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Über die Synthese von Dihydro-1,2,3,5-thiatriazol-1,1-dioxiden, 1. Mitt.

Synthesis of dihydro-1,2,3,5-thiatriazole-1,1-dioxides, I

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

2,5-Dihydro-1,2,3,5-thiatriazole-1,1-dioxides2 a–2 c were obtained on treating N1-acyl-sulfamoylhydrazides with PCl5, yielding the corresponding N2-sulfamoyl-carbohydrazonoylchlorides which cyclized after addition of KOH orn-butyllithium.

Methylation of2 c yields2 b and the 2,3-isomer10 in a 1 : 1 ratio.

Reaction of the nitrilimine11 with the N-sulfonylamine12 affords the tetrazine13 and the isomeric dihydrothiatriazole-1,1-dioxides14 and15 via 1,3-dipolar cycloaddition reaction, while the dihydro-1,2,3,5-thiatriazole-1,1-dioxid16 reacts with ethyl chloroformate to yield the isomers14 and17.

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Authors and Affiliations

  1. Institut für Organische Chemie, Technische Universität Wien, A-1060, Wien, Österreich

    Max Knollmüller & Paul Kosma

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  1. Max Knollmüller
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  2. Paul Kosma
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Herrn Prof. Dr. Dr. h.c.K. Kratzl mit den besten Wünschen zum 70. Geburtstag gewidmet.

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Knollmüller, M., Kosma, P. Über die Synthese von Dihydro-1,2,3,5-thiatriazol-1,1-dioxiden, 1. Mitt.. Monatsh Chem 116, 1141–1151 (1985). https://doi.org/10.1007/BF00811248

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  • DOI: https://doi.org/10.1007/BF00811248

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