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

József Reiter, József Barkóczy, G. Argay, A. Kálmán

Research output: Contribution to journalArticle

4 Citations (Scopus)

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
Publication statusPublished - 2000

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Thiadiazoles
Triazoles
Morpholinos
Bond length
X ray diffraction analysis
Derivatives
Oxidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

On triazoles XLI [1]. Synthesis of meso-ionic [1,2,4]triazolo[5,1- c]thiadiazoles. / Reiter, József; Barkóczy, József; Argay, G.; Kálmán, A.

In: Journal of Heterocyclic Chemistry, Vol. 37, No. 2, 2000, p. 261-267.

Research output: Contribution to journalArticle

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AU - Kálmán, A.

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N2 - 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.

AB - 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.

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