- Structure of 2,3-dicarboxy-1-methylpyridinium chloride studied by X-ray diffraction, DFT calculation, NMR, FTIR and Raman spectra
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The structure of 2,3-dicarboxy-1-methylpyridinium chloride (1) has been studied by X-ray diffraction, DFT calculations, NMR, FTIR and Raman spectra. The crystals are monoclinic, space group P21/c. Chloride anion links two 2,3-dicarboxy-1-methylpyridinium cations into infinite zigzag chains down the [0 0 1] direction by the OH?Cl-?HO hydrogen bonds of 2.970(2) and 3.011(2) ?. Hydrogen bond lengths in single molecules (2-4) optimized by the B3LYP/6-311++G(d,p) approach depend on the environment and intramolecular O·H·O hydrogen bond. Linear correlations between the experimental 13C and 1H chemical shifts (δexp) of the investigated compound in DMSO-d6 and the GIAO/B3LYP/6-311++G(d.p) magnetic isotropic shielding constants (σcalc) calculated using the screening solvation model (COSMO), δexp = a + b σcalc, are reported. The FTIR spectrum of the solid compound is consistent with the X-ray structure. The deformation in-plane and out-of-plane OH vibrations, both in FTIR and second-derivative (d2) spectra, appear as two bands consistent with the OH?Cl-?HO arrangement.
- Barczyński,Szafran,Ratajczak-Sitarz,Nowaczyk,Dega-Szafran,Katrusiak
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- Zinc and Cadmium Complexes of Pyridinemethanol Carboxylates: Metal Carboxylate Zwitterions and Metal–Organic Frameworks
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The heterofunctional lactone furo[3,4-b]pyridin-5(7H)-one (L1) undergoes a coordination-induced ring-opening reaction with Zn(NO3)2 ? 6H2O to yield the zwitterionic [Zn(L1′)2(H2O)2] (1, L1′=2-(hydroxymethyl)nicotinate) with an uncoordinated carboxylate. The same reaction with Cd(NO3)2 ? 4H2O provides a two-dimensional (2D) network of [Cd(L1′)2]n (3) with the carboxylates coordinated to cadmium(II) propagating the assembly. The corresponding reactions of Zn(NO3)2 ? 6H2O and Cd(NO3)2 ? 4H2O with 2-(hydroxymethyl)isonicotinic acid (HL2) generated zwitterionic [Zn(L2)2(H2O)2] (2) and a 2D network [Cd(L2)2]n?nDMF (4, DMF=N,N′-dimethylformamide), respectively. Complexes 1–4 are weakly emissive, giving ligand-centered emissions at 409 nm (1), 412/436 nm (2), 404 nm (3), and 412/436 nm (4) in CHCl3 solutions upon excitation at 330 nm. This work points to the potential of using ‘hidden’ functionalities widely found in small organic molecules and natural products for the construction of coordination complexes with new functionality and potential applications.
- Lin, Shi-Xin,Liu, Quan,Liu, Yan,Niu, Ru-Jie,Young, David J.,Zhang, Wen-Hua
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- Transition-Metal-Free Synthesis of Pyridine Derivatives by Thermal Cyclization of N -Propargyl Enamines
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A transition-metal-free synthesis of pyridine derivatives by 6- endo - dig cyclization of N -propargyl enamines was developed. This method is environmentally friendly and is a high atom economy reaction that is easily accessed to provide pyridine derivatives in moderate to good yield by heating N -propargyl enamines in solvent without additives. The total synthesis of onychine was achieved in 51% yield in only two steps by using this method.
- Chikayuki, Yuya,Higashiyama, Kimio,Kirita, Akiko,Matsuo, Natsuko,Miyashige, Takakane,Sasaki, Shigeru,Teramoto, Hiroyoshi,Yamauchi, Takayasu,Yonekawa, Shiori
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p. 1113 - 1121
(2020/04/01)
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- Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
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An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.
- Hoque, Md Emdadul,Bisht, Ranjana,Haldar, Chabush,Chattopadhyay, Buddhadeb
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supporting information
p. 7745 - 7748
(2017/06/21)
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- Pyridine -2,3-di-carboxylic acid ethyl ester preparation method
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The invention discloses a preparation method of diethylpyridine-2,3-dicarboxylate. The preparation method comprises the step that propargylamine and diethyl acetylenedicarboxylate, which are taken as raw materials, react in an organic solvent with hydrogen peroxide as an oxidizing agent, thus finally obtaining diethylpyridine-2,3-dicarboxylate, wherein the reaction temperature is 60-70 DEG C; the reaction time is 11-13 hours; the mole ratio of propargylamine to diethyl acetylenedicarboxylate to hydrogen peroxide is 1 to 1 to (1.4-1.6); the organic solvent is ethanol. Diethylpyridine-2,3-dicarboxylate prepared by adopting the method has the technical advantages of high yield, low production cost, low environmental pollution, and the like.
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Paragraph 0026; 0027
(2016/10/31)
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- Rilyazine Derivatives and Compositions for The Treatment of Cancer
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The present application discloses Rilyazine analogs, methods for their preparation, and the treatment of cancer by the administration of an effective amount of the Rilyazine analogs to a patient in need thereof.
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- Remote electronic control in the regioselective reduction of succinimides: A practical, scalable synthesis of EP4 antagonist MF-310
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(Chemical Equation Presented) A practical large-scale chromatography-free synthesis of EP4 antagonist MF-310, a potential new treatment for chronic inflammation, is presented. The synthetic route provided MF-310 as its sodium salt in 10 steps and 17% overall yield from commercially available pyridine dicarboxylate 7. The key features of this sequence include a unique regioselective reduction of succinimide 2 controlled by the electronic properties of a remote pyridine ring, preparation of cyclopropane carboxylic acid 3 via a Corey - Chaykovsky cyclopropanation, and a short synthesis of sulfonamide 5. 2009 American Chemical Society.
- Molinaro, Carmela,Gauvreau, Danny,Hughes, Gregory,Lau, Stephen,Lauzon, Sophie,Angelaud, Remy,O'Shea, Paul D.,Janey, Jacob,Palucki, Michael,Hoerrner, Scott R.,Raab, Conrad E.,Sidler, Rick R.,Belley, Michel,Han, Yongxin
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supporting information; experimental part
p. 6863 - 6866
(2009/12/30)
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- QUINOLINE DERIVATIVES AS EP4 ANTAGONISTS
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The invention is directed to quinoline derivatives as prostaglandin E type receptor antagonists useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, osteoarthritis, rheumatoid arthritis and cancer. The derivatives have the following structure of formula (I): wherein A and B represents either a nitrogen atom or a CH group with the proviso that they cannot both simultaneously be CH, Q can represent a nitrogen or a carbon atom, and Y and Z are either a nitrogen atom., a N(O) group or a C(R5) group. Pharmaceutical compositions comprising the derivatives of formula (I) are also included.
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Page/Page column 31-32
(2008/06/13)
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- Process for the preparation of pyridine dicarboxylate derivatives
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There is provided a single vessel process for the preparation of a pyridine dicarboxylate compound of formula I STR1 via the sequential condensation of an alkyl vinyl ether with Vilsmeier reagent, oxalacetate and an ammonia source.
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- The preparation of pyridinecarboxylates from chloropyridines by the palladium-catalyzed alkoxycarbonylation
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The preparation of pyridinecarboxylates and pyridinedicarboxylates by alkoxycarbonylation of chloropyridines with carbon monoxide in the presence of palladium acetate and 1,1'-bis(diphenylphosphino)ferrocene is described. The process uses readily available starting materials and affords pyridinecarboxylates in good to very good yields.
- Bessard, Yves,Crettaz, Roger
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p. 2589 - 2602
(2007/10/03)
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- Synthesis of 2-Aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one and 2-Aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one
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A variety of 2-aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one and 2-aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one were prepared. The absolute configuration of the chiral centers were studied thoroughly from which the structural and stereoformulea of these compounds were deduced by using nmr and microanalysis technique.
- Makki, Mohamad S. I.,Samarkandy, Abdul-Rahim A.,Kabuli, Rida A.,Hewlins, M. J. E.
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- Antihypertensive benzopyran derivatives
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Disclosed herein are novel benzopyrans having pharmacological activity, to a process for preparing them, to pharmaceutical compositions containing them, and to their use in the treatment of hypertension.
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- Process for preparing pyridine-2,3-dicarboxylic acid compounds
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Improved process for preparing pyridine-2,3-dicarboxylic acid compounds of the formula: STR1 wherein R1 and R3 are each H, (un)substituted alkyl, or (un)substituted phenyl; R2 is H, (un)substituted alkyl, (un)substituted phenyl, alkylthio, alkoxy, (un)substituted phenylthio, (un)substituted phenoxy, halogen, alkoxycarbonyl, aminocarbonyl which may optionally be substituted, or cyano; or both of R1 and R2 or both R2 and R3 may combined together to form a divalent alkylene; and R4 and R5 are each alkyl which are useful as an intermediate for preparing herbicidally effective compounds, which comprises reacting an enone (II) and an aminodiester (III) of the formulae: STR2
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- Pyridine derivatives and their herbicidal compositions
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A pyridine derivative having the formula: STR1 wherein one of A, B, D and E is oxygen, sulfur, --SO--, --SO2 --, --NR3 --, STR2 or =CH-- with the rest being all carbon atoms; X is halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkyl, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 haloalkylthio, C1 -C4 alkoxycarbonyl, C1 -C4 alkylthioalkyl, tetrahydrothiopyranyl, hydroxyl, CF3, phenyl or pyridyl; n is an integer of from 0 to 6,; W is oxygen or sulfur; R is hydrogen, di-lower alkylimino, C1 -C5 alkyl, C2 -C5 alkenyl, C2 -C5 alkynyl, C4 or C5 oxacycloalkyl, C2 -C5 mono-, di- or tri-haloalkenyl, C2 -C5 haloalkynyl, glycidyl, furfuryl, alkylthioalkyl, C3 -C6 cycloalkyl or a cation R1 is C1 -C4 alkyl, R2 is C1 -C4 alkyl or C3 -C6 cycloalkyl, or R1 and R2 together with the ajacent carbon atom, form C3 -C6 cycloalkyl; and R3 is hydrogen or C1 -C3 alkyl. The compounds are used as herbicides.
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