Skip to main content

ZnO-nanorods as economical catalyst for synthesis of 4-amino-2-iminodithiole derivatives using tetramethyl thiourea in water

Chemical Papers volume 70, pages 907–912 (2016)Cite this article

Abstract

4-amino-2-iminodithiole derivatives were synthesised via multi-component reactions of tetramethyl thiourea, isothiocyanates and alkyl bromides in the presence of ZnO nanorods (ZnO-NR) as the catalyst in water at ambient temperature. These reactions provide low yields without catalysts. The catalyst exhibited significant reusable activity.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

References

  • Abbaz, T., Bendjeddou, A., Gouasmia, A., Regainia, Z., & Villemin, D. (2012). Synthesis and electrochemical proprieties of novel unsymmetrical bis-tetrathiafulvalenes and electrical conductivity of their charge transfer complexes with tetracyanoquinodimethane (TCNQ). International Journal of Molecular Sciences, 13, 7872–7885. DOI: 10.3390/ijms13077872.

    CAS  Article  Google Scholar 

  • Beydoun, D., Amal, R., Low, G., & McEvoy, S. (1999). Role of nanoparticles in photocatalysis. Journal of Nanoparticle Research, 1, 439–458. DOI: 10.1023/a:1010044830871.

    CAS  Article  Google Scholar 

  • Breslow, R. (1991). Hydrophobic effects on simple organic reactions in water. Accounts of Chemical Research, 24, 159–164. DOI: 10.1021/ar00006a001.

    CAS  Article  Google Scholar 

  • Capuano, L., Bronder, M., Hell, W., Mörsdorf, P., & Hoge, R. (1980). Neue Heterocyclisierungen mit Malonestern 1,3-Dithiole; 1,3-Oxathiole; Δ2-Oxazoline und das Vinylendi-pyridiniumdikation. Monatshefte für Chemie — Chemical Monthly, 111, 899–907. DOI: 10.1007/bf00899255. (in German)

    CAS  Article  Google Scholar 

  • Comparelli, R., Fanizza, E., Curri, M. L., Cozzoli, P. D., Mascolo, G., & Agostiano, A. (2005). UV-induced photocatalytic degradation of azo dyes by organic-capped ZnO nanocrystals immobilized onto substrates. Applied Catalysis B, 60, 1–11. DOI: 10.1016/j.apcatb.2005.02.013.

    CAS  Article  Google Scholar 

  • Demko, Z. P., & Sharpless, K. B. (2001). Preparation of 5-substituted 1H-tetrazoles from nitriles in water. Journal of Organic Chemistry, 66, 7945–7950. DOI: 10.1021/jo010635w.

    CAS  Article  Google Scholar 

  • Ferraris, J., Cowan, D. O., Walatka, V., & Perlstein, J. H. (1973). Electron transfer in a new highly conducting donor—acceptor complex. Journal of the American Chemical Society, 95, 948–949. DOI: 10.1021/ja00784a066.

    CAS  Article  Google Scholar 

  • Grieco, P. A. (1998). Organic synthesis in water. London, UK: Blackie Academic & Professional.

    Book  Google Scholar 

  • Guillemet, M., Raoul, J. M., Pellé, F., Robert, A., & Baudy-Floc’h, M. (1995). Simple synthesis of new 2-imino-4-amino-1,3-dithioles and 2-lmino-4-hydroxy-1,3-dithioles. Journal of Materials Chemistry, 5, 35–39. DOI: 10.1039/jm9950500035.

    CAS  Article  Google Scholar 

  • Gupta, M., Paul, S., Gupta, R., & Loupy, A. (2005). ZnO: A versatile agent for benzylic oxidations. Tetrahedron Letters, 46, 4957–4960. DOI: 10.1016/j.tetlet.2005.05.104.

    CAS  Article  Google Scholar 

  • Hosseini-Sarvari, M., Sharghi, H., & Etemad, S. (2008). Nanocrystalline ZnO for Knoevenagel condensation and reduction of the carbon, carbon double bond in conjugated alkenes. Helvetica Chimica Acta, 91, 715–724. DOI: 10.1002/hlca.200890072.

    CAS  Article  Google Scholar 

  • Kobayashi, S., & Manabe, K. (2002). Development of novel lewis acid catalysts for selective organic reactions in aqueous media. Accounts of Chemical Research, 35, 209–217. DOI: 10.1021/ar000145a.

    CAS  Article  Google Scholar 

  • Li, C. J., & Chang, T. H. (1997). Organic reactions in aqueous media. New York, NY, USA: Wiley.

    Google Scholar 

  • Li, C. J. (2005). Organic reactions in aqueous media with a focus on carbon—carbon bond formations: A decade update. Chemical Reviews, 105, 3095–3166. DOI: 10.1021/cr030009u.

    CAS  Article  Google Scholar 

  • Lietti, L., Tronconi, E., Forzatti, P., & Busca, G. (1989). Surface properties of ZnO-based catalysts and related mechanistic features of the higher alcohol synthesis by FT-IR spectroscopy and TPSR. Journal of Molecular Catalysis, 55, 43–54. DOI: 10.1016/0304-5102(89)80241-x.

    CAS  Article  Google Scholar 

  • Lindström, U. M. (2002). Stereoselective organic reactions in water. Chemical Reviews, 102, 2751–2772. DOI: 10.1021/cr010122p.

    Article  Google Scholar 

  • Matin, B. M., Mortazavi, Y., Khodadadi, A. A., Abbasi, A., & Firooz, A. A. (2010). Alkaline- and template-free hydrothermal synthesis of stable SnO2 nanoparticles and nanorods for CO and ethanol gas sensing. Sensors and Actuators B, 151, 140–145. DOI: 10.1016/j.snb.2010.09.033.

    CAS  Article  Google Scholar 

  • Mirjafary, Z., Saeidian, H., Sadeghi, A., & Moghaddam, F. M. (2008). ZnO nanoparticles: An efficient nanocatalyst for the synthesis of β-acetamido ketones/esters via a multicomponent reaction. Catalysis Communications, 9, 299–306. DOI: 10.1016/j.catcom.2007.06.018.

    CAS  Article  Google Scholar 

  • Moghaddam, F. M., & Saeidian, H. (2007). Controlled micro-wave-assisted synthesis of ZnO nanopowder and its catalytic activity for O-acylation of alcohol and phenol. Materials Science and Engineering: B, 139, 265–269. DOI: 10.1016/j.mseb.2007.03.002.

    CAS  Article  Google Scholar 

  • Narayan, S., Muldoon, J., Finn, M. G., Fokin, V. V., Kolb, H. C., & Sharpless, K. B. (2005). “On water”: Unique reactivity of organic compounds in aqueous suspension. Angewandte Chemie International Edition, 44, 3275–3279. DOI: 10.1002/anie.200462883.

    CAS  Article  Google Scholar 

  • Oliveira, S., Belo, D., Santos, I. C., Rabaça, S., & Almeida, M. (2015). Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor. Beilstein Journal of Organic Chemistry, 11, 951–956. DOI: 10.3762/bjoc.11.106.

    CAS  Article  Google Scholar 

  • Pirrung, M. C. (2006). Acceleration of organic reactions through aqueous solvent effects. Chemistry — A European Journal, 12, 1312–1317. DOI: 10.1002/chem.200500959.

    CAS  Article  Google Scholar 

  • Polshettiwar, V., & Varma, R. S. (2008). Microwave-assisted organic synthesis and transformations using benign reaction media. Accounts of Chemical Research, 41, 629–639. DOI: 10.1021/ar700238s.

    CAS  Article  Google Scholar 

  • Rostamizadeh, S., Nojavan, M., Aryan, R., Isapoor, E., & Azad, M. (2013). Amino acid-based ionic liquid immobilized on α-Fe2O3-MCM-41: An efficient magnetic nanocatalyst and recyclable reaction media for the synthesis of quinazolin-4(3H)-one derivatives. Journal of Molecular Catalysis A, 374–375, 102–110. DOI: 10.1016/j.molcata.2013.04.002.

    Article  Google Scholar 

  • Sabbaghan, M., Anaraki Firooz, A., & Jan Ahmadi, V. (2012). The effect of template on morphology, optical and photocatalytic properties of ZnO nanostructures. Journal of Molecular Liquids, 175, 135–140. DOI: 10.1016/j.molliq.2012.08.019.

    CAS  Article  Google Scholar 

  • Shaterian, H. R., & Mohammadnia, M. (2013). Effective preparation of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene and hydroxyl naphthalene-1,4-dione derivatives under ambient and solvent-free conditions. Journal of Molecular Liquids, 177, 353–360. DOI: 10.1016/j.molliq.2012.10.012.

    CAS  Article  Google Scholar 

  • Urgast Hoge, R., Eichhorn, K., & Fischer, K. (1980). 5-Benzamido-2-benzoyl-imino-1,3-dithiol 4-carbonic acid-ethylester, C20H16N2O4S2. Crystal Structure Communications, 9, 615–619.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Gonbad Kavous University, P.O. Box 163, Gonbad, Iran

    Faramarz Rostami-Charati

  2. Department of Chemistry, Qaemshahr Branch, Islamic Azad University, P.O. Box 163, Qaemshahr, Iran

    Rahimeh Hajinasiri

  3. Department of Chemistry, Azadshahr Branch, Islamic Azad University, Azadshahr, Iran

    Seyyed Zahra Sayyed Alangi & Saeid Afshari Sharif Abad

Authors
  1. Faramarz Rostami-Charati
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rahimeh Hajinasiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Seyyed Zahra Sayyed Alangi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Saeid Afshari Sharif Abad
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Faramarz Rostami-Charati.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Rostami-Charati, F., Hajinasiri, R., Sayyed Alangi, S.Z. et al. ZnO-nanorods as economical catalyst for synthesis of 4-amino-2-iminodithiole derivatives using tetramethyl thiourea in water. Chem. Pap. 70, 907–912 (2016). https://doi.org/10.1515/chempap-2016-0030

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1515/chempap-2016-0030

Keywords

  • alkyl bromide
  • ZnO nanorod (ZnO−NR)
  • tetramethyl thiourea
  • multicomponent reaction
  • isothiocyanate