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Updated: May 15, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
Jessie A Key1, Christopher W Cairo, Michael J Ferguson
1Alberta Glycomics Centre, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.
Abstract:
The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catal-ysed azide-alkyne cyclo-addition (CuAAC) from the corres-ponding n-octyne and 4-azido-benzoxadiazole. The benz-oxa-diazole and triazole rings show a roughly planar orientation [dihedral angle between the ring planes = 12.18 (5)°]. The alkane chain adopts a zigzag conformation, which deviates from the central triazole ring by 20.89 (6)°. These two torsion angles result in an overall twist to the structure, with a dihedral angle of 32.86 (7)° between the benzoxadiazole group and the hexyl chain. The crystal structure features C-H⋯N hydrogen bonds leading to chains propagating along [2-10] and offset parallel stacking inter-actions of the triazole and benzoxadiazole rings. The centroid of the extended π-system formed by the benzoxadiazole and triazole rings (14 atoms total) was calculated; the centroid-centroid distance was 4.179 Å, interplanar separation was 3.243 Å, and the resulting offset was 2.636 Å.
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