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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 2113–2121 | Cite as

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

  • Nayim Sepay
  • Sumitava Mallik
  • Chayan Guha
  • Rina Mondal
  • Asok K. Mallik
Original Paper
  • 86 Downloads

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

Keywords

2-Hydroxychalcones 4,4-Dimethylcyclohexane-1,3-dione Amberlyst-15 Regioselective condensation (6R*,12S*)-2,2-Dimethyl-6-phenyl-2,3,4,12-tetrahydro-1H-6,12-methanodibenzo[d,g][1,3]dioxocin-1-ones 

Notes

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.

Supplementary material

706_2018_2258_MOESM1_ESM.pdf (2.7 mb)
Supplementary material 1 (PDF 2779 kb)

References

  1. 1.
    Arnone A, Nasini G, Vajna de Pava O (1997) J Nat Prod 60:971CrossRefPubMedGoogle Scholar
  2. 2.
    Kondo K, Kurihara M, Fukuhara K, Tanaka T, Suzuki T, Miyata N, Toyoda M (2000) Tetrahedron Lett 41:485CrossRefGoogle Scholar
  3. 3.
    Lou H, Yamazaki Y, Sasaki T, Uchida M, Tanaka H, Oka S (1999) Phytochemistry 51:297CrossRefGoogle Scholar
  4. 4.
    Ogundaini A, Farah M, Perera P, Samuelsson G, Bohlin L (1996) J Nat Prod 59:587CrossRefPubMedGoogle Scholar
  5. 5.
    Xu X, Xie H, Wang Y, Wei X (2010) J Agric Food Chem 58:11667CrossRefPubMedGoogle Scholar
  6. 6.
    Killday KB, Davey MH, Glinski JA, Duan P, Veluri R, Proni G, Daugherty FJ, Tempesta MS (2011) J Nat Prod 74:1833CrossRefPubMedGoogle Scholar
  7. 7.
    Gallina L, Pozzo FD, Galligioni V, Bombardelli E, Scagliarini A (2011) Antiviral Res 92:447CrossRefPubMedGoogle Scholar
  8. 8.
    Yang L-L, Chang C-C, Chen L-G, Wang C-C (2003) J Agric Food Chem 51:2974CrossRefPubMedGoogle Scholar
  9. 9.
    Lin L-C, Kuo YC, Chou C-J (2002) J Nat Prod 65:505CrossRefPubMedGoogle Scholar
  10. 10.
    Liu YZ, Cao YG, Ye JQ, Wang WG, Song KJ, Wanga XL, Wang CH, Li RT, Deng XM (2010) Fitoterapia 81:108CrossRefPubMedGoogle Scholar
  11. 11.
    Yin G, Fan L, Ren T, Zheng C, Tao Q, Wub A, She N (2012) Org Biomol Chem 10:8877CrossRefPubMedGoogle Scholar
  12. 12.
    Rao Y, Yin G (2013) Org Biomol Chem 11:6029CrossRefPubMedGoogle Scholar
  13. 13.
    Yin G, Ren T, Rao Y, Zhou Y, Li Z, Shu W, Wu A (2013) J Org Chem 78:3132CrossRefPubMedGoogle Scholar
  14. 14.
    Ganguly NC, Mondal P, Roy S (2013) Tetrahedron Lett 54:2386CrossRefGoogle Scholar
  15. 15.
    Xia L, Cai H, Lee YR (2014) Org Biomol Chem 12:4386CrossRefPubMedGoogle Scholar
  16. 16.
    Reddy GM, Sridhar PR (2014) Eur J Org Chem 2014:1496CrossRefGoogle Scholar
  17. 17.
    Jiang X, Song Z, Xu C, Yao Q, Zhang A (2014) Eur J Org Chem 2014:418CrossRefGoogle Scholar
  18. 18.
    Bingi C, Emmadi NR, Chennapuram M, Nanubolu JB, Atmakur K (2014) RSC Adv 4:35009CrossRefGoogle Scholar
  19. 19.
    Guha C, Samanta S, Sepay N, Mallik AK (2015) Tetrahedron Lett 56:4954CrossRefGoogle Scholar
  20. 20.
    Samanta S, Sepay N, Mallik S, Mondal R, Molla MR, Mallik AK (2017) Synth Commun 47:2195CrossRefGoogle Scholar
  21. 21.
    Sepay N, Guha C, Maity S, Mallik AK (2017) Eur J Org Chem 2017:6013CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Nayim Sepay
    • 1
  • Sumitava Mallik
    • 1
  • Chayan Guha
    • 1
  • Rina Mondal
    • 1
  • Asok K. Mallik
    • 1
  1. 1.Department of ChemistryJadavpur UniversityKolkataIndia

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