Über die Synthese von Dihydro-1,2,3,5-thiatriazol-1,1-dioxiden, 1. Mitt. |
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| Authors: | Max Knollmüller Paul Kosma |
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| Affiliation: | (1) Institut für Organische Chemie, Technische Universität Wien, A-1060 Wien, Österreich |
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| 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.Herrn Prof. Dr. Dr. h.c.K. Kratzl mit den besten Wünschen zum 70. Geburtstag gewidmet. |
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| Keywords: | N-Phenyl-benzenecarbohydrazonoylchloride Cycloaddition reaction with N-[[(Ethoxycarbonyl)amino]sulfonyl]-N,N-diethylethanaminium, hydroxide, inner salt |
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