期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 9, 页码 5916-5924出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00198
关键词
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The interaction between 1,5-diaryl-3-X-pent-4-yn-1-ones and arylhydrazines resulted in the synthesis of 3-aryl-5-arylethynyl-1-phenyl-4,5-dihydro-1H-pyrazoles with good yields. These compounds exhibited significant fluorescent abilities, with emission maximum wavelengths ranging from 453-465 nm and 363-400 nm.
An interaction of 1,5-diaryl-3-X-pent-4-yn-1-ones (where X stands for piperidin-1-yl, morpholin-4-yl, 4-methylpiperazin-1-yl) with arylhydrazines proceeds at room temperature and results in 3-aryl-5-arylethynyl-1-phenyl-4,5-dihydro-1H-pyrazoles with up to 57-73% yields. Under similar conditions, the cyclocondensation of conjugated 2,4,1-enynones with arylhydrazine proceeds only in the presence of cyclic amines. 1,5-Diaryl-3-X-pent-4-yn-1-ones are reported as synthetic equivalents of conjugated 2,4,1-enynones in reactions with arylhydrazines. On the basis of obtained data, there are highly efficient methods developed for the synthesis of 5-arylethynyl-substituted 4,5-dihydro-1H-pyrazoles, as well as for similarly structured 1H-pyrazoles prepared by oxidation in AcOH. Presented products possess quite marked fluorescent abilities. Emission maximum wavelengths are located at 453-465 and 363-400 nm, respectively; certain compounds show extremely large Stokes shifts that may reach 91,000 cm(-1).
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