On triazoles XLI [1]. Synthesis of meso-ionic [1,2,4]triazolo[5,1- c]thiadiazoles

József Reiter, József Barkóczy, Gyula Argay, Alajos Kálmán

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Abstract

Type 6 meso-ionic [1,2,4]triazolo[5,1-c]thiadiazoles were synthesised by oxidation of the corresponding N-methyl-N'-(substitutedbenzal)-5-amino-3- substituted-1,2,4-triazol-1-yl)thiohydrazide (3) type bases or their [1,2,4]triazolo[5,1-d][1,2,3,6]tetrazepin-5-thion (4) type ring tautomers. Besides spectroscopical evidence a preparative proof of their structure was also provided. X-ray diffraction analysis of 3-methylthio-6-morpholino-1,2,4- triazolo[5,1-c]thiadiazole (8) showed quite unusual bond lengths for the N1- S and S-C3 bonds of the thiadiazole ring proving the meso-ionic character of these derivatives unequivocally.

Original languageEnglish
Pages (from-to)261-267
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume37
Issue number2
DOIs
Publication statusPublished - Jan 1 2000

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ASJC Scopus subject areas

  • Organic Chemistry

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