Cyclization of arylhydrazones of cross-conjugated enynones: synthesis of luminescent styryl-1<i>H</i>-pyrazoles and propenyl-1<i>H</i>-pyrazoles

Itakhunov, Radik N; Odin, I. S.; Gusev, Dmitry M.; Grabovskii, S. A.; Gordon, Kareem V; Вологжанина, Анна В.; Sokov, S. A.; Sosnin, Ilya M.; Голованов, А. А.

doi:10.1039/d2ob01427k

Cited by 5 publications

(14 citation statements)

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“…This fact correlated with data about the influence of medium acidity on the direction of similar reactions. 8a c Actually, it was confirmed by our own negative experience (poor repeatability of results in pre-experiments). Therefore, used solvents require accurate purification from the traces of acids and bases.…”

Section: Table 1 Interaction Of Enynone 1...mentioning

confidence: 68%

“…9 Besides, biological activity is not the only practical ability of pyrazole structural fragment. There are novel photochromic materials, 10 liquid crystals, 11 and fluorescent probes 8c 12 revealed in the observing range of heterocycles. Strictly speaking, even a brief analysis of literature data demonstrates that one of the primary research branches of the chemistry of heterocyclic compounds is still the exploring of synthetic uses of 1,2-azoles.…”

Section: Table 1 Interaction Of Enynone 1...mentioning

confidence: 99%

“…Polyfunctionality of cross-conjugated enynones as Michael acceptors allows to obtain isomeric 3- and 5-ethenylpyrazoles, 8a c 3-alkynyl-4,5-dihydro-1 H -pyrazoles, 21b 28b and arylhydrazones 8c as a result of their interactions with hydrazines. Due to the different chemical nature of three electrophilic centers (β-carbons of multiple bonds and a carbonyl group carbon atom), the pointed reactions proceed in high chemoselectivity.…”

Section: Table 1 Interaction Of Enynone 1...mentioning

confidence: 99%

“…For determining conditions of the 3-alkynylpyrazolines selective synthesis, we have examined interactions of easily available 8c 14 34 enynones 1 with a wide variety of monosubstituted hydrazines 2 (Figure 2 ).…”

Section: Table 1 Interaction Of Enynone 1...mentioning

confidence: 99%

“…f Here, the isomer of compound 7 , ( E )-1-phenyl-5-(2-phenylethenyl)-1 H -pyrazole ( 8 ) was formed (in 87% yield). 8c…”

Section: Table 1 Interaction Of Enynone 1...mentioning

confidence: 99%

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Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs

Golovanov,

Odin,

Gordon

et al. 2023

Synthesis

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On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me3Si, Et3Si, and t-BuMe2Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.

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Section: Table 1 Interaction Of Enynone 1...mentioning

confidence: 68%

Section: Table 1 Interaction Of Enynone 1...mentioning

confidence: 99%