett., 1995, 36, 4665.
23. Y. Jinbo, H. Kondo, M. Taguchi, F. Sakamoto and G. Tsukamoto, J. Org. Chem., 1994, 59, 6057; L. Gentilucci, Y. Grijzen, L. Thijs and B. Zwanenburg, Tetrahedron Lett., 1995, 36, 4665.