Cu(I)-catalyzed alkyne-azide "click' cycloaddition (CuAAC): a clean, efficient, and mild synthesis of new 1,4-disubstituted 1H-1,2,3-triazole-linked 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile-crystal structure

被引:15
|
作者
Aghbash, Khadijeh Ojaghi [1 ]
Pesyan, Nader Noroozi [1 ]
Sahin, Ertan [2 ]
机构
[1] Urmia Univ, Dept Organ Chem, Fac Chem, Orumiyeh 57159, Iran
[2] Ataturk Univ, Fac Sci, Dept Chem, TR-25240 Erzurum, Turkey
关键词
4H-pyrans; 2-Amino-6-(azidomethyl)-4; 8-dihydropyrano[3; 2-b]pyran-3-carbonitrile; Azide-alkyne; 1; 3-dipolar cycloaddition; Click reaction; Copper catalysis; 1,2,3-Triazoles; Dimeric form; Co-crystal; THROUGHPUT SCREENING ASSAY; ONE-POT SYNTHESIS; APOPTOSIS INDUCERS; ANTIBACTERIAL ACTIVITY; 1,2,3-TRIAZOLE DERIVATIVES; GREEN SYNTHESIS; DISCOVERY; SERIES; 4-ARYL-4H-CHROMENES; CHEMISTRY;
D O I
10.1007/s11164-018-03723-x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cu(I)-catalyzed alkyne-azide click' cycloaddition (CuAAC) is an important click chemistry'' reaction that is widely known in materials science, chemical biology, and pharmaceutical chemistry. The CuAAC reaction of terminal alkynes affords an efficient and mild production of triazolic 1,4-disubstituted compounds. In this work, a green and valuable method was introduced for the synthesis of the category of different new 1,4-disubstituted 1,2,3-triazole swapped with a 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-cyano moiety. These triazolic derivatives were produced by treatment of various 2-amino-6-(azidomethyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles with phenylacetylene in the presence of CuI as a catalyst with excellent yields (because CuAAC is selective to 1,4-disubstituted triazole derivatives) in a green solvent (ethanol/water). All structures were evaluated by C-13, H-1 NMR, and FT-IR spectroscopy and a compound was analyzed by crystallography (X-ray) technique.
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页码:2079 / 2094
页数:16
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