PDF herunterladen
Synthesis 1992; 1992(9): 879-883
DOI: 10.1055/s-1992-26251
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthese von Imidazo- und Diimidazo[1,2,4,5]tetrazinen; zur Tautomerie von Dihydro-1,2,4,5-tetrazinen

Heinrich Wamhoff* , Harald W. Strobl, Martin Jansen, Martina Ralle
  • *Institut für Organische Chemie und Biochemie der Universität Bonn; Gerhard-Domagk-Str. 1, D-5300 Bonn 1, Germany
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
17. September 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Synthesis of Imidazo- and Diimidazo[1,2,4,5]tetrazines; For Tautomerism of Dihydro-1,2,4,5-tetrazines Dimethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate (1) reacts with isocyanates to afford the 2,7-disubstituted 1H6H -diimidazo[1,5-b: 1′,5′-e] [1,2,4,5]tetrazine-1,3,6,8(2H,7H)-tetrones 2a-m, a hitherto unknown ring system. The linear annulation of 2m was established by X-ray analysis, and as a consequence the 1,4-dihydro tautomer found to be the main constituent of all other potential isomers. Compound 1 reacts with isothiocyanates to give the corresponding 1,6-dithioxo derivatives 5a,b as well as the 7-substituted methyl 2,6,7,8-tetrahydro-8-oxo-6-thioxoimidazo[1,5-b] [1,2,4,5]tetrazine-3-carboxylates 6b,c respectively, while the unsymmetrically substituted 2-tert-butyl-7-(4-chlorophenyl)-6-thioxo-1H, 6H-diimidazo[1,5-b: 1′,5′-e] [1,2,4,5]tetrazine-1,2,8-(2H,7H)-trione (8) is obtained from 6c and the corresponding isocyanate.

      >