Domino reactions of vinyl ethynyl ketones with 1-aryl-3,4-dihydroisoquinolines — Search for selectivity

Matveeva, Maria D.; Голованов, А. А.; Борисова, Т. Н.; Титов, А. А.; Варламов, А. В.; Shaabani, Ahmad; Obydennik, Arina Y.; Voskressensky, Leonid G.

doi:10.1016/j.mcat.2018.09.020

Cited by 17 publications

(3 citation statements)

References 30 publications

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“…The object of this work was to discover conditions providing the direct synthesis of alkenyl-substituted pyrazoles which will increase the synthetic potential of cross-conjugated enynones. It is necessary to admit that recently the possibility of the selective implication of the synthesis of the double or triple bond of 1,5-disubstituted pent-1-en-4-yn-3-ones into the pyrrolo[2,1-α]isoquinolines was demonstrated successfully …”

Section: Introductionmentioning

confidence: 99%

Reactivity of Cross-Conjugated Enynones in Cyclocondensations with Hydrazines: Synthesis of Pyrazoles and Pyrazolines

et al. 2021

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The cyclocondensation of cross-conjugated enynones, dienynones, and trienynones (easily available due to low-cost starting compounds) with arylhydrazines leads to the regioselective synthesis of pyrazole derivatives (dihetaryl-substituted ethens, buta-1,3-diens, and hexa-1,3,5-triens) or results in 4,5-dihydro-1H-pyrazoles in good yield. The reaction path is controlled by the character of the substituent in enynone: the pyrazoles are obtained from the reaction of substrates that contain five-membered heteroaromatic substituents with arylhydrazines, and the 4,5-dihydro-1H-pyrazoles are obtained from the reaction of 1,5-diphenylpent-1-en-4-yn-3-one with arylhydrazines consistently. Despite the presence of a substituent, cyclocondensation of 2-hydrazinylpyridine with all of examined cross-conjugated enynones leads to the formation of pyrazoles. The reaction does not require special conditions (temperature, catalyst, inert atmosphere). The cyclocondensation pathways are determined by the electronic effect of an electron-rich five-membered heteroaromatic ring in the substrate. The synthesis allows use of various substituents and functional groups in enynone and hydrazine. The present method features high yields and simplicity of the product purification. The obtained pyrazoles possess fluorescent properties with a quantum yield up to 31%.

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Section: Introductionmentioning

confidence: 99%

Reactivity of Cross-Conjugated Enynones in Cyclocondensations with Hydrazines: Synthesis of Pyrazoles and Pyrazolines

et al. 2021

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“…Subsequently, Voskressensky et al used the same catalyst for the cycloaddition of 1-aroyl-3,4-dihydroisoquinoline and ynones. 478 Following the former approach (Scheme 265), the click reaction of alkynes (48a), alkyl halides (67e), and 66 using Cu(II) complexes such as Fe 3 O 4 @SiO 2 NPs as the catalyst was carried out in water as the solvent to yield 1,4-substituted-1H-1,2,3-triazoles (71b) in 53-97% yield (Scheme 266). 479 The copper(I)-complexed silica-coated magnetite NP-[Cu(I) Fe 3 O 4 @SiO 2 ]-catalyzed synthesis of quinazolinones (134f) was achieved via the cyclocondensation of o-halobenzoic acids (82q) and substituted guanidine hydrochloride (174d) in 68-98% (Scheme 267).…”

Section: Bimetallic Np-catalyzed Synthesis Of Heterocyclesmentioning

confidence: 99%

A decennary update on applications of metal nanoparticles (MNPs) in the synthesis of nitrogen- and oxygen-containing heterocyclic scaffolds

et al. 2020

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“…Intramolecular reactions of 1-and 1,2-functionalized tetrahydro-, 1,2-and 3,4-dihydroisoquinolines are often used for annulation of the pyrrole core [31][32][33][34][35][36]. Recently, our group has demonstrated the preparation of functionally substituted on the pyrrole ring pyrrolo[2,1-a]isoquinolines based on domino reactions of 3,4-dihydro-1-aroylisoquinolines with electron-deficient alkynes, α,β-unsaturated aldehydes and cross-conjugated vinyl ethynyl ketones [37][38][39][40].…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of pyrrolo[2,1-a]isoquinolines by domino reaction of 1-aroyl-3,4-dihydroisoquinolines with conjugated ketones, nitroalkenes and nitriles

et al. 2020

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A convenient protocol for the synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines with various electron-withdrawing substituents at C-2 atom is described. This approach is based on the two-component domino reaction of 1-aroyl-3,4-dihydroisoquinolines with α,β-unsaturated ketones, nitroalkenes and acrylonitrile. Depending on the selected substrates, the reaction was performed in TFE under reflux or under microwave irradiation. Only for the two examples, a transition metal catalyst was used.

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Domino reactions of vinyl ethynyl ketones with 1-aryl-3,4-dihydroisoquinolines — Search for selectivity

Cited by 17 publications

References 30 publications

Reactivity of Cross-Conjugated Enynones in Cyclocondensations with Hydrazines: Synthesis of Pyrazoles and Pyrazolines

Reactivity of Cross-Conjugated Enynones in Cyclocondensations with Hydrazines: Synthesis of Pyrazoles and Pyrazolines

A decennary update on applications of metal nanoparticles (MNPs) in the synthesis of nitrogen- and oxygen-containing heterocyclic scaffolds

Facile synthesis of pyrrolo[2,1-a]isoquinolines by domino reaction of 1-aroyl-3,4-dihydroisoquinolines with conjugated ketones, nitroalkenes and nitriles

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