A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

András György Németh, György Miklós Keserű and Péter Ábrányi-Balogh
Beilstein J. Org. Chem. 2019, 15, 1523–1533. https://doi.org/10.3762/bjoc.15.155

Supporting Information

Supporting Information File 1: Experimental procedures, characterization data and copies of NMR spectra.
Format: PDF Size: 3.2 MB Download

Cite the Following Article

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates
András György Németh, György Miklós Keserű and Péter Ábrányi-Balogh
Beilstein J. Org. Chem. 2019, 15, 1523–1533. https://doi.org/10.3762/bjoc.15.155

How to Cite

Németh, A. G.; Keserű, G. M.; Ábrányi-Balogh, P. Beilstein J. Org. Chem. 2019, 15, 1523–1533. doi:10.3762/bjoc.15.155

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 169.0 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Alekseev, E.; Komarova, A. Effect of Potato Storage Conditions on the Quality of Dithiocarbamate Analysis. Potato Research 2023. doi:10.1007/s11540-023-09666-0
  • Lopez de Pariza, X.; Fanlo, P.; Polo Fonseca, L.; Ruiz de Luzuriaga, A.; Sardon, H. Polythiourethanes: Synthesis, applications, and opportunities. Progress in Polymer Science 2023, 145, 101735. doi:10.1016/j.progpolymsci.2023.101735
  • Liu, X.; Cai, T.-C.; Zhu, M.; Liu, Y.; Xia, J.; Xie, J.; Wen, L.; Gui, Q.-W.; Yin, Y. S-alkyl Dithiocarbamates Synthesis through Electrochemical Multicomponent Reaction of Thiols, Hydrogen Sulfide, and Isocyanides. The Journal of organic chemistry 2023, 88, 12311–12318. doi:10.1021/acs.joc.3c01017
  • P, H.; Hati, S.; Dey, R. S-Alkylation of dithiocarbamates via a hydrogen borrowing reaction strategy using alcohols as alkylating agents. Organic & biomolecular chemistry 2023, 21, 6360–6367. doi:10.1039/d3ob00958k
  • Song, P.; Rao, W.; Chivers, T.; Wang, S.-Y. Applications of trisulfide radical anion S3˙− in organic synthesis. Organic Chemistry Frontiers 2023, 10, 3378–3400. doi:10.1039/d3qo00496a
  • Arar, W.; Viau, L.; Jourdain, I.; Knorr, M.; Strohmann, C.; Scheel, R.; Ben Akacha, A. Synthesis of Catena-bis(μ-bromo)-(O-methyl-N-phenylthiocarbamate)-dicopper(I) and Its Reactivity towards PAr3 (Ar = Ph, p-Tol). Molbank 2023, 2023, M1655. doi:10.3390/m1655
  • Wolfs, J.; Ribca, I.; Meier, M. A. R.; Johansson, M. Polythionourethane Thermoset Synthesis via Activation of Elemental Sulfur in an Efficient Multicomponent Reaction Approach. ACS Sustainable Chemistry & Engineering 2023, 11, 3952–3962. doi:10.1021/acssuschemeng.3c00143
  • Gul, A.; Saad, S. M.; Zafar, H.; Atia-Tul-Wahab; Khan, K. M.; Choudhary, M. I. In vitro and In silico Xanthine Oxidase Inhibitory Activities of 3-Aryl-2- thioxo-2,3-dihydroquinazolin-4(1H)-one Derivatives. Medicinal chemistry (Shariqah (United Arab Emirates)) 2023, 19, 384–392. doi:10.2174/1573406418666220620124034
  • Ambhaikar, N. B.; Uppaluri, S. Five-membered ring systems: with N and S atom. Progress in Heterocyclic Chemistry; Elsevier, 2023; pp 305–340. doi:10.1016/b978-0-443-18939-5.00009-3
  • Zhu, X.; He, J.; Yang, Y.; Zhou, S.; Wei, Y.; Wang, S. Synthesis of rare-earth metal complexes with a morpholine-functionalized β-diketiminato ligand and their catalytic activities towards C-O and C-N bond formation. Dalton transactions (Cambridge, England : 2003) 2022, 51, 13227–13235. doi:10.1039/d2dt02053j
  • Arar, W.; Khatyr, A.; Knorr, M.; Strohmann, C.; Schmidt, A. Bis(μ-iodo)-tetrakis(O-methyl N-phenylthiocarbamate)-tetraiodo-dibismuth. Molbank 2022, 2022, M1381. doi:10.3390/m1381
  • Németh, A. G.; Szabó, R.; Németh, K.; Keserű, G. M.; Ábrányi-Balogh, P. A stepwise one-pot synthesis of aliphatic thiols and their derivatives from acrylamides and sulfur. Organic & biomolecular chemistry 2022, 20, 4361–4368. doi:10.1039/d2ob00512c
  • Kyriakou, S.; Trafalis, D. T.; Deligiorgi, M. V.; Franco, R.; Pappa, A.; Panayiotidis, M. I. Assessment of Methodological Pipelines for the Determination of Isothiocyanates Derived from Natural Sources. Antioxidants (Basel, Switzerland) 2022, 11, 642. doi:10.3390/antiox11040642
  • Németh, A. G.; Ábrányi-Balogh, P. Recent Advances in the Synthesis of Isothiocyanates Using Elemental Sulfur. Catalysts 2021, 11, 1081. doi:10.3390/catal11091081
  • Németh, A. G.; Marlok, B.; Domján, A.; Gao, Q.; Han, X.; Keserű, G. M.; Ábrányi-Balogh, P. Convenient Multicomponent One-Pot Synthesis of 2-Iminothiazolines and 2-Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions. European Journal of Organic Chemistry 2021, 2021, 3587–3597. doi:10.1002/ejoc.202100548
  • Neetha, M.; Radhika, S.; Anilkumar, G. Atom Economic Green Organic Reactions. Green Organic Reactions; Springer Singapore, 2021; pp 201–219. doi:10.1007/978-981-33-6897-2_12
  • Zhang, J.; Zang, Q.; Yang, F.; Zhang, H.; Sun, J. Z.; Tang, B. Z. Sulfur Conversion to Multifunctional Poly(O-thiocarbamate)s through Multicomponent Polymerizations of Sulfur, Diols, and Diisocyanides. Journal of the American Chemical Society 2021, 143, 3944–3950. doi:10.1021/jacs.1c00243
  • Nickisch, R.; Conen, P.; Gabrielsen, S. M.; Meier, M. A. R. A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur. RSC advances 2021, 11, 3134–3142. doi:10.1039/d0ra10436a
  • Németh, A. G.; Szabó, R.; Domján, A.; Keserű, G. M.; Ábrányi-Balogh, P. Chromatography-Free Multicomponent Synthesis of Thioureas Enabled by Aqueous Solution of Elemental Sulfur. ChemistryOpen 2020, 10, 16–27. doi:10.1002/open.202000250
  • Dutta, S.; Saha, A. Iodine mediated direct coupling of benzylic alcohols with dithiocarbamate anions: An easy access of S-benzyl dithiocarbamate esters under neat reaction condition. Tetrahedron Letters 2020, 61, 152382. doi:10.1016/j.tetlet.2020.152382

Patents

  • ZHANG JIE; SUN JINGZHI. POLYTHIOCARBAMATE COMPOUND, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF. WO 2022116463 A1, June 9, 2022.
Other Beilstein-Institut Open Science Activities