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Synlett 1998; 1998(7): 786-788
DOI: 10.1055/s-1998-1759
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Tandem [3 + 2] Cycloaddition Reaction of Azo-alkenes and Thiocyanic Acid: Extending the Scope of the Classical "Criss-Cross" Cycloaddition Reaction

Joachim G. Schantl* , Peter Nádeník
  • *Institut für Organische Chemie, Universität Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria; Fax +43 (0)512 507 2855; E-mail: Joachim.Schantl@uibk.ac.at
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Publication Date:
31 December 2000 (online)

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Phenylazoalkenes 4 with full substitution at the terminal carbon atom react with thiocyanic acid affording 2,3,5,6,7,7a-hexahydro-3-phenyl-1H-imidazo[1,5-b][1,2,4]triazole-2,5-dithiones 8. The bicyclic compounds 8 result from two consecutive [3 + 2] cycloaddition steps, thus adding a novel facet to the classical "Criss-cross" reaction.

azo-alkenes - azomethine imines - cycloadditions - bicyclic heterocyclic compounds

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