Selective Synthesis Dispiro[indoline‐3,2′‐pyrrolidine‐3′,3″‐quinoline] Derivatives and Spiro[imidazole‐4,3′‐quinoline] Derivatives via 1,3‐Dipolar Cycloaddition Reaction

Hamama, Wafaa S.; Hassanien, Alaa E.; El-Fedawy, Manal G.; Zoorob, Hanafi H.

doi:10.1002/jhet.2646

Cited by 7 publications

(1 citation statement)

References 21 publications

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“…[19][20][21] In particular, cycloaddition of various azolones with exocyclic double bond is very promising strategy for the creation of spirocyclic core (Scheme 2). [20,[22][23][24][25][26][27] Among others, such a simple and readily available reagent as N-benzyl-1-(trimethylsilyl)-N-(methoxymethyl)methanamine (compound I, Scheme 2), which easily generates N-benzylazomethine methylide, is of special interest. [15,28,29] It is used for the synthesis of tetrahydropyrroles (pyrrolidines) that are unsubstituted at the second and fifth positions.…”

Section: Introductionmentioning

confidence: 99%

[3+2] Cycloaddition of N‐benzylazomethine Methylide with Various Arylidene‐Azolones

Tiushina,

Sokolov,

Smirnov

et al. 2024

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Section: Introductionmentioning

confidence: 99%

[3+2] Cycloaddition of N‐benzylazomethine Methylide with Various Arylidene‐Azolones

Tiushina,

Sokolov,

Smirnov

et al. 2024

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Pyrimido[5,4‐c]quinolines: Synthesis from 3,4‐Di‐functionallized Quinoline, Reactivity and Biological Activities

Gouda,

Abu‐Hashem,

Ameen

et al. 2024

Chemistry & Biodiversity

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Quinoline and pyrimidine moieties are ubiquitous components in both natural and synthetic compounds, showcasing diverse applications. The fusion of these well‐known structures into hybrid molecules has garnered attention due to their intriguing biological properties. Particularly in the field of medicinal chemistry, numerous studies in the last decade have focused on pyrimido[5,4‐c]quinoline ring systems (PyQs5,4‐c). This review elucidates the synthesis of PyQs5,4‐c and their derivatives using 3,4‐difunctionalized quinoline as a key starting material. The preparation of PyQs5,4‐c involves a series of chemical transformations, including the Friedländer, Ullmann andBiginelli reaction, Vilsmeier‐Haack formylation, Suzuki coupling, and a one‐pot three‐component reaction. These synthetic routes not only offer access to diverse PyQs5,4‐c derivatives but also contribute to the expanding arsenal of methods in the synthesis of biologically relevant compounds.

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Efficient Synthesis, Antimicrobial, Antioxidant Assessments and Geometric Optimization Calculations of Azoles‐ Incorporating Quinoline Moiety

Hamama

Ibrahim

Gooda

et al. 2018

Journal of Heterocyclic Chem

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A novel series of Schiff bases, hydrazide, and hydrazine derivatives containing quinoline moiety were synthesized via condensation of 3-substituted quinolines 1a and 1b with different aromatic amines or hydrazines. Furthermore, various heterocyclic ring systems: 1,3,4-thiadiazole, thiazolidin-4-one, 2-thioxoimidazolidin-4-one, and thiazole derivatives 10-13 were synthesized by refluxing hydrazinecarbothioamide derivative 9 with different acetic acid derivatives. Theoretical calculation of the title compounds were carried out using density functional theory method. The geometrical optimization of the prepared target compounds was theoretically analyzed. The synthesized compounds were examined for their antimicrobial and antioxidant activities. The obtained results revealed clearly that compounds 8 and 13 displayed promising activity as an antimicrobial activity and compounds 3, 5, 6, 7, and 9 exhibited better radical scavenging ability. Scheme 3. Transformation reaction of thiosemicarbazone derivative 9 to quinolone-attached 5-membered heterocyclic moieties 10-13. Scheme 2. Reaction of 2-substituted quinoline-3-carbaldehyde 1a and 1b with hydrazine derivatives.

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Selective Synthesis Dispiro[indoline‐3,2′‐pyrrolidine‐3′,3″‐quinoline] Derivatives and Spiro[imidazole‐4,3′‐quinoline] Derivatives via 1,3‐Dipolar Cycloaddition Reaction

Cited by 7 publications

References 21 publications

[3+2] Cycloaddition of N‐benzylazomethine Methylide with Various Arylidene‐Azolones

[3+2] Cycloaddition of N‐benzylazomethine Methylide with Various Arylidene‐Azolones

Pyrimido[5,4‐c]quinolines: Synthesis from 3,4‐Di‐functionallized Quinoline, Reactivity and Biological Activities

Efficient Synthesis, Antimicrobial, Antioxidant Assessments and Geometric Optimization Calculations of Azoles‐ Incorporating Quinoline Moiety

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