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Synlett 1998; 1998(5): 513-515
DOI: 10.1055/s-1998-1696
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Synthesis of a Tetrahydroquino[2,1-c][1,4]benzodiazepine Ring System via Electrochemically Prepared α-Aminonitriles

Erwan Le Gall* , Tristan Renaud, Jean-Pierre Hurvois, André Tallec, Claude Moinet
  • *Laboratoire d'Electrochimie, Université de Rennes I, Campus de Beaulieu, F-35042 Rennes Cedex, France; Fax 33(0)2 99 28 16 60; E-mail: Jean-Pierre.Hurvois@univ-rennes.fr
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Publication Date:
31 December 2000 (online)

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The synthesis of the 7-amino-5,6,6a,13-tetrahydroquino[2,1-c][1,4]benzodiazepine 7 starting from the readily available 1-(2-nitrobenzyl)-1,2,3,4-tetrahydroquinoline 1 is described. The two key steps are an electrochemical cyanation and a deprotection-cyclization between an amino group and the cyano substituent.

[1,4]benzodiazepine - amidine containing heterocycle - α-aminonitrile - t-butoxycarbonylation - electrochemistry