A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives
1
Institute of Problems of Chemical Physics, The Russian Academy of Sciences, 142432 Chernogolovka, Russia
2
Faculty of Fundamental Physical and Chemical Engineering, Lomonosov Moscow State University, 119991 Moscow, Russia
3
Medicinal Chemistry Science and Education Center, Moscow Region State University, 141014 Mytishchi, Russia
*
Author to whom correspondence should be addressed.
Academic Editor: Mohammad Alam
Molecules 2021, 26(17), 5159; https://doi.org/10.3390/molecules26175159
Received: 3 August 2021
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Revised: 19 August 2021
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Accepted: 24 August 2021
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Published: 25 August 2021
(This article belongs to the Special Issue Recent Advances in the Synthesis and Biological Studies of Five-Membered Azaheterocycle 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 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.
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Keywords:
1,3,4-thiadiazole-2-amine; thiadiazoles; polyphosphate ester; cyclodehydration reaction; one-pot synthesis
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MDPI and ACS Style
Kokovina, T.S.; Gadomsky, S.Y.; Terentiev, A.A.; Sanina, N.A. A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives. Molecules 2021, 26, 5159. https://doi.org/10.3390/molecules26175159
AMA Style
Kokovina TS, Gadomsky SY, Terentiev AA, Sanina NA. A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives. Molecules. 2021; 26(17):5159. https://doi.org/10.3390/molecules26175159
Chicago/Turabian StyleKokovina, Tatiana S., Svyatoslav Y. Gadomsky, Alexei A. Terentiev, and Nataliya A. Sanina. 2021. "A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives" Molecules 26, no. 17: 5159. https://doi.org/10.3390/molecules26175159
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