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Mendeleev Communications, 2011, Volume 21, Issue 6, Pages 331–333
DOI: https://doi.org/10.1016/j.mencom.2011.11.013
(Mi mendc2962)
 

This article is cited in 21 scientific papers (total in 21 papers)

Synthesis of 5-alkyl-2-amino-1,3,4-thiadiazoles and α,ω-bis(2-amino-1,3,4-thiadiazol-5-yl)alkanes in ionic liquids

M. A. Epishinaa, A. S. Kulikova, N. V. Ignat'evb, M. Schulteb, N. N. Makhovaa

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b Ionic Liquid Research Laboratory, Merck KGaA, Darmstadt, Germany
Abstract: Reaction of thiosemicarbazide with carboxylic acids, including N-substituted amino acids, in ionic liquids with H2SO4 as a catalyst affords 5-R-2-amino-1,3,4-thiadiazoles. On using alkanedicarboxylic acids, α,ω-bis(2-amino-1,3,4,-thiadiazol-5-yl)alkanes were obtained.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (206.8 Kb)


Citation: M. A. Epishina, A. S. Kulikov, N. V. Ignat'ev, M. Schulte, N. N. Makhova, “Synthesis of 5-alkyl-2-amino-1,3,4-thiadiazoles and α,ω-bis(2-amino-1,3,4-thiadiazol-5-yl)alkanes in ionic liquids”, Mendeleev Commun., 21:6 (2011), 331–333
Linking options:
  • https://www.mathnet.ru/eng/mendc2962
  • https://www.mathnet.ru/eng/mendc/v21/i6/p331
  • This publication is cited in the following 21 articles:
    1. S-Heterocycles, 2024  crossref
    2. Kalyani Sonawane, Rushikesh Said, Navnath Hatvate, S-Heterocycles, 2024, 163  crossref
    3. Suhail Ahmad, Md. Zafer Alam, Umme Salma, Md. Mohasin, P. Fazul Rahaman, Humaira Parveen, Salman A. Khan, “A review on recent progress in synthesis and biological activities of thiadiazole and its derivatives”, Journal of Molecular Structure, 1312 (2024), 138438  crossref
    4. Parmod Kumar, Harshita Phougat, Anil Kumar, Anurakshee Verma, Karan Singh, “Microwave-Assisted OPC-VH Mediated Synthesis of 2-Amino-1,3,4-thiadiazoles”, Organic Preparations and Procedures International, 55:1 (2023), 91  crossref
    5. Nguyen Dinh Thanh, Vu Ngoc Toan, Nguyen Thi Kim Giang, Hoang Thi Kim Van, Do Son Hai, Nguyen Minh Tri, Duong Ngoc Toan, “Synthesis, biological and molecular modelling for 1,3,4-thiadiazole sulfonyl thioureas: bacterial and fungal activity”, RSC Med. Chem., 14:12 (2023), 2751  crossref
    6. Svetlana Blaja, Lidia Lungu, Alexandru Ciocarlan, Nicoleta Vornicu, Aculina Aricu, “Synthesis and evaluation of antimicrobial activity of tetranorlabdane compounds bearing 1,3,4-thiadiazole units”, Chem. J. Mold., 18:1 (2023), 86  crossref
    7. S. A. Serkov, N. V. Sigai, N. N. Kostikova, A. E. Fedorov, G. A. Gazieva, “Synthesis and evaluation of cytotoxicity of S-substituted 5-sulfanylmethyl(ethyl)-1,3,4-thiadiazol-2-amines”, Russ Chem Bull, 71:8 (2022), 1801  crossref
    8. Damiano Tanini, Tommaso Pecchi, Nikolai Ignat'ev, Antonella Capperucci, “Ionic Liquids-Assisted Ring Opening of Three-Membered Heterocycles with Thio- and Seleno-Silanes”, Catalysts, 12:10 (2022), 1259  crossref
    9. Arti Vishwkarma, A.K. Srivastava, O.P. Pandey, S.K. Sengupta, “Zinc(II) Complexes of Schiff Bases Derived from Bis-(2-hydrazino-1,3,4-thiadiazole-5- yl)Arene/Alkanes: Synthesis, Spectral Characterization and Biological Properties”, Asian J. Chem., 34:8 (2022), 2035  crossref
    10. Kemparajegowda, Hassan A. Swarup, S. Chandrasekhar, B.K. Jayanna, Karthik Kumara, N.K. Lokanath, Sridhar B. Thimmaiah, Kempegowda Mantelingu, “Sulfuric acid-mediated synthesis of 2,5-disubstituted 1,3,4-thiadiazole via intramolecular cyclization reaction from dithioesters: An approach to crystal structure prediction, DFT studies and Hirshfeld surface analysis”, Journal of Molecular Structure, 1251 (2022), 131970  crossref
    11. Tatiana S. Kokovina, Svyatoslav Y. Gadomsky, Alexei A. Terentiev, Nataliya A. Sanina, “A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives”, Molecules, 26:17 (2021), 5159  crossref
    12. Azizollah Habibi, Sahar Khosravi, Seyyed M. Shahcheragh, Mohd B. Abdul Rahman, “One-Pot Green Synthesis of Some Novel N-Substituted 5-Amino-1,3,4- Thiadiazole Derivatives”, LOC, 17:7 (2020), 517  crossref
    13. Samie Yaseen Sharaf Zeebaree, Aymn Yaseen Sharaf Zeebaree, “Synthesis of copper nanoparticles as oxidising catalysts for multi-component reactions for synthesis of 1,3,4- thiadiazole derivatives at ambient temperature”, Sustainable Chemistry and Pharmacy, 13 (2019), 100155  crossref
    14. Samie Yaseen Sharaf Zeebaree, Aymn Yaseen Sharaf Zeebaree, “Withdrawn: Green copper nanoparticles as oxidising catalysts for multi-component reactions for synthesis of 1,3,4-thiadiazole derivatives at ambient temperature”, Results in Materials, 2019, 100001  crossref
    15. Aizhan Abdildinova, Young-Dae Gong, “Current Parallel Solid-Phase Synthesis of Drug-like Oxadiazole and Thiadiazole Derivatives for Combinatorial Chemistry”, ACS Comb. Sci., 20:6 (2018), 309  crossref
    16. Seyyed Mohammad Shahcheragh, Azizollah Habibi, Sahar Khosravi, “Straightforward synthesis of novel substituted 1,3,4-thiadiazole derivatives in choline chloride-based deep eutectic solvent”, Tetrahedron Letters, 58:9 (2017), 855  crossref
    17. M. A. Epishina, A. S. Kulikov, N. V. Ignat'ev, M. Schulte, N. N. Makhova, “Efficient synthesis of tertiary acyclic amides by the Chapman rearrangement of aryl benzimidates in ionic liquids”, Mendeleev Commun., 25:2 (2015), 126–128  mathnet  crossref
    18. Yang Hu, Cui-Yun Li, Xiao-Ming Wang, Yong-Hua Yang, Hai-Liang Zhu, “1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry”, Chem. Rev., 114:10 (2014), 5572  crossref
    19. N. N. Makhova, M. I. Pleshchev, M. A. Epishina, A. S. Kulikov, “Synthesis and Transformations of Nitrogen Heterocycles in Ionic Liquids (Review)”, Chem Heterocycl Comp, 50:5 (2014), 634  crossref
    20. Margarita A. Epishina, Alexander S. Kulikov, Nikolai V. Ignat'ev, Michael Schulte, Nina N. Makhova, “ChemInform Abstract: Synthesis of 5‐Alkyl‐2‐amino‐1,3,4‐thiadiazoles and α,ω‐Bis(2‐amino‐1,3,4‐thiadiazol‐5‐yl)alkanes in Ionic Liquids.”, ChemInform, 43:17 (2012)  crossref
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