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An isoxazole strategy for the synthesis of 4-oxo-1,4-dihydropyridine-3-carboxylates.

ABSTRACT: A method has been developed for the preparation of 2-alkyl-6-aryl-, 2-aryl-6-aryl and 2,6-diaryl-5-aryl/hetaryl-substituted methyl 4-oxo-1,4-dihydropyridine-3-carboxylates by Mo(CO)₆-mediated ring expansion of methyl 2-(isoxazol-5-yl)-3-oxopropanoates. The high reactivity of 4-oxo-1,4-dihydropyridine-3-carboxylates synthesized provide easy access to 2,4,6-triaryl-substituted and 1,2,5,6-tetrasubstituted nicotinates.

SUBMITTER: Zanakhov TO

PROVIDER: S-EPMC9235835 | biostudies-literature |

REPOSITORIES: biostudies-literature

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First Organocatalytic Asymmetric Synthesis of 1-Benzamido-1,4-Dihydropyridine Derivatives.

Project description:Preliminary results concerning the first asymmetric synthesis of highly functionalized 1-benzamido-1,4-dihydropyridine derivatives via the reaction of hydrazones with alkylidenemalononitriles in the presence of ?-isocupreidine catalyst are reported. The moderate, but promising, enantioselectivity observed (40?54% ee), opens the door to a new area of research for the asymmetric construction of new chiral 1,4-dihydropyridine derivatives, whose enantioselective catalytic preparation are still very limited. Moreover, the use of hydrazones for the enantioselective construction of chiral 1,4-dihydropyridines has been overlooked in the literature so far. Therefore, our research represents a pivotal example in this field which remains still unexplored.

| S-EPMC6222298 | biostudies-literature

Calcined Layered Double Hydroxides: Catalysts for Xanthene, 1,4-Dihydropyridine, and Polyhydroquinoline Derivative Synthesis.

Project description:This work is generally focused on the synthesis of NiFeTi-layered double hydroxides (LDHs) using a hydrothermal route, which were calcined at various temperatures (varying from 200 to 600 °C). The synthesized materials were physicochemically characterized. X-ray diffraction results revealed the loss of the layered structure on calcination resulting in the formation of layered double oxides (LDOs) or mixed metal oxides, which was also supported by Fourier transform infrared studies. Scanning electron microscopy results also show loss of the layered structure and the creation of LDOs on increasing the temperature. These LDOs were tested as the catalysts for the synthesis of biologically significant xanthene, 1,4-dihydropyridine, and polyhydroquinoline derivatives. Among all, NiFeTi LDH calcined at 600 °C proved to be the best catalyst for the synthesis of these derivative compounds under optimized conditions. The advantages obtained were excellent yields in a lesser reaction time. Stability and reusability were also assessed; the catalyst was stable even after five cycles. Furthermore, the memory effect of the obtained NiFeTi CLDH calcined at 600 °C confirms that the material so formed is a calcined state of LDH itself. High catalytic efficiency, easy fabrication, and recycling ability of NiFeTi CLDH calcined at 600 °C make it a potential catalyst for the synthesis of xanthene, 1,4-dihydropyridine, and polyhydroquinoline derivatives.

| S-EPMC7331214 | biostudies-literature

4,4'-Bipyridinium bis-(μ-4-oxo-1,4-dihydropyridine-2,6-dicarboxyl-ato)bis-[aqua-hydroxido-anti-monate(III)] dihydrate.

Project description:The title compound, (C(10)H(10)N(2))[Sb(2)(C(7)H(2)NO(5))(2)(OH)(2)(H(2)O)(2)]·2H(2)O, consists of a binuclear anion, a diprotonated 4,4'-bipyridinium cation and two uncoordinated water mol-ecules. Each Sb(III) atom is six-coordinated by one chelating 4-oxidopyridine-2,6-dicarboxyl-ate ligand, one water mol-ecule, one OH group and one bridging O atom from a neighboring carboxyl-ate group in a distorted penta-gonal-pyramidal geometry, with the OH group at the apical position. The two pyridine rings in the bipyridinium cation are twisted with respect to each other, making a dihedral angle of 22.7 (1)°. The cations are connected to the anions by N-H⋯O hydrogen bonds, forming a chain. The coordinated water mol-ecules form hydrogen bonds with the oxido O atoms of the anion, building a two-dimensional sheet, which is further connected into a three-dimensional structure by O-H⋯O and C-H⋯O hydrogen bonds and C=O⋯π inter-actions [O⋯centroid distances = 3.1785 (17), 3.4737 (19) and 3.5685 (19) Å].

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Organocatalyzed enantioselective synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylates.

Project description:The organocatalyzed enantioselective synthesis of biologically active 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate derivatives was achieved using bifunctional cinchona alkaloids as the catalysts. Using quinine thiourea as the catalyst, the tandem Michael addition-cyclization reaction between 1,3-cyclohexanediones and alkylidenecyanoacetate derivatives gives the desired products in high yields (up to 92%) and good ee values (up to 82%).

| S-EPMC3212733 | biostudies-literature

Intramolecular hydrogen bonds in 1,4-dihydropyridine derivatives.

Project description:1,4-Dihydropyridine (1,4-DHP) derivatives have been synthesized and characterized by 1H, 13C, 15N nuclear magnetic resonance (NMR) spectroscopy, secondary proton/deuterium 13C isotope shifts, variable temperature 1H NMR experiments and quantum-chemical calculation. The intramolecular hydrogen bonds NH?O=C and CH?O=C in these compounds were established by NMR and quantum-chemical studies The downfield shift of the NH proton, accompanied by the upfield shift of the 15N nuclear magnetic resonance signals, the shift to the higher wavenumbers of the NH stretching vibration in the infrared spectra and the increase of the 1J(15N,1H) values may indicate the shortening of the N-H bond length upon intramolecular NH?O=C hydrogen bond formation.

| S-EPMC6030305 | biostudies-literature

Fluorescent probes of the isoxazole-dihydropyridine scaffold: MDR-1 binding and homology model.

Project description:Isoxazole-1,4-dihydropyridines (IDHPs) were tethered to fluorescent moieties using double activation via a lanthanide assisted Weinreb amidation. IDHP-fluorophore conjugate 3c exhibits the highest binding to date for IDHPs at the multidrug-resistance transporter (MDR-1), and IDHP-fluorophore conjugates 3c and 7 distribute selectively in SH-SY5Y cells. A homology model for IDHP binding at MDR-1 is presented which represents our current working hypothesis.

| S-EPMC3987963 | biostudies-literature

Green approach for synthesis of bioactive Hantzsch 1,4-dihydropyridine derivatives based on thiophene moiety via multicomponent reaction.

Project description:A novel green and efficient one-pot multicomponent reaction of dihydropyridine derivatives was reported as having good to excellent yield. In the presence of the catalyst ceric ammonium nitrate (CAN), different 1,3-diones and same starting materials as 5-bromothiophene-2-carboxaldehyde and ammonium acetate were used at room temperature under solvent-free condition for the Hantzsch pyridine synthesis within a short period of time. All compounds were evaluated for their in vitro antibacterial and antifungal activity and, interestingly, we found that 5(b-f) show excellent activity compared with Ampicillin, whereas only the 5e compound shows excellent antifungal activity against Candida albicans compared with griseofulvin. The cytotoxicity of all compounds has been assessed against breast tumour cell lines (BT-549), but no activity was found. The X-ray structure of one such compound, 5a, viewed as a colourless block crystal, corresponded accurately to a primitive monoclinic cell.

| S-EPMC5493906 | biostudies-literature

Intramolecular C-H···O hydrogen bonding in 1,4-dihydropyridine derivatives.

Project description:The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH···O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.

| S-EPMC6264772 | biostudies-literature

1,1'-[4-(2-Methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-diyl]diethanone.

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| S-EPMC2971406 | biostudies-literature

Synthesis and Utility of Dihydropyridine Boronic Esters.

Project description:When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products.

| S-EPMC4769604 | biostudies-literature

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