Recent Advances in the Friedländer Reaction

Marco‐Contelles, José; Pérez‐Mayoral, Elena; Samadi, Abdelouahid; Carreiras, María do Carmo; Soriano, Elena

doi:10.1021/cr800482c

Cited by 614 publications

(384 citation statements)

References 451 publications

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“…The formation of 2,2,2-trifluoro-1-(2-methyl-1,8-naphthyridin-3-yl) ethanone (3a) was confirmed by the presence of aromatic cyclic peaks at 3099, 3036, C=N is stretching peaks The mechanism of microwave synthesis of 1,8-naphthyridines [28] is given in Fig. 2.…”

Section: Resultsmentioning

confidence: 90%

Green Synthesis, Cyclization and Biological Study of Novel Series of 1,8-Naphthyridines Using Friedlander Condensation

Nandhikumar¹,

Subramani²

2018

Asian J. Chem.

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Section: Resultsmentioning

confidence: 90%

Green Synthesis, Cyclization and Biological Study of Novel Series of 1,8-Naphthyridines Using Friedlander Condensation

Nandhikumar¹,

Subramani²

2018

Asian J. Chem.

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“…Similarly, a mixture of compounds 20 and 21 (Chart 1) was obtained by Friedlander reaction 45,46 of compound 30 with ketone 33 (Scheme 5) using pyrrolidine as catalyst. 48 The structures of the resulting quinolinodonepezils 20 and 21 were determined by H NMR spectrum of compound 20, as well as two singlets at δ 7.53 and 2.76, integrating for one and three protons, and corresponding to H5 and C(7)CH 3 , respectively, in the 1 H NMR spectrum of compound 21, clearly support the structure of the Friedlander products.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis, Pharmacological Assessment, and Molecular Modeling of Acetylcholinesterase/Butyrylcholinesterase Inhibitors: Effect against Amyloid-β-Induced Neurotoxicity

Silva

Chioua

Samadi

et al. 2013

ACS Chem. Neurosci.

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ABSTRACT:The synthesis, molecular modeling, and pharmacological analysis of phenoxyalkylamino-4-phenylnicotinates (2−7), phenoxyalkoxybenzylidenemalononitriles (12, 13), pyridonepezils (14−18), and quinolinodonepezils (19−21) are described. Pyridonepezils 15−18 were found to be selective and moderately potent regarding the inhibition of hAChE, whereas quinolinodonepezils 19−21 were found to be poor inhibitors of hAChE. The most potent and selective hAChE inhibitor was ethyl 6-(4-(1-benzylpiperidin-4-yl)butylamino)-5-cyano-2-methyl-4-phenylnicotinate (18) [IC 50 (hAChE) = 0.25 ± 0.02 μM]. Pyridonepezils 15−18 and quinolinodonepezils 20−21 are more potent selective inhibitors of EeAChE than hAChE. The most potent and selective EeAChE inhibitor was ethyl 6-(2-(1-benzylpiperidin-4-yl)ethylamino)-5-cyano-2-methyl-4-phenylnicotinate (16) [IC 50 (EeAChE) = 0.0167 ± 0.0002 μM], which exhibits the same inhibitory potency as donepezil against hAChE. Compounds 2, 7, 13, 17, 18, 35, and 36 significantly prevented the decrease in cell viability caused by Aβ 1−42 . All compounds were effective in preventing the enhancement of AChE activity induced by Aβ 1−42 . Compounds 2−7 caused a significant reduction whereas pyridonepezils 17 and 18, and compound 16 also showed some activity . The pyrazolo [3,4-b]quinolines 36 and 38 also prevented the upregulation of AChE induced by Aβ 1−42 . Compounds 2, 7, 12, 13, 17, 18, and 36 may act as antagonists of voltage sensitive calcium channels, since they significantly prevented the Ca 2+ influx evoked by KCl depolarization. Docking studies show that compounds 16 and 18 adopted different orientations and conformations inside the active-site gorges of hAChE and hBuChE. The structural and energetic features of the 16-AChE and 18-AChE complexes compared to the 16-BuChE and 18-BuChE complexes account for a higher affinity of the ligand toward AChE. The present data indicate that compounds 2, 7, 17, 18, and 36 may represent attractive multipotent molecules for the potential treatment of Alzheimer's disease.

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“…Alternatively, it has been proposed that the initial ratelimiting step is an intermolecular aldol reaction furnishing the quinoline. 7 However, regarding the substrate, it has been studying here, another mechanism seems to be operating, where the reaction is likely to occur by the initial formation of an enamino intermediate (IIa-IIb). This can be evidenced by the fact that during the optimization steps of reaction, it was occasionally isolated the enamino ketone intermediate.…”

Section: Reaction Time Was Also Analyzed the Reaction Time Using [Bmmentioning

confidence: 89%

“…[2][3][4][5] The most described synthetic route to quinolines is known as Friedländer annulations. 6,7 In this reaction, substituted anilines or 2-carbonyl-substituted anilines (C-C-C-N unit) react with carbonyl compounds containing a reactive α-methylene group (C-C unity). Generally, the reactive α-methylene group is part of unsymmetrical ketones, 8 1,3-dicarbonyl compounds 9 or β-ketoesters.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel quinolines using TsOH/ionic liquid under microwave

Prola

Buriol

Frizzo

et al. 2012

J. Braz. Chem. Soc.

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Neste trabalho, 3-haloacetil-4-metilquinolinas foram sintetizadas a partir da reação de 4-alcóxi-3-alquen-2-onas [R In this work, 3-haloacetyl-4-methylquinolines were synthesized from the reaction of 4-alkoxy-3-alken-2-ones [R 1 C(O)CH=C(R 2 )OCH 3 , where R 1 = CF 3 , CCl 3 , CHCl 2 , CF 2 Cl, CF 2 CF 3 and R 2 = Me, Et, Pr, Bu, i-Bu and i-Pe] and 2-aminoacetophenone. The reaction was performed in ionic liquid and 4-toluene sulfonic acid under microwave irradiation. Results showed that the catalytic method was effective. Products were formed in a short time (10-20 min) and presented good yields (70-91%).

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Recent Advances in the Friedländer Reaction

Cited by 614 publications

References 451 publications

Green Synthesis, Cyclization and Biological Study of Novel Series of 1,8-Naphthyridines Using Friedlander Condensation

Green Synthesis, Cyclization and Biological Study of Novel Series of 1,8-Naphthyridines Using Friedlander Condensation

Synthesis, Pharmacological Assessment, and Molecular Modeling of Acetylcholinesterase/Butyrylcholinesterase Inhibitors: Effect against Amyloid-β-Induced Neurotoxicity

Synthesis of novel quinolines using TsOH/ionic liquid under microwave

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