4.5 Article

Unusual Expansion of the 1,2,4,5-Tetrazine Ring in [1,2,4]Triazolo[4,3-b]-[1,2,4,5]tetrazines Leading to [1,2,4,6]Tetrazepine Systems

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 12, Pages 2309-2318

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001590

Keywords

Nitrogen heterocycles; Ring expansion; C-H activation; Nucleophilic substitution

Funding

  1. Russian Academy of Sciences [09-I-3-2004, 09-P-3-2001, 09-T-3-1016]
  2. Russian Foundation for Basic Research [11-03-00545-a]
  3. State Contract [02.740.11.0260]
  4. State Program for Supporting of Leading Scientific Schools of Russian Federation [NSh-65261.2010.3]

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Expansion of the tetrazine ring has first been found to occur when [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines were allowed to react with CH-active compounds in acetonitrile in the presence of triethylamine to give the unexpected series of 8,9-dihydro-7H-[1,2,4]-triazolo[4,3-b][1,2,4,6] tetrazepine derivatives.

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