Citation:
MUHAMMAD Naeem Ahmed, SHAHID Hameed, KHAWAJA Ansar Yasin, IFZAN Arshad, SAFEENA Zafar, MUHAMMAD Nawaz Tahir. Synthesis, Crystal Structure and Antimicrobial Activity of Ethyl 2-(1-cyclohexyl-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate[J]. Chinese Journal of Structural Chemistry,
2014, 33(11): 1666-1672.
doi:
10.14102/j.cnki.0254-5861.2011-0370
Synthesis, Crystal Structure and Antimicrobial Activity of Ethyl 2-(1-cyclohexyl-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate
摘要:
A novel 1,4,5-trisubstituted 1,2,3-triazole (C18H21N3O3) was synthesized by a one-pot three component reaction of 1-azidocyclohexane, 1-copper(Ⅰ) phenylethyne and ethoxalyl chloride at room temperature. The molecular structure was determined by single-crystal X-ray analysis. The compound crystallizes in the monoclinic system, space group P21/n with a=12.8167(9), b=8.0966(6), c=16.7079(9)Å, β=98.716(2)°, Z=4 and V=1713.8(2). In the crystal, the molecules are related by inversion and paired into dimers via C-H…O and C-O…C interactions involving (oxo) acetate groups. Furthermore, X-ray analysis results are compared with the optimized structure computed by using B3LYP method with 6-311G basis set. The calculated results showed that optimized geometry can well reproduce the crystal structure parameters. The bioassay results indicate that the compound has good antibacterial and antifungal activities.
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关键词:
- click chemistry
- / triazole
- / cyclohexyl
- / oxoacetate
- / XRD
- / antimicrobial
English
Synthesis, Crystal Structure and Antimicrobial Activity of Ethyl 2-(1-cyclohexyl-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate
Abstract:
A novel 1,4,5-trisubstituted 1,2,3-triazole (C18H21N3O3) was synthesized by a one-pot three component reaction of 1-azidocyclohexane, 1-copper(Ⅰ) phenylethyne and ethoxalyl chloride at room temperature. The molecular structure was determined by single-crystal X-ray analysis. The compound crystallizes in the monoclinic system, space group P21/n with a=12.8167(9), b=8.0966(6), c=16.7079(9)Å, β=98.716(2)°, Z=4 and V=1713.8(2). In the crystal, the molecules are related by inversion and paired into dimers via C-H…O and C-O…C interactions involving (oxo) acetate groups. Furthermore, X-ray analysis results are compared with the optimized structure computed by using B3LYP method with 6-311G basis set. The calculated results showed that optimized geometry can well reproduce the crystal structure parameters. The bioassay results indicate that the compound has good antibacterial and antifungal activities.
-
Key words:
- click chemistry
- / triazole
- / cyclohexyl
- / oxoacetate
- / XRD
- / antimicrobial
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