Skip to main content
SpringerLink
Log in

An Efficient and Simple One-Pot Synthesis of Novel 2-Amino-5-aza-6-(dinitrilomethylene)-4,7,7-trimethylbicyclo[2.2.2]octane-1,3-dicarbo-nitrile and its Crystal Structure

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The title compound was prepared by the reaction of 4-methyl-pent-3-en-2-one and malononitrile, at room temperature, in the presence of indium-triflate and triethylamine. The structure of the molecule was established by spectral analysis and X-ray diffraction studies. The compound crystallizes in the monoclinic space group C2/c with unit cell parameters: a = 14.269 (2), b = 10.141 (2), c = 19.743 (3) Å, β = 95.523(4)°, Z = 8. The crystal structure was solved by direct methods and refined to R = 0.0526 for 2,690 observed reflections. The isoquinuclidine rings adopt boat conformation. The molecules in the unit cell are arranged in layers. The crystal structure is stabilized by N–H⋯N interactions.

Graphical Abstract

Crystal structure analysis of the novel 2-amino-5-aza-6-(dinitrilomethylene)-4,7,7-trimethylbicyclo[2.2.2]octane-1,3-dicarbonitrile.

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
Scheme 1
Fig. 2

Similar content being viewed by others

References

  1. O’Hagan D (2000) Nat Prod Rep 17:435

    Article  Google Scholar 

  2. Weiland H, Schopf C, Hermsen W (1925) Liebigs Ann Chem 444:40

    Article  Google Scholar 

  3. Kanistan HU, Garner P (2007) J Am Chem Soc 129:15460

    Article  Google Scholar 

  4. Cereda E, Ezhaya A, Gil QM, Bellora E, Dubini E, Micheletti R, Shiavone A, Brambilla A, Shiavi GB, Donetti A (1990) J Med Chem 33:2108

    Article  CAS  Google Scholar 

  5. Godovickov NN, Dorofeeva NA, Kardanov NA, Trifonova SA, Shelkovnikov SA (1985) Khim Farm Zh 19:1060

    Google Scholar 

  6. Tropsha AE, Nizhnii SV, Iaguzhinskii LS (1985) Bioorg Khim 11:1402

    CAS  Google Scholar 

  7. Rzeszotarski WJ, McPherson DW, Ferkany JW, Kinnier WJ, Naronha-Blob L, Rzeszotarski AK (1998) J Med Chem 31:1463

    Article  Google Scholar 

  8. Kiesewetter DO, Silverton JV, Eckelman WC (1995) J Med Chem 38:1711

    Article  CAS  Google Scholar 

  9. Martel AM, Rabasseda X, Castaner J (1997) Drugs Future 22:135

    CAS  Google Scholar 

  10. Gross NJ (2006) Eur J Pharmacol 533:36

    Article  CAS  Google Scholar 

  11. MacLeeod AM, Merchants KJ, Shewell GA, Saunders J, Herbert RH, Freedman SB, Harley EA (1990) J Med Chem 33:2690

    Article  Google Scholar 

  12. Sunden H, Ibrahem H, Erickson L, Cordova A (2005) Angew Chem Int Ed 44:4877

    Article  CAS  Google Scholar 

  13. Liu H, Cun L-F, Mi A-Q, Jiang Y-Z, Gong L-Z (2006) Org Lett 8:6023

    Article  CAS  Google Scholar 

  14. Rueoing M, Azap C (2005) Angew Chem Int Ed 44:7832

    Article  Google Scholar 

  15. Sheldrick GM (1997) SHELXS97 and SHELXL97. University of Gottingen, Gottingen

    Google Scholar 

  16. Farrugia LJ (1997) J Appl Crystallogr 30:565

    Article  CAS  Google Scholar 

  17. Kumar S, Kaur P, Kumar V (2005) Curr Org Chem 9:1205

    Article  CAS  Google Scholar 

  18. Fringuilli F, Piermatti O, Pizzo F, Voccaro L (2003) Curr Org Chem 7:1661

    Article  Google Scholar 

  19. Zhang Y, Li P, Wang M (2009) J Org Chem 74:4364

    Article  CAS  Google Scholar 

  20. Vencato I, Mascarenhas YP, Braz FR (1987) Acta Crystallogr C43:762

    CAS  Google Scholar 

  21. Moisan L, Doris E, Rousseau B, Thuery P (2004) Acta Crystallogr C60:792

    Google Scholar 

  22. Zhang XM, Lu JT (2007) Acta Crystallogr E63:3861

    Google Scholar 

  23. Duax WL, Norton DA (1975) Atlas of steroid structures, vol 1. Plenum, New York

    Google Scholar 

Download references

Acknowledgments

The authors are thankful to Prof. P. K. Bharadwaj, Department of Chemistry, IIT, Kanpur, India, for the use of the data collection facility.

Author information

Authors and Affiliations

  1. P.G. Department of Chemistry, University of Jammu, Jammu Tawi, 180 006, India

    Nitu Mahajan & T. K. Razdan

  2. P.G. Department of Physics, University of Jammu, Jammu Tawi, 180 006, India

    Vivek K. Gupta & Pinki Kotwal

  3. Department of Chemistry, Guru Nanak Dev University, Amritsar, India

    Ajay P. S. Pannu

Authors
  1. Nitu Mahajan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vivek K. Gupta
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pinki Kotwal
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ajay P. S. Pannu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. T. K. Razdan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vivek K. Gupta.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mahajan, N., Gupta, V.K., Kotwal, P. et al. An Efficient and Simple One-Pot Synthesis of Novel 2-Amino-5-aza-6-(dinitrilomethylene)-4,7,7-trimethylbicyclo[2.2.2]octane-1,3-dicarbo-nitrile and its Crystal Structure. J Chem Crystallogr 41, 552–556 (2011). https://doi.org/10.1007/s10870-010-9919-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-010-9919-z

Keywords

Search

Navigation