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Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles.
Odin, Ivan S; Chertov, Anton Yu; Grigor'eva, Olga B; Golovanov, Alexander A.
Afiliación
  • Odin IS; Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russia.
  • Chertov AY; Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russia.
  • Grigor'eva OB; Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russia.
  • Golovanov AA; Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russia.
J Org Chem ; 87(9): 5916-5924, 2022 05 06.
Article en En | MEDLINE | ID: mdl-35394780
ABSTRACT
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.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Acetileno / Alquinos Idioma: En Revista: J Org Chem Año: 2022 Tipo del documento: Article País de afiliación: Rusia

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Acetileno / Alquinos Idioma: En Revista: J Org Chem Año: 2022 Tipo del documento: Article País de afiliación: Rusia
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