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Synthesis 2007(24): 3791-3796
DOI: 10.1055/s-2007-990893
DOI: 10.1055/s-2007-990893
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Reactivity of 2,3-Dihydro-1H-2,3-benzodiazepine-1,4(5H)-dione
Further Information
Received
14 May 2007
Publication Date:
15 November 2007 (online)
Publication History
Publication Date:
15 November 2007 (online)
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
- 1
Bourguignon JJ.Oumouch S.Schmitt M. Curr. Org. Chem. 2006, 10: 277 -
2a
Watterson DM.Mirzoeva S.Guo L.Whyte A.Bourguignon JJ.Hilbert M.Haiech J.Van Eldik LJ. Neurochem. Int. 2001, 39: 459 -
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 -
2c
Contreras JM.Rival YM.Chayer S.Bourguignon JJ.Wermuth CG. J. Med. Chem. 1999, 42: 730 -
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 - 3
Whitmore WF.Cooney RC. J. Am. Chem. Soc. 1944, 66: 1237 -
4a
Rosen G.Popp FD. J. Heterocycl. Chem. 1969, 6: 9 -
4b
Flammang M. Ph.D. Thesis Louis Pasteur University; Strasbourg (France): 1974. - 5
Loser R.Schilling K.Dimmig E.Gutschow M. J. Med. Chem. 2005, 48: 7688 - 6
Sabitha G.Srividya R.Yadav JS. Tetrahedron 1999, 55: 4015 -
7a
Keck GE.Boden E.Sonnewald U. Tetrahedron Lett. 1981, 22: 2615 -
7b
Zhang HJ.Padwa A. Org. Lett. 2006, 8: 247 - 8
Fukuyama T.Cheung M.Jow CK.Hidai Y.Kan T. Tetrahedron Lett. 1997, 38: 5831 -
9a
Raboisson P.Baurand A.Cazenave JP.Gachet C.Schultz D.Spiess B.Bourguignon JJ. J. Org. Chem. 2002, 67: 8063 -
9b
McCluskey A.Keller PA.Morgan J.Garner J. Org. Biomol. Chem. 2003, 1: 3353 -
9c
Kuhnert N.Clemens I.Walsh R. Org. Biomol. Chem. 2005, 3: 1694 - 10
Bischofberger N. Tetrahedron Lett. 1987, 28: 2821 - 11
Hellal M.Bihel F.Mongeot A.Bourguignon JJ. Org. Biomol. Chem. 2006, 4: 3142 - 12
Kissounko DA.Guzei IA.Gellman SH.Stahl SS. Organometallics 2005, 24: 520 - 13
Spangler RJ.Kim JH.Cava MP. J. Org. Chem. 1977, 42: 1697