Skip to main content
SpringerLink
Log in

Regioselective chlorination at C-6 methyl position of 3,4-dihydropyrimidin-2(1H)-ones using (dichloroiodo)benzene

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The reaction of (dichloroiodo)benzene with 4-aryl-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylates and 5-acetyl-4-aryl-3,4-dihydro-6-methylpyrimidin-2(1H)-ones resulted in geminal dichlorination at the C-6 methyl position of 3,4-dihydropyrimidin-2(1H)-one.

Graphical abstract

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

Fig. 1

Similar content being viewed by others

References

  1. Kappe CO (2000) Eur J Med Chem 35:1043

    Article  CAS  Google Scholar 

  2. Kappe CO (2000) Acc Chem Res 33:879

    Article  CAS  Google Scholar 

  3. Kappe CO (1993) Tetrahedron 49:6937

    Article  CAS  Google Scholar 

  4. Zanatta N, Fantinel L, Fernandes LS, Wouters AD, Bonacorso HG, Martins MAP (2008) Synthesis 21:3492

    Article  Google Scholar 

  5. Zigeuner G, Hamberger H, Blaschke H, Sterk H (1966) Monatsh Chem 97:1406

    Google Scholar 

  6. Namazi H, Mirzaei YR, Azamat H (2001) J Heterocycl Chem 38:1051

    Article  CAS  Google Scholar 

  7. Zigeuner G, Knopp C (1970) Monatsh Chem 101:1541

    Article  CAS  Google Scholar 

  8. George T, Tahrlramani R, Metha DV (1975) Synthesis 405

  9. Kappe CO (1990) Liebigs Ann Chem 505

  10. Khanetskyy B, Dallinger D, Kappe CO (2004) J Comb Chem 6:884

    Article  CAS  Google Scholar 

  11. Bullock E, Carter RA, Cochrane RM, Gregory B, Shields DC (1977) Can J Chem 55:895

    Article  CAS  Google Scholar 

  12. Singh K, Singh S, Mahajan A (2005) J Org Chem 70:6114

    Article  CAS  Google Scholar 

  13. Khanina EL, Duburs G (1982) Khim Geterotsikl Soedin 535

  14. Khanina EL, Liepin’sh EE, Mutsenretse DK, Duburs G (1987) Khim Geterotsikl Soedin 668

  15. Chen JM, Zeng XM, Middleton K, Zhdankin VV (2011) Tetrahedron Lett 52:1952

    Article  CAS  Google Scholar 

  16. Puchala A, Belaj F, Bergman J, Kappe CO (2001) J Heterocycl Chem 38:1345

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are thankful to the Department of Science and Technology, New Delhi, India for the financial support (No. SR/S1/OC-72/2009). The authors are also thankful to Mr. Avtar Singh, SAIF, Punjab University, Chandigarh, India for recording NMR spectra.

Author information

Authors and Affiliations

  1. Department of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur, Maharashtra, 440 033, India

    Nilesh P. Tale, Amol V. Shelke, Bhagyashree Y. Bhong & Nandkishor N. Karade

Authors
  1. Nilesh P. Tale
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amol V. Shelke
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bhagyashree Y. Bhong
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nandkishor N. Karade
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nandkishor N. Karade.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 7644 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tale, N.P., Shelke, A.V., Bhong, B.Y. et al. Regioselective chlorination at C-6 methyl position of 3,4-dihydropyrimidin-2(1H)-ones using (dichloroiodo)benzene. Monatsh Chem 144, 981–986 (2013). https://doi.org/10.1007/s00706-012-0908-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0908-0

Keywords

Search

Navigation