Synthesis of a tetrahydroquino[2,1-c][1,4]benzodiazepine ring system via electrochemically prepared α-aminonitriles

Synlett

Volumn , Issue 5, 1998, Pages 513-515

  Le Gall, Erwan ^a   Renaud, Tristan ^a   Hurvois, Jean Pierre ^a   Tallec, André ^a   Moinet, Claude ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

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Indexed keywords

EID: 0005940613     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1696     Document Type: Article

References (21)

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2. S. Michel, E. Le Gall, J. P. Hurvois, C. Moinet, A. Tallec, P. Uriac, L. Toupet, Liebigs Ann J Recueil 1997, 259-267.
3. (a) Anodic oxidation pathway of unsymmetrical tertiary amines. (Chemical Equation Presented)
4. rd ed. (Eds.: H. Lund, M.M. Baizer), Dekker, New York, 1991, 581-594.
5. M. B. Sassaman, Tetrahedron, 1996, 52, 10835-10840.
6. J. Y. David, J. P. Hurvois, A. Tallec, L. Toupet, Tetrahedron 1995, 51, 3181-3196.
7. T. H. Barrows, P. R. Farina, R. L. Chrzanowski, P. A. Benkovic, S. J. Benkovic, J. Am. Chem. Soc. 98, 1976, 3678-3689.
8. W. Metlesics, G. Silverman, L. H. Sternbach, J. Org. Chem. 1963, 28, 2459-2460.
9. W. B. Wright, E. N. Greenblatt, I. P. Day, N. Q. Quinones, R. A. Hardy, J. Med. Chem. 1980, 23, 462-465.
10. For the reduction of nitro groups into the corresponding amines see: M. Hudlicky in Reductions in Organic Chemistry, Chichester, 1984, Ellis Horwood Limited.
11. N. L. Weinberg, H. R. Weinberg, Chem Review 1968, 68, 449-523.
12. E. Le Gall, J. P. Hurvois 1995, unpublished results.
13. Coulometric datas performed at controlled potential (+ 0.75 V/ SCE) and recorded at a planar carbon electrode shown a consumption of 4 and 2 moles of electron per mole of substrate for compounds 4 and 5 respectively and confirm the hypothesis that both the primary and the tertiary amino group of 4 were oxidized at the same potential.
14. E. Ponnusamy, U. Fotadar, A. Spisni, D. Fiat, Synthesis 1986, 48-49.
15. We suggest that a Retro-Strecker reaction may be responsible for the lack of compond cyanated at the benzylic position.
16. E Kaiser, J. P. Tarn, T. M. Kubiak, R. B. Merrifield, Tetrahedron Lett. 1988, 29, 306-308.
17. V. Boyd in The chemistry of amidines and imidates, vol. 2, (Ed. : S. Patai and Z. Rappoport), John Wiley and Sons, New York, 1991.
18. 2 / MeOH: 90 / 10).
19. 2 : calcd. C 72.70, H 6.93, N 11.56, O 8.80 ; found C 72.50, H 7.14, N 11.52, O 8.73.
20. f = 0.50 (dichloromethane/methanol, 80:20).
21. 2) calculated according to a bielectronic process is given by the expression: i (ampere) = 2 X f X 96500 X 10-3 M/60. (Figure Presented)