220
Views
1
CrossRef citations to date
0
Altmetric
Review

Developments in the electrochemical synthesis of thia-heterocycles

, , , &
Pages 891-898 | Received 03 Feb 2022, Accepted 21 Mar 2022, Published online: 01 Apr 2022

References

  • Tabaković, I.; Electrochemistry, V. I. Electroorganic Synthesis: Bond Formation at Anode and Cathode. Berlin: Springer; 1997.
  • Lund, H.; Hammerich, O. Organic Electrochemistry, 4th ed. Marcel Dekker, Inc., 2001.
  • Moinet, C.; Stratmann, M. Encyclopedia of Electrochemistry (Ed. A. J. Bard). Wiley-VCH: Weinheim, 2004; p 341.
  • Sperry, J. B.; Wright, D. L. The Application of Cathodic Reductions and Anodic Oxidations in the Synthesis of Complex Molecules. Chem. Soc. Rev. 2006, 35, 605–621. DOI: 10.1039/B512308A.
  • Yoshida, J. I.; Kataoka, K.; Horcajada, R.; Nagaki, A. Modern Strategies in Electroorganic Synthesis. Chem. Rev. 2008, 108, 2265–2299. DOI: 10.1021/cr0680843.
  • Francke, R.; Little, R. D. Redox Catalysis in Organic Electrosynthesis: Basic Principles and Recent Developments. Chem. Soc. Rev. 2014, 43, 2492–2521. DOI: 10.1039/C3CS60464K.
  • Francke, R. Recent Advances in the Electrochemical Construction of Heterocycles. Beilstein J. Org. Chem. 2014, 10, 2858–2873. DOI: 10.3762/bjoc.10.303.
  • Yan, M.; Kawamata, Y.; Baran, P. S. Synthetic Organic Electrochemical Methods since 2000: On the Verge of a Renaissance. Chem. Rev. 2017, 117, 13230–13319. DOI: 10.1021/acs.chemrev.7b00397.
  • Jiang, Y.; Xu, K.; Zeng, C. Use of Electrochemistry in the Synthesis of Heterocyclic Structures. Chem. Rev. 2018, 118, 4485–4540. DOI: 10.1021/acs.chemrev.7b00271.
  • Sbei, N.; Listratova, A. V.; Titov, A. A.; Voskressensky, L. G. Recent Advances in Electrochemistry for the Synthesis of N-Heterocycles. Synthesis. 2019, 51, 2455–2473. DOI: 10.1055/s-0037-1611797.
  • Pastor, M.; Vayer, M.; Weinstabl, H.; Maulide, N. Electrochemical Umpolung C-H Functionalization of Oxindoles. J. Org. Chem. 2022, 87, 606–612. DOI: 10.1021/acs.joc.1c02616.
  • Le Guillanton, G. Electrochemical Activation of Sulfur in Organic Solvents-New Syntheses of Thioorganic Compounds with a Sacrificial Carbon-Sulfur Electrode. Sulfur Report. 1992, 12, 405–431. DOI. 10.1080/01961779208048949.
  • Yuan, Y.; Yang, J.; Lei, A. Recent Advances in Electrochemical Oxidative Cross-Coupling with Hydrogen Evolution Involving Radicals. Chem. Soc. Rev. 2021, 50, 10058–10086. DOI: 10.1039/D1CS00150G.
  • Lingaraju, G. S.; Swaroop, T. R.; Vinayaka, A. C.; Kumar, K. S. S.; Sadashiva, M. P.; Rangappa, K. S. An Easy Access to 4, 5-Disubstituted Thiazoles via Base-Induced Click Reaction of Active Methylene Isocyanides with Methyl Dithiocarboxylates. Synthesis. 2012, 44, 1373–1379. DOI: 10.1055/s-0031-1290762.
  • Kumar, K. S. S.; Swaroop, T. R.; Harsha, K. B.; Narasimhamurthy, K. H.; Rangappa, K. S. T3P®-DMSO Mediated One Pot Cascade Protocol for the Synthesis of 4-Thiazolidinones from Alcohols. Tetrahedron. Lett. 2012, 53, 5619–5623. DOI. 10.1016/j.tetlet.2012.08.020.
  • Swaroop, T. R.; Roopashree, R.; Ila, H.; Rangappa, K. S. Attempted Simmon–Smith Reaction on β-Alkylthio-α,β-Unsaturated Ketones: A Regiospecific Synthesis of 2,4-Disubstituted Thiophenes. Tetrahedron. Lett. 2013, 54, 147–150. DOI: 10.1016/j.tetlet.2012.10.110.
  • Swaroop, T. R.; Ila, H.; Rangappa, K. S. Cyclocondensation of β-(Aryl/Heteroaryl) Methylaminoenones with Thionyl Chloride: A Facile General Approach for the Synthesis of 2,4-Bis(Het)Aryl-5(Het)Aroylthiazoles. Tetrahedron. Lett. 2013, 54, 5288–5292. DOI. 10.1016/j.tetlet.2013.07.079.
  • Rajeev, N.; Swaroop, T.; Anil, S.; Bommegowda, Y.; Rangappa, K.; Sadashiva, M. Base-Induced Cyclization of Active Methylene Isocyanides with Xanthate Esters: An Efficient Method for the Synthesis of 5-Alkoxy-4-(Tosyl/Ethoxycarbonyl)-1,3-Thiazoles. Synlett. 2017, 28, 2281–2284. DOI: 10.1055/s-0036-1590811.
  • Kiran, K. R.; Swaroop, T. R.; Rajeev, N.; Anil, S. M.; Rangappa, K. S.; Sadashiva, M. P. Cyclization of Active Methylene Isocyanides with α-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-Acylthiazoles. Synthesis. 2020, 52, 1444–1450. DOI: 10.1055/s-0039-1690821.
  • Balsamo, A.; Benedini, P. M.; Giorgi, I.; Macchia, B.; Macchia, F. Interconversion of the Thiazine and Thiazolidine System of β-Lactam Antibiotics, Electrochemical Cleavage of Kamiya’s Disulphide Promoted by Bromide Ion. Tetrahedron. Lett. 1982, 23, 2991–2994. DOI. 10.1016/S0040-4039(00)87514-0.
  • Machion, P. D. Ph.D. thesis. Instituto de Quimica, Universidade de Sao Paulo, Brazil, 1993.
  • Hlavat, J. R.; Bakos, V.; Volke, J. Anodic Oxidation of o-Toluenesulfonamide to Saccharine on a NiO(OH)-Coated Nickel Anode. J. Appl. Electrochem. 1987, 17, 1228–1233. DOI. 10.1007/BF01023607.
  • Sicker, D.; Hartenstein, H.; Mouats, C.; Hazard, R.; Tallec, A. Electrochemical Reduction of o-Nitrophenylthioacetic Derivatives. Production of 2H-1,4-Benzothiazines. Electrochim. Acta. 1995, 40, 1669–1674. DOI. 10.1016/0013-4686(95)00083-Q.
  • Brand, K.; Stohr, E. Die Elektrochemische Reduction Des o‐Nitroacetanilids. Ber. Dtsch. Chem. Ges. 1906, 39, 4058–4068. DOI: 10.1002/cber.19060390494.
  • Voss, J.; Dannat, V. Electroreduction of Organic Compounds, Part 39; Formation of Benzo[b]Thiophenes by Electroreduction of 2-Bromobenzyl tert-Alkanecarbodithioates. Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 2142–2153; 2016, 191, 333, and lit. cited therein. DOI: 10.1080/10426507.2015.1071370.
  • Laćan, M.; Jakopčić, K.; Rogić, V.; Damoni, S.; Rogić, O.; Tabaković, I. Electrochemical Synthesis of Heterocyclic Compounds II. Synthesis of Some N-Heterocycles by Intramolecular Oxidative Cyclisation. Synth. Commun. 1974, 4, 219–224. DOI. 10.1080/00397917408062076.
  • Tabaković, I.; Trkovnik, M.; Batusic, M.; Tabaković, I. Electrochemical Synthesis of Heterocyclic Compounds; VII1. Anodic Synthesis of 1,3-Thiazole Derivatives. Synthesis. 1979, 1979, 590–592. DOI: 10.1055/s-1979-28768.
  • Hlavatý, J.; Volke, J.; Manoušek, O. Electrochemical Behavior of 2,2′-Dinitrodiphenylsulfide and Its Cyclization Reactions Initiated by an Electrode Reduction. Electrochim. Acta. 1978, 23, 589–598. DOI. 10.1016/0013-4686(78)80086-3.
  • Hlavatý, J.; Volke, J. The Electrochemical Behavior of 2,2'-(Bishydroxylamino) Diphensulphide. Electrochim. Acta. 1984, 29, 1399–1404. DOI: 10.1016/0013-4686(84)87018-8.
  • Mugnier, Y.; Laviron, E. Etude Electrochimique du Dinitro-2,2′-Diphenyle Sulfure. Electrochim. Acta. 1980, 25, 1329–1332. DOI: 10.1016/0013-4686(80)87143-X.
  • Katayama, A.; Senboku, H.; Hara, S. Aryl Radical Cyclization with Alkyne Followed by Tandem Carboxylation in Methyl 4-tert-Butylbenzoate-Mediated Electrochemical Reduction of 2-(2-Propynyloxy)Bromobenzenes in the Presence of Carbon Dioxide. Tetrahedron. 2016, 72, 4626–4636. DOI: 10.1016/j.tet.2016.06.032.
  • Morofuji, T.; Shimizu, A.; Yoshida, J. I. Electrochemical Intramolecular C-H Amination: Synthesis of Benzoxazoles and Benzothiazoles. Chemistry. 2015, 21, 3211–3214. DOI: 10.1002/chem.201406398.[PMC][25641711]
  • Goda, S.; Yamada, K.; Yamamoto, Y.; Maekawa, H.; Nishiguchi, I. Intramolecular Electroreductive Cyclization of Heteroatom-Containing Non-Conjugated Enones and Ynones. J. Electroanal. Chem. 2003, 545, 129–140. DOI. 10.1016/S0022-0728(03)00082-2.
  • Kunugi, A.; Jabbar, M. A.; Mori, K.; Uno, H. Electrosynthesis of Isothiazoles from Sulfonyl-Substituted 2-Alkenenitrile Using a Reactive Sulfur–Graphite Electrode. Electrochim. Acta. 1999, 44, 4583–4592. DOI: 10.1016/S0013-4686(99)00180-2.
  • Matsumoto, K.; Ueoka, K.; Fujie, S.; Suga, S.; Yoshida, J.-I. Synthesis of Thiochromans Based on Indirect Cation Pool Method. Heterocycles. 2008, 76, 1103–1119. DOI: 10.3987/COM-08-S(N)64.
  • Wawzonek, S.; Heilmann, S. M. Electrochemical Reduction of Carbon Disulfide in Dimethylformamide. J. Org. Chem. 1974, 39, 511–514. DOI. 10.1021/jo00918a021.
  • Moses, P. R.; Chambers, J. Q. Electrochemical Synthesis and Characterization. J. Am. Chem. Soc. 1974, 96, 945–946. DOI. 10.1021/ja00810a066.
  • Voss, J.; Mischke, P.; Adiwidjaja, G. Elektrochemische Oxidation Von Dithiocarbonsäureestern zu Isothiazolen. Phosphorus Sulfur Silicon Relat. Elem. 1986, 27, 261–274. DOI. 10.1080/03086648608072779.
  • Le Guillanton, G.; Do, Q. T.; Simonet, J. Use of Carbon-Sulfur Cathodes in Organic Electrochemistry I. Application to the Reduction of Vinylic Compounds with Leaving Groups of Z-3-Chloro (or 3-Tosyloxy or 3-Benzoyloxy)-2-Phenylpropeninitrile. Bull. Soc. Chim. Fr. 1989, 433–440.
  • Shahrokhian, S.; Hamzehloei, A. Electrochemical Oxidation of Catechol in the Presence of 2-Thiouracil: Application to Electro-Organic Synthesis. Electrochem. Commun. 2003, 5, 706–710. DOI: 10.1016/S1388-2481(03)00170-X.
  • Wang, H.-B.; Huang, J.-M. Coupling of α‐Keto Acids with Ortho‐Phenylenediamines Promoted by an Electrochemical Method in Aqueous Media. Adv. Synth. Catal. 2016, 358, 1975–1981. DOI: 10.1002/adsc.201501167.
  • Lai, Y. L.; Ye, J. S.; Huang, J. M. Electrochemical Synthesis of Benzazoles from Alcohols and o‐Substituted Anilines with a Catalytic Amount of CoII Salt. Chem. Eur. J. 2016, 22, 5425–5429. DOI: 10.1002/chem.201505074.
  • Mo, S.-K.; Teng, Q.-H.; Pan, Y.-M.; Tang, H.-T. Metal- and Oxidant-Free Electrosynthesis of 1,2,3-Thiadiazoles from Element Sulfur and N-Tosylhydrazones. Adv. Synth. Catal. 2019, 361, 1756–1765. DOI. 10.1002/adsc.201801700.
  • Wang, Z. Q.; Meng, X. J.; Li, Q. Y.; Tang, H.-T.; Wang, H.-S.; Pan, Y.-M. Electrochemical Synthesis of 3,5‐Disubstituted 1,2,4‐Thiadiazoles through NH4I‐Mediated Dimerization of Thioamides. Adv. Synth. Catal. 2018, 360, 4043–4048. DOI. 10.1002/adsc.201800871.
  • Wen, L.-R.; Wang, N.-N.; Du, W.-B.; Zhu, M.-Z.; Pan, C.; Zhang, L. B.; Li, M. Electrochemical Selective Oxidative Synthesis of Diversified Sulfur Heterocycles from β-Ketothioamides. Chin. J. Chem. 2021, 39, 1831–1837. DOI. 10.1002/cjoc.202100132.
  • Cao, Y.; Yuan, Y.; Lin, Y.; Jiang, X.; Weng, Y.; Wang, T.; Bu, F.; Zeng, L.; Lei, A. Cobalt Catalyzed Electrochemical [4 + 2] Annulation for the Synthesis of Sultams. Green Chem. 2020, 2020, 1548–1552. DOI: https://doi.org/10.1039/D0GC00289E.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.