Skip to main content
SpringerLink
Log in

Synthesis and Crystal Structure of [1,2,4]-Triazolo-annulated 3-Aza-A-homocholestane Derivative: A Novel Pentaheterocyclic Ring System

  • ORIGINAL PAPER
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

A novel pentaheterocyclic ring system derived from (5α)-cholestan-3-one, i.e. [1R-[1α(R*),3aβ,3bα,5aβ,12aα,12bβ,14aα]]-1-(1,5-dimethylhexyl)-1,2,3,3a,3b,4,5,11,12,12a,12b,13,14,14a-tetradecahydro-8,12a,14a-trimethyl-9-(2,4,6-trichlorophenyl)-cyclopenta[5,6]naphtho[2,1-d][1,2,4]triazolo[1,5-a]azepinium hexachloroantimonate (6) has been synthesized via the reverse-electron-demand 1,3-dipolar cycloaddition of the 1-aza-2-azoniaallene cation 4 to the triple bond of acetonitrile followed by ring enlargement. The structure of 6 was determined by NMR, IR and high-resolution mass spectra, and unequivocally confirmed by X-ray crystallographic analysis. The title compound crystallizes in monoclinic class under the space group P2-1 with a = 8.163(3) Å, b = 11.214(4) Å, c = 24.191(9) Å, α = 90°, β = 97.740(5)°, and γ = 90°. The five-membered triazole ring is essentially planar and aromatic, while the seven-membered azepine ring is not planar, but adopts a chair-like conformation.

Graphical Abstract

[1R-[1α(R*),3aβ,3bα,5aβ,12aα,12bβ,14aα]]-1-(1,5-dimethylhexyl)-1,2,3,3a,3b,4,5,11,12,12a,12b,13,14,14a-tetradecahydro-8,12a,14a-trimethyl-9-(2,4,6-trichlorophenyl)-cyclopenta[5,6]naphtho[2,1-d][1,2,4]triazolo[1,5-a]azepinium hexachloroantimonate (6) has been synthesized and unequivocally confirmed by X-ray crystallographic analysis.

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
Fig. 1
Fig. 2

Similar content being viewed by others

Notes

  1. For comparison of the metric parameters with a 1H-1,2,4-triazolo[3,2-d][1,5]-benzoxaepinum salt investigated previously by us [34].

References

  1. Garratt PJ (1996) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive HeterocyclicChemistry II, vol 4. Pergamon Press, Oxford, p 127

  2. Turnbull K (1998) Prog Heterocycl Chem 10:153

    Article  CAS  Google Scholar 

  3. Al-Masoudi IA, Al-Souda YA, Al-Salihi NJ, Al-Masoudi NA (2006) Khim Geterotsikl Soedin 11:1605

    Google Scholar 

  4. Terrell CL (1999) Mayo Clin Proc 74:78

    Article  CAS  Google Scholar 

  5. Koltin Y, Hitchcock CA (1997) Curr Opin Chem Biol 1:176

    Article  CAS  Google Scholar 

  6. Staben ST, Blaquiere N (2010) Angew Chem Int Ed Engl 49:325

    CAS  Google Scholar 

  7. Girgis AS, Barsoum FF (2009) Eur J Med Chem 44:1972

    Article  CAS  Google Scholar 

  8. Cho H, Murakami K, Nakanishi H, Fujisawa AK, Isoshima H, Niwa M, Hayakawa K, Hase Y, Uchida I, Watanabe H, Wakitani K, Aisaka K (2004) J Med Chem 47:101

    Article  CAS  Google Scholar 

  9. Broggini G, Garanti L, Molteni G, Zecchi G (1995) Synthesis 1483

  10. Al-Soud YA, Qalalweh MNA, Al-Sa’doni HH, Al-Masoudi NA (2005) Heteroatom Chem 16:28

    Article  CAS  Google Scholar 

  11. Kwon T, Heiman ASE, Oriaku T, Yoon KH, Lee J (1995) J Med Chem 38:1048

    Article  CAS  Google Scholar 

  12. Elmegeed GA, Wardakhan WW, Younis M, Louca NA (2004) Arch Pharm Pharm Med Chem 337:140

    Article  CAS  Google Scholar 

  13. Abdelhamid AO, Abdelhalim MM, Elmegeed GA (2007) J Heterocyclic Chem 44:7

    Article  CAS  Google Scholar 

  14. Burbiel J, Bracher F (2003) Steroids 68:587

    Article  CAS  Google Scholar 

  15. Elmegeed GA, Wardakhan WW, Baiuomy AR (2005) Pharmazie 60:328

    CAS  Google Scholar 

  16. Ahmad MS, Alam Z (1988) Indian J Chem Sect B: Org Chem Include Med Chem 27B:1001

    CAS  Google Scholar 

  17. Mushfiq M, Iqbal N (1986) J Chem Res-S 254

  18. Elmegeed GA, Wardakhan WW, Younis M, Louca NA (2004) Arch Pharm 337:140

    Article  CAS  Google Scholar 

  19. Desai P, Schildknegt K, Agrios KA, Mossman C, Milligan GL, Aube J (2000) J Am Chem Soc 122:7226

    Article  CAS  Google Scholar 

  20. Ahmad MS, Alam Z (1988) Indian J Chem Sect B: Org Chem Include Med Chem 27B:336

    CAS  Google Scholar 

  21. Craig JC, Naik AR (1962) J Am Chem Soc 84:3410

    Article  CAS  Google Scholar 

  22. Doorenbos NJ, Wu MT (1961) J Org Chem 26:2548

    Article  CAS  Google Scholar 

  23. Meng QQ, Bai HX, Wang QR, Tao FG (2007) Synthesis 33

  24. Wang QR, Liu XJ, Li F, Ding ZB, Tao FG (2002) Synth Commun 32:1327

    Article  CAS  Google Scholar 

  25. Wang QR, Li Z, Yang HY, Li F, Ding ZB, Tao FG (2003) Synthesis 1231

  26. Sheldrick GM (1997) SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen, Germany

  27. Hasan M, Rashid N, Khan KM, Snatzke G, Duddeck H, Voelter W (1995) Liebigs Ann 889

  28. Brown FJ, Djerassi C (1980) J Am Chem Soc 102:807

    Article  CAS  Google Scholar 

  29. Wang QR, Jochims JC, Kohlbrandt S, Dalenburg L, Al-Talib M, Hamed IAE (1992) Synthesis 710

  30. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans II:S1

  31. Song XJ, Tan XH, Wang YG (2008) J Chem Crystallogr 38:478

    Google Scholar 

  32. Schantl JG, Rettenbacher AS, Wurst K (1998) Angew Chem Int Ed Engl 37:2229

    Article  CAS  Google Scholar 

  33. Dewar MJS, Thiel W (1977) J Am Chem Soc 99:4907

    Article  CAS  Google Scholar 

  34. Liu XJ, Liu Y, Ding ZB, Wang QR, Zhang CZ (2000) J Heterocyclic Chem 37:287

    Google Scholar 

Download references

Acknowledgment

This study was carried out with the financial assistance of the National Natural Science Foundation of China (Project 20372015).

Author information

Authors and Affiliations

  1. Department of Chemistry, Fudan University, Shanghai, 200433, People’s Republic of China

    He-Xiang Bai, Jing-Mei Wang, Shi-Jing Xia & Quan-Rui Wang

Authors
  1. He-Xiang Bai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jing-Mei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shi-Jing Xia
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Quan-Rui Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Quan-Rui Wang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bai, HX., Wang, JM., Xia, SJ. et al. Synthesis and Crystal Structure of [1,2,4]-Triazolo-annulated 3-Aza-A-homocholestane Derivative: A Novel Pentaheterocyclic Ring System. J Chem Crystallogr 41, 316–321 (2011). https://doi.org/10.1007/s10870-010-9880-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-010-9880-x

Keywords

Search

Navigation