A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives

The main purpose of the study was the development of a new method for synthesis of 1,3,4-thiadiazol-2-amine derivatives in a one-pot manner using the reaction between a thiosemicarbazide and carboxylic acid without toxic additives such as POCl3 or SOCl2. The reaction was investigated in the presence...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2021-08, Vol.26 (17), p.5159
Main Authors: Kokovina, Tatiana S., Gadomsky, Svyatoslav Y., Terentiev, Alexei A., Sanina, Nataliya A.
Format: Article
Language:English
Subjects:
1,3,4-thiadiazole-2-amine
Additives
Carboxylic acids
Communication
cyclodehydration reaction
Hydrochloric acid
Mass spectrometry
Mass spectroscopy
NMR
Nuclear magnetic resonance
one-pot synthesis
polyphosphate ester
Thiadiazoles
Thiosemicarbazides
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Summary:The main purpose of the study was the development of a new method for synthesis of 1,3,4-thiadiazol-2-amine derivatives in a one-pot manner using the reaction between a thiosemicarbazide and carboxylic acid without toxic additives such as POCl3 or SOCl2. The reaction was investigated in the presence of polyphosphate ester (PPE). It was found that, in the presence of PPE, the reaction between the thiosemicarbazide and carboxylic acid proceeds in one-pot through three steps with the formation of corresponding 2-amino-1,3,4-thiadiazole. Using the developed approach five, 2-amino-1,3,4-thiadiazoles were synthesized. The structures of all compounds were proven by mass spectrometry, IR, and NMR spectroscopies.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26175159