Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles.
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.
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01-internacional
Base de datos:
MEDLINE
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Acetileno
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En
Revista:
J Org Chem
Año:
2022
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Article
País de afiliación:
Rusia