Citation:
MUHAMMAD Naeem Ahmed, KHAWAJA Ansar Yasin, MUHAMMAD Nawaz Tahir, IFZAN Arshad, MURTAZA Madni. One-pot Synthesis, Crystal Structures and Antimicrobial Activities of Two New 1,4-Disubstituted 1,2,3-Triazole-4-Carboxylates[J]. Chinese Journal of Structural Chemistry,
2015, 34(1): 26-32.
doi:
10.14102/j.cnki.0254-5861.2011-0457
One-pot Synthesis, Crystal Structures and Antimicrobial Activities of Two New 1,4-Disubstituted 1,2,3-Triazole-4-Carboxylates
摘要:
Two new 1,4-disubstituted 1,2,3-triazoles-4-carboxylates were synthesized via click reaction. Compound 1a was synthesized by the interaction of 6-nitro-tetrazolo[1.5-a]-pyridine with ethyl propynoate at room temperature in the presence of Cu(OAc)2 as a catalyst and THF as solvent. Compound 1b was also synthesized by the same manner except that tert-butyl propionate, instead of ethyl propynoate, was used. The compounds were characterized by IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction analysis. Compound 1a (C10H9N5O4) crystallizes in the triclinic system, space group P1 with a=5.0894(9), b=8.9834(13), c=13.089(2)Å, α=83.041(7), β=80.256(7), γ=87.296(8)°, V=585.24(16)Å3, Z=2, Mr=263.22, crystal size (mm)=0.37×0.20×0.18, (I>2σ(I))=8557, 2493, 1229, Rint=0.057. Compound 1b (C12H13N5O4) crystallizes in the monoclinic system, space group P21/c with a=6.8854(5), b=21.783(2), c=9.3986(8)Å, β=93.239(4)°, V=1407.4(2)Å3, Z=4, Mr=291.27, crystal size (mm)=0.38×0.22×0.20, (I>2σ(I))=11842, 3172, 1866, Rint=0.047. Antimicrobial assay results showed that the title compounds display excellent activities to different bacterial and fungal strains.
English
One-pot Synthesis, Crystal Structures and Antimicrobial Activities of Two New 1,4-Disubstituted 1,2,3-Triazole-4-Carboxylates
Abstract:
Two new 1,4-disubstituted 1,2,3-triazoles-4-carboxylates were synthesized via click reaction. Compound 1a was synthesized by the interaction of 6-nitro-tetrazolo[1.5-a]-pyridine with ethyl propynoate at room temperature in the presence of Cu(OAc)2 as a catalyst and THF as solvent. Compound 1b was also synthesized by the same manner except that tert-butyl propionate, instead of ethyl propynoate, was used. The compounds were characterized by IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction analysis. Compound 1a (C10H9N5O4) crystallizes in the triclinic system, space group P1 with a=5.0894(9), b=8.9834(13), c=13.089(2)Å, α=83.041(7), β=80.256(7), γ=87.296(8)°, V=585.24(16)Å3, Z=2, Mr=263.22, crystal size (mm)=0.37×0.20×0.18, (I>2σ(I))=8557, 2493, 1229, Rint=0.057. Compound 1b (C12H13N5O4) crystallizes in the monoclinic system, space group P21/c with a=6.8854(5), b=21.783(2), c=9.3986(8)Å, β=93.239(4)°, V=1407.4(2)Å3, Z=4, Mr=291.27, crystal size (mm)=0.38×0.22×0.20, (I>2σ(I))=11842, 3172, 1866, Rint=0.047. Antimicrobial assay results showed that the title compounds display excellent activities to different bacterial and fungal strains.
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Key words:
- click reaction
- / triazoles
- / crystal structure
- / antimicrobial activity
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