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

doi:10.1055/s-1987-28143

Synthesis 1987; 1987(11): 986-989
DOI: 10.1055/s-1987-28143

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.

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

Abstract

PDF Download All articles of this category

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.

PDF (368 kb)