Journal of Chemical Crystallography

, Volume 41, Issue 3, pp 316–321 | Cite as

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

  • He-Xiang Bai
  • Jing-Mei Wang
  • Shi-Jing Xia
  • Quan-Rui Wang


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.


1,2,4-Triazole Azepine 3-Aza-A-Homocholestane Synthesis Crystal Structure 



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


  1. 1.
    Garratt PJ (1996) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive HeterocyclicChemistry II, vol 4. Pergamon Press, Oxford, p 127Google Scholar
  2. 2.
    Turnbull K (1998) Prog Heterocycl Chem 10:153CrossRefGoogle Scholar
  3. 3.
    Al-Masoudi IA, Al-Souda YA, Al-Salihi NJ, Al-Masoudi NA (2006) Khim Geterotsikl Soedin 11:1605Google Scholar
  4. 4.
    Terrell CL (1999) Mayo Clin Proc 74:78CrossRefGoogle Scholar
  5. 5.
    Koltin Y, Hitchcock CA (1997) Curr Opin Chem Biol 1:176CrossRefGoogle Scholar
  6. 6.
    Staben ST, Blaquiere N (2010) Angew Chem Int Ed Engl 49:325Google Scholar
  7. 7.
    Girgis AS, Barsoum FF (2009) Eur J Med Chem 44:1972CrossRefGoogle Scholar
  8. 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 47:101CrossRefGoogle Scholar
  9. 9.
    Broggini G, Garanti L, Molteni G, Zecchi G (1995) Synthesis 1483Google Scholar
  10. 10.
    Al-Soud YA, Qalalweh MNA, Al-Sa’doni HH, Al-Masoudi NA (2005) Heteroatom Chem 16:28CrossRefGoogle Scholar
  11. 11.
    Kwon T, Heiman ASE, Oriaku T, Yoon KH, Lee J (1995) J Med Chem 38:1048CrossRefGoogle Scholar
  12. 12.
    Elmegeed GA, Wardakhan WW, Younis M, Louca NA (2004) Arch Pharm Pharm Med Chem 337:140CrossRefGoogle Scholar
  13. 13.
    Abdelhamid AO, Abdelhalim MM, Elmegeed GA (2007) J Heterocyclic Chem 44:7CrossRefGoogle Scholar
  14. 14.
    Burbiel J, Bracher F (2003) Steroids 68:587CrossRefGoogle Scholar
  15. 15.
    Elmegeed GA, Wardakhan WW, Baiuomy AR (2005) Pharmazie 60:328Google Scholar
  16. 16.
    Ahmad MS, Alam Z (1988) Indian J Chem Sect B: Org Chem Include Med Chem 27B:1001Google Scholar
  17. 17.
    Mushfiq M, Iqbal N (1986) J Chem Res-S 254Google Scholar
  18. 18.
    Elmegeed GA, Wardakhan WW, Younis M, Louca NA (2004) Arch Pharm 337:140CrossRefGoogle Scholar
  19. 19.
    Desai P, Schildknegt K, Agrios KA, Mossman C, Milligan GL, Aube J (2000) J Am Chem Soc 122:7226CrossRefGoogle Scholar
  20. 20.
    Ahmad MS, Alam Z (1988) Indian J Chem Sect B: Org Chem Include Med Chem 27B:336Google Scholar
  21. 21.
    Craig JC, Naik AR (1962) J Am Chem Soc 84:3410CrossRefGoogle Scholar
  22. 22.
    Doorenbos NJ, Wu MT (1961) J Org Chem 26:2548CrossRefGoogle Scholar
  23. 23.
    Meng QQ, Bai HX, Wang QR, Tao FG (2007) Synthesis 33Google Scholar
  24. 24.
    Wang QR, Liu XJ, Li F, Ding ZB, Tao FG (2002) Synth Commun 32:1327CrossRefGoogle Scholar
  25. 25.
    Wang QR, Li Z, Yang HY, Li F, Ding ZB, Tao FG (2003) Synthesis 1231Google Scholar
  26. 26.
    Sheldrick GM (1997) SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen, GermanyGoogle Scholar
  27. 27.
    Hasan M, Rashid N, Khan KM, Snatzke G, Duddeck H, Voelter W (1995) Liebigs Ann 889Google Scholar
  28. 28.
    Brown FJ, Djerassi C (1980) J Am Chem Soc 102:807CrossRefGoogle Scholar
  29. 29.
    Wang QR, Jochims JC, Kohlbrandt S, Dalenburg L, Al-Talib M, Hamed IAE (1992) Synthesis 710Google Scholar
  30. 30.
    Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans II:S1Google Scholar
  31. 31.
    Song XJ, Tan XH, Wang YG (2008) J Chem Crystallogr 38:478Google Scholar
  32. 32.
    Schantl JG, Rettenbacher AS, Wurst K (1998) Angew Chem Int Ed Engl 37:2229CrossRefGoogle Scholar
  33. 33.
    Dewar MJS, Thiel W (1977) J Am Chem Soc 99:4907CrossRefGoogle Scholar
  34. 34.
    Liu XJ, Liu Y, Ding ZB, Wang QR, Zhang CZ (2000) J Heterocyclic Chem 37:287Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • He-Xiang Bai
    • 1
  • Jing-Mei Wang
    • 1
  • Shi-Jing Xia
    • 1
  • Quan-Rui Wang
    • 1
  1. 1.Department of ChemistryFudan UniversityShanghaiPeople’s Republic of China

Personalised recommendations