Synthesis of pyrazoline derivatives from the 1,3-dipolar cycloadditions using α,β-unsaturated cyclohexanone derivatives

Ziani, Nouara; Lamara, Kaddour; Sid, Assia; Willem, Quentin; Dassonneville, Benjamin; Demonceau, Albert

doi:10.5155/eurjchem.4.2.176-179.757

Cited by 10 publications

(4 citation statements)

References 37 publications

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“…PDBA (0.2 g, 5.49 mmol) and hydrazine hydrate (0.18 mL, 0.3 mmol) in 5 mL glacial acetic acid [38] (Scheme 1) were taken in 25 mL round-bottom flask and heated to 115 °C for 24 h. The content was cooled and poured into crushed ice, the resulting precipitate was filtered, and then reprecipitated with MeOH. The polymer was characterized by 1 H NMR (see Figure S6, Supporting Information).…”

Section: Synthesis Of Ppy1 and Ppy2mentioning

confidence: 99%

Synthesis and Characterization of Solution Processable Poly(pyrazolines)

Jayalakshmi

Keerthika

Santhanagopal

2020

Macro Chemistry & Physics

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Solution‐processable poly(dibenzalacetone) and poly(dibenzalcyclohexanone) are prepared by the condensation of 1,4‐dialkoxy‐bisbenzaldehyde and acetone/cyclohexanone using classic Claisen–Schmidt condensation. The prepared polymers are readily soluble in common organic solvents due to the presence of alkoxy chains present on the aromatic ring. The availability of α,β‐unsaturated ketone on the backbone is readily functionalized with hydrazine hydrate to obtain poly(pyrazoline acetate), a nonconjugated polymer on the backbone, which shows enhanced emission characteristics on comparison with the pristine polymer and small molecule analogues. The highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO–LUMO) of levels of poly(pyrazolines) has a band gap of 1.54 eV as calculated from cyclic voltammetry and UV–vis studies. Uniform thin film is obtained by spin casting as 1% solution on chlorobenzene and annealing under vacuum. Atomic force microscopy analysis shows fine morphology of the thin film. I–V characterization of the film shows low turn‐on voltage of 5.3 V. HOMO–LUMO is calculated by density functional theory and the result suggests that these molecules have great potential toward polymer organic light‐emitting diode applications.

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Section: Synthesis Of Ppy1 and Ppy2mentioning

confidence: 99%

Synthesis and Characterization of Solution Processable Poly(pyrazolines)

Jayalakshmi

Keerthika

Santhanagopal

2020

Macro Chemistry & Physics

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“…This moiety is a characteristic functionality of biologically and synthetically important compounds known as chalcones. This synthon is considered as a versatile building block that can be used to construct heterocyclic rings having one or more heteroatoms and of di erent ring sizes such as 2-pyrazoline [1], pyrimidine [2,3], pyran, and isooxazoline [4]. Generally chalcones and their analogs are prepared by Claisen-Schmidt reactions under basic conditions using bases such as sodium hydroxide or potassium hydroxide [5], lithium hydroxide [6] and piperidine [7].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C₁₉H₁₈O₄

El-Sayed

Almaneai

Ghabbour

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Pyrazoline [1] (dihydropyrazole) derivatives find vital applications as pharmacores, [2,3] synthons, [2,3] photosensitizers [4–6] and wavelength shifters [7] in pharmaceutical, [8] polymer [9] and dye industries. [5.6] These five membered electron rich nitrogen heterocycles consist of two adjacent nitrogens and one endocyclic double bond within the ring.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the Substituent Effects in the Stereochemistry of [3+2] Cycloaddition Reactions of Aryl‐ and Alkyldiazomethylphosphonates with Norbornadiene within a MEDT Perspective

Domingo

Acharjee

2021

ChemistrySelect

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The [3 + 2] cycloaddition (32CA) reactions of norbornadiene with aryl and alkyl substituted diazomethylphosphonates (SDAPs) have been studied within the molecular electron density theory (MEDT). Electron localization function (ELF) shows the presence of a pseudoradical C3 center at the alkyl SDAPs, classifying them as pseudo(mono)radical species, while the aryl SDAP is classified as a zwitterionic one, owing to the delocalization of the C3 electron density on the C3-P bond. These 32CA reactions present high activation enthalpies in dichloromethane, between 17.3 and 21.6 kcal mol À 1 , being strongly exothermic by more than 33.8 kcal mol À 1 . While these 32CA reactions present a total syn facial selectivity, the endo/ exo stereoselectivity depends on the steric hindrance caused by the bulk substituents present in these SDAPs along the approach to norbornadiene. Interestingly the phenyl group provokes a lesser hindrance than that of the small methyl group, justifying the 95 % of exo stereoselectivity experimentally observed. ELF and the AIM (Atoms-in-Molecules) analyses account for the bonding changes along these 32CA reactions. The energy cost for the rupture of the norbornadiene CÀ C and that of the SDAPs NÀ N double bonds are the major contributors to the activation energies of these non-polar 32CA reactions.

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Synthesis of pyrazoline derivatives from the 1,3-dipolar cycloadditions using α,β-unsaturated cyclohexanone derivatives

Cited by 10 publications

References 37 publications

Synthesis and Characterization of Solution Processable Poly(pyrazolines)

Synthesis and Characterization of Solution Processable Poly(pyrazolines)

Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C₁₉H₁₈O₄

Unveiling the Substituent Effects in the Stereochemistry of [3+2] Cycloaddition Reactions of Aryl‐ and Alkyldiazomethylphosphonates with Norbornadiene within a MEDT Perspective

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Synthesis of pyrazoline derivatives from the 1,3-dipolar cycloadditions using α,β-unsaturated cyclohexanone derivatives

Cited by 10 publications

References 37 publications

Synthesis and Characterization of Solution Processable Poly(pyrazolines)

Synthesis and Characterization of Solution Processable Poly(pyrazolines)

Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H18O4

Unveiling the Substituent Effects in the Stereochemistry of [3+2] Cycloaddition Reactions of Aryl‐ and Alkyldiazomethylphosphonates with Norbornadiene within a MEDT Perspective

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Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C₁₉H₁₈O₄