Ring formation from 2-arylazo-3-aminocrotononitriles to 1,2,3[2H]-triazole-4-carbonitriles and pyrazoles by anodic oxidation

Electrochimica Acta

Volumn 42, Issue 1, 1997, Pages 73-79

  Weit, Xudong ^a   Speiser, Bernd ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Anodic oxidation; Electrochemistry; Enamines; Heterocyclic ring formation; Pyrazoles; Triazoles

Indexed keywords

ACETONITRILE; ANODIC OXIDATION; ELECTROCHEMISTRY; METHANOL; REACTION KINETICS;

ENAMINES; HETEROCYCLIC RING FORMATIONS; POTENTIOSTATIC REACTION CONDITIONS; PYRAZOLES; RING FORMATION; TRIAZOLES;

AMINES;

EID: 0030836847     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/0013-4686(96)00168-5     Document Type: Article

References (26)

1. B. Hirsch, D. Lohmann and G. Faust, Patent DD 209 820, VEB Arzneimittelwerk, Dresden (1984).
2. H. Wamhoff, in Comprehensive Heterocyclic Chemistry (Edited by A. R. Katritzky, C. W. Rees and K. T. Potts), Vol. 5, pp. 669-732. Pergamon, Oxford (1984).
3. A. F. Strobel and M. L. Whitehouse, Patent Ger. Offen. 2,129,683, GAF Corp., December (1971); Chem. Abstr. 76, 128832j (1972).
4. A. F. Strobel and M. L. Whitehouse, Patent Ger. Offen. 2,129,864, GAF Corp., December (1971); Chem. Abstr. 76, 99674b (1972).
5. B. Hirsch, D. Lohmann, G. Menzel, G. Schuster and E. Stenz, Patent DD 234 004 A1, VEB Arzneimittelwerk, Dresden (1986).
6. B. Hirsch, D. Lohmann and G. Faust, Patent DD 209 819, VEB Arzneimittelwerk, Dresden (1984).
7. M. Begtrup, J. Chem. Soc., Perkin Trans, 1, 2749 (1982).
8. T. Shono in The Chemistry of Enamines, Part I (Edited by Z. Rappoport) Chapter 8, pp. 459-465. Wiley, Chichester (1994).
9. M. Masui, T. Michida, C. Ueda and H. Ohmori, Chem. Ind. 922 (1978).
10. M. Cariou, R. Carlier and J. Simonet, J. Chem. Soc., Chem. Commun. 876 (1983).
11. M. Cariou, R. Carlier and J. Simonet, Bull. Soc. Chim. France 781 (1986).
12. T. Shono, Y. Matsumura, J. Hayashi, M. Usui, S.-I. Yamane and K. Inoue, Acta Chem. Scand. B37, 491 (1983).
13. D. Koch and H. Schäfer, Angew. Chem. 85, 264 (1973); Angew. Chem. Im. Ed. Engl, 12, 254 (1973).
14. D. Koch and H. Schäfer, Angew. Chem. 85, 264 (1973); Angew. Chem. Im. Ed. Engl, 12, 254 (1973).
15. W. Eilenberg and H. J. Schäfer, Tetrahedron Lett. 25, 5023 (1984).
16. I. Tabaković, Electrochim. Acta 40, 2809 (1995).
17. K. Hu, M. E. Niyazimbetov and D. H. Evans, J. Electroanal. Chem. 396, 457 (1995).
18. T. Shono, Y. Matsumura, H. Hamaguchi, T. Imanishi and K. Yoshida, Bull. Chem. Soc. Jpn. 51, 2179 (1978).
19. T. Chiba, M. Okimoto, H. Nagai and Y. Takata, J. Org. Chem. 44, 3519 (1979).
20. X. Wei and B. Speiser, Electrochim. Acta 40, 2477 (1995).
21. J. Elguero in Comprehensive Heterocyclic Chemistry (Edited by A. R. Katritzky, C. W. Rees and K. T. Potts), Vol. 5, pp. 169-305. Pergamon, Oxford (1984).
22. G. Gritzner and J. Kůta, Pure Appl. Chem. 56, 461 (1984).
23. B. Hirsch, Liebigs Ann. Chem. 690, 33 (1965).
24. A. O. Abdehamid, C. Párkányi, A. S. Shawali and M. A. Abdalla, J. Heterocycl. Chem. 21, 1049 (1984).
25. W. W. Schoeller, J. Niemann and P. Rademacher, J. Chem. Soc., Perkin II, 369 (1988).
26. P. Audebert, H. Bekolo, J. Cossy and A. Bouzide, J. Electroanal. Chem. 389, 215 (1995).