Synthesis of heterocyclic compounds by the reactions of exocyclic α,β‐unsaturated ketones

Lévai, Albert

doi:10.1002/jhet.5570410301

Cited by 17 publications

(7 citation statements)

References 123 publications

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“…The first synthesis of pyrazoline framework by the reaction of an , -enone with a hydrazine derivative was published by Fischer and Knovenagel in the late nineteenth century [8]. Then the reaction of , -unsaturated aldehydes and ketones with hydrazine derivatives became one of the most popular methods for the synthesis of pyrazolines [5][6][7][9][10][11][12]. Synthesis of tricyclic pyrazoles and pyrazolines by the reaction of the exocyclic , -unsaturated ketones with hydrazine derivatives has been achieved [13,14].…”

Section: Introductionmentioning

confidence: 99%

“…, -Unsaturated aldehydes and ketones are convenient and easily available starting materials or intermediates for the synthesis of a wide variety of heterocyclic compounds [5][6][7]. The first synthesis of pyrazoline framework by the reaction of an , -enone with a hydrazine derivative was published by Fischer and Knovenagel in the late nineteenth century [8].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Xie

Liu

et al. 2008

Journal of Heterocyclic Chem

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A series of 1-acetyl(or phenyl)-3-aryl-5-(1-phenyl-3-methyl-5-aryloxyl-pyrazol)-4,5-dihydropyrazole derivatives have been efficiently synthesized under refluxing in glacial acetic acid with two kinds of hydrazines and five kinds of chalcones of 1-phenyl-methyl-5-phenoxyl-pyrazol-4-aldehyde. The structures were confirmed on the basis of 1 H NMR, IR, MS and element analysis, and the crystal structure of the compound 4c was determined by single crystal X-ray diffraction. The compound 4c belongs to monoclinic system with space group P2(1)/n, a = 11.8779(3) nm, b = 12.0901(2) nm, c = 17.7004(4) nm, = 90°, = 100.05(10)°, = 90°, Formula weight: 549.46, Triclinic V =2502.89(9) nm 3 , D c =1.458 Mg/m 3 , Z = 4, F (000) = 1128.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Xie

Liu

et al. 2008

Journal of Heterocyclic Chem

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“…Then, the reaction of α,β-unsaturated aldehydes and ketones with hydrazine derivatives became one of the most popular methods for the synthesis of pyrazolines [34][35][36][37].…”

Section: Open Accessmentioning

confidence: 99%

Ultrasonics Promoted Synthesis of 5-(Pyrazol-4-yl)-4,5-Dihydropyrazoles Derivatives

et al. 2013

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A series of new 1,3-diaryl-5-(1-phenyl-3-methyl-5-chloropyrazol-4-yl)-4,5-dihydropyrazole derivatives have been synthesized under sonication conditions in ethanol or methanol/glacial acetic acid mixture (5/1 ratio) with two equivalents of hydrazines and seven kinds of chalcone-like heteroanalogues obtained from 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde. The structures were established on the basis of NMR, IR, MS and element analysis. This method provides several advantages over current reaction methodologies, including a simple work-up procedure, shorter reaction times (2-20 min) and good yields (65%-80%).

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“…Their cyclocondensation with dinucleophiles constitutes an important route to polycyclic fused ring systems, for example, tricyclic pyrazolines, tetracyclic benzothiazepines, tetracyclic benzodiazepines, thiazines, pyrimidines, quinazolines, and so forth [1][2][3][4]. Again, their 1,3-dipolar cycloaddition with different dipoles provides important nitrogen-containing spiroheterocycles [2].…”

Section: Introductionmentioning

confidence: 99%

An Expeditious and Safe Synthesis of Some Exocyclic α,β-Unsaturated Ketones by Microwave-Assisted Condensation of Cyclic Ketones with Aromatic Aldehydes over Anhydrous Potassium Carbonate

Mondal

Mandal

Mallik

2012

Organic Chemistry International

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A rapid, efficient, and solvent-free methodology for synthesis of exocyclic α,β-unsaturated ketones of the categories E-3-arylidene-4-chromanones, E-2-arylidene-1-tetralones, E-2-arylidene-1-indanones, E-3-cinnamylidene-4-chromanones, E-2-cinnamylidene-1-tetralones, E-2-cinnamylidene-1-indanones, α,α -(E,E)-bis(arylidene)-cycloalkanones, and α,α -(E,E)-bis (cinnamylidene)-cycloalkanones has been developed through cross-aldol condensation of the constituent cyclic ketones and aldehydes by microwave irradiation over anhydrous potassium carbonate. However, for condensation of 1-thio-4-chromanones with aromatic aldehydes by this method, the initially formed exocyclic α,β-unsaturated ketone has been found to undergo isomerization yielding 3-(arylmethyl)thiochromones.

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Synthesis of heterocyclic compounds by the reactions of exocyclic α,β‐unsaturated ketones

Cited by 17 publications

References 123 publications

Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Synthesis and crystal structure of 5‐pyrazol‐4,5‐dihydropyrazoles derivatives

Ultrasonics Promoted Synthesis of 5-(Pyrazol-4-yl)-4,5-Dihydropyrazoles Derivatives

An Expeditious and Safe Synthesis of Some Exocyclic α,β-Unsaturated Ketones by Microwave-Assisted Condensation of Cyclic Ketones with Aromatic Aldehydes over Anhydrous Potassium Carbonate

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