Ring Transformations of Semicyclic 1,3-Dicarbonyl Heteroanalogs; IV1. Synthesis of 3-(ω-Aminoalkyl)-1,2,4-thiadiazoles by Ring Transformation Reaction of Semicyclic Thioacylamidines with 3,3-Pentamethyleneoxaziridine

Michael Pätzel; Jürgen Liebscher; Siegfried Andreae; Ernst Schmitz

doi:10.1055/s-1990-27097

Synthesis 1990; 1990(11): 1071-1073
DOI: 10.1055/s-1990-27097

paper

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Ring Transformations of Semicyclic 1,3-Dicarbonyl Heteroanalogs; IV¹. Synthesis of 3-(ω-Aminoalkyl)-1,2,4-thiadiazoles by Ring Transformation Reaction of Semicyclic Thioacylamidines with 3,3-Pentamethyleneoxaziridine

Michael Pätzel^* , Jürgen Liebscher, Siegfried Andreae, Ernst Schmitz

^*Humboldt-Universität Berlin, Fachbereich Chemie, Hessische Str. 1-2, O-1040 Berlin, Germany

Abstract

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Semicyclic thioacylamidines 1 react with 3,3-pentamethyleneoxaziridine by ring transformation affording novel ω-aminoalkyl-1,2,4-thiadiazoles 5, which are conveniently isolated as hydrochlorides 6. These can be transformed to the corresponding free bases 5, which in one case are methylated at the amino group to give an ω-dimethylaminoalkyl-1,2,4-thiadiazole 7.

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