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Synthesis of derivatives of 2 phenyl quinoline 4 carboxylic acid Welcome to the IDEALS Repository

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Preparation of 4-(bromomethyl)quinoline

Dimethyl acetylenedicarboxylate (1.136g, 8mmol) was added to a solution of aniline (1.48g, 15.91 mmol) in ethanol (5ml) and the mixture stirred overnight at room temperature. Benzaldehyde (0.848g, 8 mmol) and p-toluene sulfonic acid (0.344g, 2 mmol) were added to the solution with further stirring for 48h. Solid product separated out, was collected, washed with cold ethanol, and recrystallized from ethanol to give pale green crystals for dimethyl(2R,3S,4R)-2-phenyl-4-(phenylamino)-1,3,4 - trihydroquinoline - 2, 3-dicarboxylate (12), m.p., 177-179 ̊C , (yield : 1.66g, 48%). max (EtOH) : 207 , 253 ,and 292 nm. max (KBr) : 3260 , 3210 (N-H) ; 3050 (-C6H5); 2930 (CH-aliph.) ; 1700 , 1680 ( 2C=O) ; 1230 ( C-O) , and 1060 cm -1 (C-N).

4-Phenyl quinoline derivatives as ..
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Because the chloroquine prevent the development of malaria parasites in the blood so it is used by doctors to both prevent and treat malaria. 11 Simple quinoles (3-6) are isolated from the bark of Galipea longiflora trees of the Rutaceae family 12-14 used effectively against the parasites Leishmania sp., which are the agents of Leishmaniasis, a protozoan disease of the tropical areas in South Africa, particularly in the amazonian forest.15 Previous publications have clearly demonstrated many reactions in various synthetic applications which give rise to quinoline nucleus. 16-19 The most versatile method available for the synthesis of quinoline derivatives is the reaction of 2-aminoacetophenon and ethyl acetoacetate in the presence of chloramine-T and acetonitrile as a solvent to afford (7). 20, 21

4-Phenyl quinoline derivatives as potential serotonin receptor ..

synthesis of quinoline derivatives by reaction of dimethyl(2r,3s,4r)-2-phenyl-4-(phenylamino)-1,3,4-trihydroquinoline-2,3-dicarboxylate with some amines
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New quinoline-2-one derivatives were synthesized by reaction of 4,7-dimethyl coumarin (I) with nitric acid in the presence of concentrated sulfuric acid to afford 4,7-dimethyl-6-nitrocoumarin (II) and 4,7-dimethyl-8-nitrocoumarin (III). The compound (II) was treated with hydrazine hydrate (80% in pyridine) to give -amino-4,7-dimethy- 6-nitroquinoline-2-one (IV). The latter was used to synthesize 1-(4,7-dimethyl-6-nitro-2-oxo-2H-quinolin-1-yl) -3-phenyl-urea (V) and 1-(4,7-dimethyl-6-nitro-2-oxo-2H-quinolin-1-yl)-3-phenyl-thiourea (VI) by the reaction of (IV) with phenyl isocyanate and phenyl isothiocyanate, respectively. Cyclization of compounds (V) and (VI) with phenyl phenacyl bromide gave the corresponding oxazole (VII) and thiazole (VIII), respectively. The diacetylamino derivative (IX) and mono benzoylamino derivative (X) were prepared by reaction of compound (IV) with acetic anhydride and benzoyl chloride, respectively. Subsequently, compound (IV) was reacted with salicyaldehyde to synthesize the corresponding Schiff base (XI). The synthesized compounds were characterized by FTIR, H-NMR, 13C-NMR and by measurements some of their physical properties. Finally, the prepared compounds were evaluated for biological activities against two types of bacteria.

T1 - Design, synthesis and biological evaluation of4-(Imidazolylmethyl)- 2-(4-methylsulfonyl phenyl)-quinoline derivatives as selective COX-2 inhibitors and in-vitro anti-breast cancer agents

The 4-phenyl quinoline analogs were prepared ..

Abstract Synthesis, Charcterization and Antibacterial Studies of 4-Methyl-2-(4-Substituted Phenyl) Quinoline Derivatives Author(s): S.S
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In view of significant interest in the synthesis of these heterocyclic, we herein report in a detailed account of the synthetic methods available for the synthesis of (12). In a typical experiment, aniline, dimethyl acetylenedicarboxylate (DMAD) and benzaldehyde were reacted in presence of p-toluene sulfonic acid in absolute ethanol with stirring to afford the corresponding product, dimethyl (2R,3S,4R)-2-phenyl-4-(phenylamino)- 1, 3, 4-tryhydroquinoline-2,3-dicarboxylate (12) in moderate yield. The reaction was completed within 72 hours, as it can be seen below:

As a part of our continued interest in the development of new synthetic methods for further highly substituted fused rings to quinoline nucleus, we have developed a new synthetic route mainly to the synthesize of pyrroloquinolines derivatives through unprecedented approach from dimethyl (2R,3S,4R)-2-phenyl - 4 - (phenylamino)-1,3,4-trihydroquinoline-2,3-dicarboxylate (12) and amines.

Synthesis and molecular validation of 6-substituted-2-(3-phenoxyphenyl)-4-phenylquinoline derivatives (4a-h) as antibacterial/DNA gyrase inhibitors reported.
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    Quinoline - Wikipedia

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Synthesis of m-anisidine Synthesis of quinoline


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There is a facile and efficient iron-catalyzed intramolecular allylic amination of 2-aminophenyl-1-en-3-ols which proceeds smoothly to afford 1,2-dihydroquinoline and quinoline derivatives such as (8) and under further mild reaction conditions gives good yields of (9). 22 Also, 1,4-dihydroquinolines such as (11) has been reported through sequential N-acylamide (10) methylenation-enamide ring-closing metathesis. 23

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