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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
ORIGINAL PAPER

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.

Keywords

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

Notes

Acknowledgment

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

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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

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