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Synthesis 1987; 1987(11): 986-989
DOI: 10.1055/s-1987-28143
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Efficient Synthesis of 5,5-Dialkyl-Δ1-1,2,4-triazolin-3-ones by Acid Hydrolysis of Bis(α-isocyanatoalkyl)diazenes

Joachim G. Schantl* , Hubert Gstach, Norbert Lanznaster
  • *Institut für Organische und Pharmazeutische Chemie der Universität Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria
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Publication Date:
12 September 2002 (online)

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The hydrolysis of bis(α-isocyanatoalkyl)diazenes with hydrochloric acid affords the novel 5,5-dialkyl-Δ1-1,2,4-triazolin-3-ones in good yields, and is a minor by-product, the corresponding 4-aminocarbonyl derivatives. The 1,2,4-triazolin-3-ones are easily converted into the 4-benzoyl derivatives which, in turn, react as mild benzoylating agents toward primary amines.