Skip to main content
SpringerLink
Log in

Synthesis of new functionalized alizarins from alizarin, acetylenic esters, and phosphorus nucleophiles

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

Abstract

The 1:1 intermediate generated by the addition of triphenylphosphine to dialkyl acetylenedicarboxylates is trapped by alizarin to produce alkyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylates in good yields. When ethyl propiolate was used, the reaction afforded ethyl 6,11-dihydro-6,11-dioxoanthra[1,2-d][1,3]-dioxole-2-acetate. The reaction of dialkyl acetylenedicarboxylates, alizarin, and trialkyl phosphites produced dialkyl 2-(dialkoxyphosphoryl)-3-(9,10-dihydro-1-hydroxy-9,10-dioxoanthracen-2-yloxy)succinates.

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

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. Yates FS (1984) In: Boulton AJ, McKillop A (eds), Comprehensive Heterocyclic Chemistry, vol 2, part 2A. Pergamon, Oxford, p 511

  2. Butler J, Hoey BM (1987) Br J Cancer 55:53

    Article  CAS  Google Scholar 

  3. Yavari I, Hekmat-Shoar R, Zonouzi A (1998) Tetrahedron Lett 39:2391

    Article  CAS  Google Scholar 

  4. Baharfar R, Vahdat SM, Hakimabadi FG (2009) Monatsh Chem 140:489

    Article  CAS  Google Scholar 

  5. Yavari I, Feiz-Javadian F (2006) Phosphorus. Sulfur Silicon Relat Elem 181:1011

    Article  CAS  Google Scholar 

  6. Yavari I, Adib M, Hojabri L (2002) Tetrahedron 58:6895

    Article  CAS  Google Scholar 

  7. Yavari I, Adib M, Hojabri L (2001) Tetrahedron 57:5737

    Google Scholar 

  8. Nourmohammadian F, Davoodzadeh-Gholami M (2008) Synth Commun 38:2731

    Article  CAS  Google Scholar 

  9. Yavari I, Bayat M (2002) Synth Commun 32:2527

    Article  CAS  Google Scholar 

  10. Yavari I, Hossaini Z, Seyfi S, Shirgahi-Talari F (2008) Monatsh Chem 139:1257

    Article  CAS  Google Scholar 

  11. Yavari I, Nourmohammadian F (2000) Tetrahedron 56:5221

    Article  CAS  Google Scholar 

  12. Yavari I, Samzadeh-Kermani AR (1984) Tetrahedron Lett 39:6343

    Article  Google Scholar 

  13. Yavari I, Hossaini Z, Karimi E (2007) Monatsh Chem 138:1267

    Article  CAS  Google Scholar 

  14. Yavari I, Anary-Abbasinejad M, Hossaini Z (2004) Pol J Chem 78:361

    CAS  Google Scholar 

  15. Wymann WE, Davis R, Patterson JW, Pfister JR (1988) Synth Commun 18:1379

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Science and Research Branch, Islamic Azad University, Ponak, Tehran, Iran

    Issa Yavari, Leila Azad & Tayebeh Sanaeishoar

Authors
  1. Issa Yavari
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Leila Azad
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tayebeh Sanaeishoar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Issa Yavari.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yavari, I., Azad, L. & Sanaeishoar, T. Synthesis of new functionalized alizarins from alizarin, acetylenic esters, and phosphorus nucleophiles. Monatsh Chem 142, 643–647 (2011). https://doi.org/10.1007/s00706-011-0489-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0489-3

Keywords

Search

Navigation