Synthesis of New Cyano-Quinoline Derivatives by the Baylis–Hillman Reaction (original) (raw)
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Synthesis and biological evaluation of some novel hetroaryl quinolinone derivatives
The aim of this study involves the synthesis of novel heterocyclic scaffolds containing quinoline moiety and studying their role as antimicrobial agents. 4-hydroxy-6-phenyl-2H-pyrano[3,2-c]quinoline-2,5(6H))-dione (1) was utilized as a precursor for the construction of new polyheterocyclic ring systems. It reacted with three aryl and (heteroaryl) aldehydes to furnish the corresponding arylidenes 2a-c. The nucleophilic cyclization of compound 2 with hydrazine hydrate to give pyrazolyl quinolinone 3. Moreover, the reaction of 1 with HCHO/morpholine led to the formation of the adduct 7. The synthesized N-(5-3-formyl-4-hydroxy-6-phenyl-2,5-dioxo-5,6-dihydro-2H-pyrano [3,2-c] quinoline (10) was utilized for the synthesis of 3-(([aryl]amino)methylene)-6-phenyl-2Hpyrano[3,2-c]quinoline-2,4,5 (3H,6H)-trione 11a-c via its treatment with three types of amines. Treatment of 1 with POCl3/Et3N afforded the corresponding 4-chloro derivative 20. Which upon treatment with thiourea lead to the formation of the corresponding 4-mercapto derivative 21. The latter 21 was alkylated using ethylbromo acetate giving 22. All freshly synthesized scaffolds were elucidated by considering the data of both elemental and spectral analyses. The synthesized scaffolds were screened for antimicrobial activities also showed promising results. The p-chlorobenzylidene pyrazolylquinolone derivative 3 has excellent antimicrobial properties against Proteus vulgaris compared to its mild activity against Staph aureus. While 4-Chloro-6-phenyl-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione (20) exhibited good activates against Staph aureus surpassing the activity of reference antibiotic. Also, compounds 21 showed excellent antifungal activity against Candida albicans higher than fluconazole.
European Journal of Organic Chemistry, 2009
The synthesis of a variety of polycyclic quinolines is described. The target molecules were obtained in two steps by an initial reductive cyclization followed by another intramolecular cyclization in the allylamines afforded from either the acetates or allyl bromides of Baylis–Hillman adducts of 2-nitrobenzaldehydes and acrylonitrile. The two steps proceeded in one-pot for those substrates in which a formyl or hydroxy group reacted with the amino group of the 2-aminoquinoline in the second intramolecular cyclization. In contrast, a basic medium was necessary for the second intramolecular cyclization reaction in substrates in which an alkoxycarbonyl group and the amino group participated. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Synthesis, Characterization and Conformational Analysis of Two Novel 4(1H)‑Quinolinones
Journal of the Brazilian Chemical Society
Quinolinones are a class of organic compounds known as alkaloids found in several plants and also can be synthesized. Their large use in therapies regards their wide biological potential like antitumor, psychiatric and neurological agents. Two substances were structurally characterized: (E)-3-(2-nitrobenzylidene)-2-(4-methoxyphenyl)-1-(phenylsulfonyl)-2,3-dihydroquinolin-4(1H)-one (NMQ), and (E)-3-(2-chlorobenzylidene)-2-(2-methoxyphenyl)-1-(phenylsulfonyl)-2,3-dihydroquinolin-4(1H)-one (CMQ). These compounds were synthesized, crystallized, characterized by single crystal X-ray diffraction and theoretical calculations. The NMQ and CMQ crystals are formed by a pair of enantiomers and crystallized in the centrosymmetric group P21/c with similar volume and density. Differences noted on crystal packing and supramolecular arrangement are associated to substituent group chlorine in CMQ and nitro in NMQ. The calculated infrared (IR) spectra show a good agreement with experimental values. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies show CMQ more kinetically stable with a higher resistance to transfer charge than NMQ.
Synthesis and Biological Activity Investigation of Some Quinoline-2-One Derivatives
2015
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 N-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 p-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 salicyald...
Developments in Quinoline Synthesis: A Review
Quinoline ring structure is obtained by o-condensation of benzene ring with pyridine. It is also called l-azanaphthalene or benzo[b]pyridine. Since first synthesis quinoline, number of methods has been discovered to enhance reaction yield, decrease reaction time as well as reduce hazardous reagents and reaction conditions. Compound with quinoline core are widely used for industrial purposes and also exhibit a broad range of biological activities. An overview of synthetic methodologies used for the construction of quinoline ring is also described.