Nucleophilic addition of heterocyclic amines to conjugated enyne ketones

Голованов, А. А.; Bekin, V. V.; Odin, I. S.; Chertov, A. Yu.; Grigor’eva, O. B.; Pisareva, V. S.

doi:10.1134/s1070428015120039

Cited by 8 publications

(7 citation statements)

References 6 publications

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“…calcd for C 21 H 21 NO 2 : N 4.39, found: N 4.20. The substance is identical to a previously obtained product …”

Section: Experimental Sectionmentioning

confidence: 75%

“… a Rate constants of the pseudo-first-order reaction measured by a spectrophotometric method. b Earlier, the 4,5-adduct was obtained and characterized by us. c The 4,5-adduct portion increases; this makes spectrophotometric measurement difficult. d The reaction rate is very slow. …”

Section: Resultsmentioning

confidence: 99%

“…27,28 At the same time, the development of control methods for the relative activity of the electrophilic centers of similar polycentric Michael acceptors is a current problem. Previously, we revealed the reversibility of the 2,3-addition of cyclic amines 29 and thiophenols 30 solution. The reversibility of nucleophile addition by the carbon−carbon double bond allows us to examine the corresponding 2,3-adducts as the synthetic equivalents of conjugated 2,4,1-enynones in nucleophilic reactions.…”

Section: ■ Introductionmentioning

confidence: 99%

“…At the same time, the development of control methods for the relative activity of the electrophilic centers of similar polycentric Michael acceptors is a current problem. Previously, we revealed the reversibility of the 2,3-addition of cyclic amines and thiophenols to conjugated 2,4,1-enynones. The corresponding 2,3-adducts transform into stable 5-substituted penta-2,4-dien-1-ones (4,5-adducts of enynones) eventually or by heating the solution.…”

Section: Introductionmentioning

confidence: 99%

“…In consideration of the high rate (as compared with 4,5addition) and reversibility 29 of the 2,3-addition reaction of amine, we have to expect that 2,3-adducts of conjugated 2,4,1enynones possess quite good reactivity and selectivity of the interaction with nucleophiles by the propenone fragment.…”

Section: ■ Introductionmentioning

confidence: 99%

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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

et al. 2022

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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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“…calcd for C 21 H 21 NO 2 : N 4.39, found: N 4.20. The substance is identical to a previously obtained product …”

Section: Experimental Sectionmentioning

confidence: 75%