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Original scientific paper

The Mannich Reaction for 2,5-Dimercapto-1,3,4-thiadiazole

J. Kobe ; Department of Chemistry, University of Ljubljana, Ljubljana, Slovenia, Yugoslavia
A. Pollak ; Department of Chemistry, University of Ljubljana, Ljubljana, Slovenia, Yugoslavia
B. Stanovnik ; Department of Chemistry, University of Ljubljana, Ljubljana, Slovenia, Yugoslavia
M. Tišler ; Department of Chemistry, University of Ljubljana, Ljubljana, Slovenia, Yugoslavia


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Abstract

The formation of Mannich bases with 2,5-dimercapto-1,3,4-
-thiadiazole (III) and some of its derivatives has been investigated.
Depending on the amount of formaldehyde and a secondary amine
used in the reaction, three different types of Mannich bases were
prepared. With equimolecular amounts of both reagents a mono-
Mannich base IV was obtained, but using formaldehyde in excess
a mono-hydroxymethyl mono-M.annich base V was isolated. If both
reagents were used in amounts corresponding to two equivalents, a
bis-Mannich base VI was formed. Evidence- for the structures of all
these products was presented on the basis of chemical transformatfons
and spectroscopic data. The mono-Mannich base IV .was
converted in its S-methyl derivative VIII which was prepared
independently from IX in a Mannich reaction. Thus aminoalkylation
proceeds first on the ring nitrogen and in a further reaction the
exo-cyclic sulfur is substituted.

Keywords

Hrčak ID:

208190

URI

https://hrcak.srce.hr/208190

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