Skip to main content
SpringerLink
Log in

New Approach to the Synthesis of 1,3-Chloroisothiocyanatoalkanes. Synthesis of Tetrahydro-1,3-thiazine-2-thiones and 2-Alkylamino-5,6-dihydro-1,3-thiazines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method was developed to prepare 1,3-chloroisothiocyanatoalkanes by reducing 1,3-isothiocyanato ketones using sodium borohydride at pH ~7 and subsequent treatment of the resultant 1,3-isothiocyanato alcohols with thionyl chloride. The reaction of 1,3-chloroisothiocyanatoalkanes with sodium hydrosulfide or amines gives substituted tetrahydro-1,3-thiazine-2-thiones or 2-amino-5,6-dihydro-1,3-thiazines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. P. Gemeiner, K. Halak, and K. Polakova, J. Solid-Phase Biochem., 5, 197 (1980); Chem. Abstr., 96, 81882 (1982).

    Google Scholar 

  2. M. Tomura, O. Mori, H. Chikusa, K. Inazu, A. Ito, N. Matsumura, and H. Inoue, Synthesis, 457 (1991).

  3. R. E. Hackler and T. W. Balbo, Synth. Commun., 5, 143 (1975).

    Google Scholar 

  4. V. L. Narayanan and R. D. Haugwitz, Ger. Offen. 2310015; Chem. Abstr., 79, 137122 (1973).

    Google Scholar 

  5. P. Friis, Acta Chem. Scand., 19, 766 (1965).

    Google Scholar 

  6. A. Kjaer and R. B. Jensen, Acta Chem. Scand., 12, 1746 (1958).

    Google Scholar 

  7. H. Tajima and K. Lee, Jpn. Pat. 09202768; Chem. Abstr., 127, 176196 (1997).

    Google Scholar 

  8. A. B. Khasirdzhev, N. F. Korolenok, and B. V. Unkovsky, USSR Inventor's Certificate No. 423796; Byul. Izobr., No. 14, 82 (1974).

    Google Scholar 

  9. I. P. Boiko, Yu. F. Malina, A. V. Peretokin, B. V. Unkovsky, and A. B. Khasirdzhev, USSR Inventor's Certificate No. 643493; Byul. Izobr., No. 3, 85 (1979).

  10. A. B. Peretokin, T. D. Sokolova, A. S. Fisyuk, Yu. F. Malina, and B. V. Unkovsky, USSR Inventor's Certificate No. 1165678; Byul. Izobr., No. 25, 91 (1985).

  11. A. V. Peretokin, Chemical Sciences Candidate's Dissertation, Moscow (1984).

  12. L. Kniezo, P. Kristian, M. Budesinsky, and K. Havrilova, Coll. Czech. Chem. Commun., 46, 717 (1981).

    Google Scholar 

  13. R. D. Haugwitz and V. L. Narayanan, US Patent 3767654; Chem. Abstr., 80, 27263 (1974).

    Google Scholar 

  14. M. Kahan, Ber., 30, 1318 (1897).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Omsk State University, Omsk, 644077, Russia

    A. S. Fisyuk, N. V. Peretokin & B. V. Unkovsky

Authors
  1. A. S. Fisyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. V. Peretokin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. V. Unkovsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fisyuk, A.S., Peretokin, N.V. & Unkovsky, B.V. New Approach to the Synthesis of 1,3-Chloroisothiocyanatoalkanes. Synthesis of Tetrahydro-1,3-thiazine-2-thiones and 2-Alkylamino-5,6-dihydro-1,3-thiazines. Chemistry of Heterocyclic Compounds 39, 802–808 (2003). https://doi.org/10.1023/A:1025663616439

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1025663616439

Search

Navigation