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Updated: May 15, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
1-[1-(2,1,3-Benzoxadiazol-5-ylmeth-yl)-1H-1,2,3-triazol-4-yl]hexan-1-one
Jessie A Key1, Christopher W Cairo, Robert McDonald
1Alberta Glycomics Centre, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.
Abstract:
The title compound, C(15)H(17)N(5)O(2), was synthesized as part of a series of benzoxadiazole analogs which were examined for fluorescent properties by Cu-catalysed azide-alkyne cyclo-addition (CuAAC) of a 4-azido-methyl-benzoxadiazole substrate. The structure shows a nearly coplanar orientation of the hexa-none keto group and the 1,2,3-triazole ring [dihedral angle = 4.3 (3)°], while the benzoxadiazole and triazole groups are much more severely inclined [dihedral angle = 70.87 (4)°]. In the crystal, weak C-H⋯N inter-actions connect translationally-related triazole rings, while another set of C-H⋯N inter-actions is formed between inversion-related benzoxadiazole units, forming a three-dimensional network. The crystal studied was a non-merohedral twin with refined value of the twin fraction of 0.2289 (16).
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