Skip to main content
SpringerLink
Log in

On the regioselectivity of the amberlyst-15 catalyzed condensation of 2-hydroxychalcones and 4,4-dimethylcyclohexane-1,3-dione

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

Abstract

Amberlyst-15 catalyzed condensation of 2-hydroxychalcones and 4,4-dimethylcyclohexane-1,3-dione in refluxing toluene was found to show regioselectivity resulting in (6R*,12S*)-2,2-dimethyl-6-phenyl-2,3,4,12-tetrahydro-1H-6,12-methanodibenzo[d,g][1,3]dioxocin-1-ones as the major product.

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
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Arnone A, Nasini G, Vajna de Pava O (1997) J Nat Prod 60:971

    Article  CAS  PubMed  Google Scholar 

  2. Kondo K, Kurihara M, Fukuhara K, Tanaka T, Suzuki T, Miyata N, Toyoda M (2000) Tetrahedron Lett 41:485

    Article  CAS  Google Scholar 

  3. Lou H, Yamazaki Y, Sasaki T, Uchida M, Tanaka H, Oka S (1999) Phytochemistry 51:297

    Article  CAS  Google Scholar 

  4. Ogundaini A, Farah M, Perera P, Samuelsson G, Bohlin L (1996) J Nat Prod 59:587

    Article  CAS  PubMed  Google Scholar 

  5. Xu X, Xie H, Wang Y, Wei X (2010) J Agric Food Chem 58:11667

    Article  CAS  PubMed  Google Scholar 

  6. Killday KB, Davey MH, Glinski JA, Duan P, Veluri R, Proni G, Daugherty FJ, Tempesta MS (2011) J Nat Prod 74:1833

    Article  CAS  PubMed  Google Scholar 

  7. Gallina L, Pozzo FD, Galligioni V, Bombardelli E, Scagliarini A (2011) Antiviral Res 92:447

    Article  CAS  PubMed  Google Scholar 

  8. Yang L-L, Chang C-C, Chen L-G, Wang C-C (2003) J Agric Food Chem 51:2974

    Article  CAS  PubMed  Google Scholar 

  9. Lin L-C, Kuo YC, Chou C-J (2002) J Nat Prod 65:505

    Article  CAS  PubMed  Google Scholar 

  10. Liu YZ, Cao YG, Ye JQ, Wang WG, Song KJ, Wanga XL, Wang CH, Li RT, Deng XM (2010) Fitoterapia 81:108

    Article  CAS  PubMed  Google Scholar 

  11. Yin G, Fan L, Ren T, Zheng C, Tao Q, Wub A, She N (2012) Org Biomol Chem 10:8877

    Article  CAS  PubMed  Google Scholar 

  12. Rao Y, Yin G (2013) Org Biomol Chem 11:6029

    Article  CAS  PubMed  Google Scholar 

  13. Yin G, Ren T, Rao Y, Zhou Y, Li Z, Shu W, Wu A (2013) J Org Chem 78:3132

    Article  CAS  PubMed  Google Scholar 

  14. Ganguly NC, Mondal P, Roy S (2013) Tetrahedron Lett 54:2386

    Article  CAS  Google Scholar 

  15. Xia L, Cai H, Lee YR (2014) Org Biomol Chem 12:4386

    Article  CAS  PubMed  Google Scholar 

  16. Reddy GM, Sridhar PR (2014) Eur J Org Chem 2014:1496

    Article  CAS  Google Scholar 

  17. Jiang X, Song Z, Xu C, Yao Q, Zhang A (2014) Eur J Org Chem 2014:418

    Article  CAS  Google Scholar 

  18. Bingi C, Emmadi NR, Chennapuram M, Nanubolu JB, Atmakur K (2014) RSC Adv 4:35009

    Article  CAS  Google Scholar 

  19. Guha C, Samanta S, Sepay N, Mallik AK (2015) Tetrahedron Lett 56:4954

    Article  CAS  Google Scholar 

  20. Samanta S, Sepay N, Mallik S, Mondal R, Molla MR, Mallik AK (2017) Synth Commun 47:2195

    Article  CAS  Google Scholar 

  21. Sepay N, Guha C, Maity S, Mallik AK (2017) Eur J Org Chem 2017:6013

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Financial support and spectral facilities from the PURSE and FIST programs of the DST and CAS program of the UGC, New Delhi to the Department of Chemistry, Jadavpur University are gratefully acknowledged. The UPE-II program of the UGC is also thanked for financial assistance. N.S., S.M., C.G. and R.M. are thankful to the UGC, New Delhi for their Research Fellowships.

Author information

Authors and Affiliations

  1. Department of Chemistry, Jadavpur University, Kolkata, 700032, India

    Nayim Sepay, Sumitava Mallik, Chayan Guha, Rina Mondal & Asok K. Mallik

Authors
  1. Nayim Sepay
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sumitava Mallik
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chayan Guha
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Rina Mondal
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Asok K. Mallik
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Asok K. Mallik.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 2779 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sepay, N., Mallik, S., Guha, C. et al. On the regioselectivity of the amberlyst-15 catalyzed condensation of 2-hydroxychalcones and 4,4-dimethylcyclohexane-1,3-dione. Monatsh Chem 149, 2113–2121 (2018). https://doi.org/10.1007/s00706-018-2258-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-018-2258-z

Keywords

Search

Navigation