Synthesis and Reactivity of 2,3-Dihydro-1H-2,3-benzodiazepine-1,4(5H)-dione

Frédéric J.-J. Bihel; Malik Hellal; Jean-Jacques Bourguignon

doi:10.1055/s-2007-990893

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Synthesis 2007(24): 3791-3796
DOI: 10.1055/s-2007-990893

PAPER

Synthesis and Reactivity of 2,3-Dihydro-1H-2,3-benzodiazepine-1,4(5H)-dione

Frédéric J.-J. Bihel*, Malik Hellal, Jean-Jacques Bourguignon
Institut Gilbert Laustriat, UMR 7175 CNRS, Département Pharmacochimie de la Communication Cellulaire, Faculté de pharmacie, Université Strasbourg I, 74 route du rhin, BP60024, 67400 Illkirch Graffenstaden, France
Fax: +33(3)90244310; e-Mail: frederic.bihel@pharma.u-strasbg.fr;

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Publication History

Received 14 May 2007
Publication Date:
15 November 2007 (online)

Abstract
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Abstract

Based on an orthogonal protective group strategy dealing with N-protected hydrazine, we established for the first time a highly efficient synthetic pathway leading to 2,3-benzodiazepine-1,4-dione. Moreover, the versatile reactivities exhibited by this 2,3-benzodiazepine-1,4-dione were evaluated towards both benzylation and amination reactions.

Key words

benzodiazepine - hydrazine - amides - aminations - bicyclic compounds

References

1 Bourguignon JJ. Oumouch S. Schmitt M. Curr. Org. Chem. 2006, 10: 277

Crossref Google Scholar
2a Watterson DM. Mirzoeva S. Guo L. Whyte A. Bourguignon JJ. Hilbert M. Haiech J. Van Eldik LJ. Neurochem. Int. 2001, 39: 459

Crossref Google Scholar
2b Mirzoeva S. Sawkar A. Zasadzki M. Guo L. Velentza AV. Dunlap V. Bourguignon JJ. Ramstrom H. Haiech J. Van Eldik LJ. Watterson DM. J. Med. Chem. 2002, 45: 563

Crossref Google Scholar
2c Contreras JM. Rival YM. Chayer S. Bourguignon JJ. Wermuth CG. J. Med. Chem. 1999, 42: 730

Crossref Google Scholar
2d Cesari C. Biancalani N. Vergelli C. Dal Piaz V. Graziano A. Biagini P. Ghelardini C. Galeotti N. Giovannoni MP. J. Med. Chem. 2006, 49: 7826

Crossref Google Scholar
3 Whitmore WF. Cooney RC. J. Am. Chem. Soc. 1944, 66: 1237

Crossref Google Scholar
4a Rosen G. Popp FD. J. Heterocycl. Chem. 1969, 6: 9

Crossref Google Scholar
4b Flammang M. Ph.D. Thesis Louis Pasteur University; Strasbourg (France): 1974.

Crossref Google Scholar
5 Loser R. Schilling K. Dimmig E. Gutschow M. J. Med. Chem. 2005, 48: 7688

Crossref Google Scholar
6 Sabitha G. Srividya R. Yadav JS. Tetrahedron 1999, 55: 4015

Crossref Google Scholar
7a Keck GE. Boden E. Sonnewald U. Tetrahedron Lett. 1981, 22: 2615

Crossref Google Scholar
7b Zhang HJ. Padwa A. Org. Lett. 2006, 8: 247

Crossref Google Scholar
8 Fukuyama T. Cheung M. Jow CK. Hidai Y. Kan T. Tetrahedron Lett. 1997, 38: 5831

Crossref Google Scholar
9a Raboisson P. Baurand A. Cazenave JP. Gachet C. Schultz D. Spiess B. Bourguignon JJ. J. Org. Chem. 2002, 67: 8063

Crossref Google Scholar
9b McCluskey A. Keller PA. Morgan J. Garner J. Org. Biomol. Chem. 2003, 1: 3353

Crossref Google Scholar
9c Kuhnert N. Clemens I. Walsh R. Org. Biomol. Chem. 2005, 3: 1694

Crossref Google Scholar
10 Bischofberger N. Tetrahedron Lett. 1987, 28: 2821

Crossref Google Scholar
11 Hellal M. Bihel F. Mongeot A. Bourguignon JJ. Org. Biomol. Chem. 2006, 4: 3142

Crossref Google Scholar
12 Kissounko DA. Guzei IA. Gellman SH. Stahl SS. Organometallics 2005, 24: 520

Google Scholar
13 Spangler RJ. Kim JH. Cava MP. J. Org. Chem. 1977, 42: 1697

Crossref Google Scholar