New potential calcium channel modulators: design and synthesis of compounds containing two pyridine, pyrimidine, pyridone, quinoline and acridine units under microwave irradiation

Tu, Shu‐Jiang; Miao, Chun‐Bao; Fang, Fang; Ye, Feng; Li, Tuanjie; Zhuang, Qiya; Zhang, Xiaojing; Zhu, Shaolin; Shi, Daqing

doi:10.1016/j.bmcl.2003.12.092

Cited by 57 publications

(12 citation statements)

References 34 publications

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“…One-pot cyclocondensation of aldehyde, b-ketoester, and urea, known as Biginelli reaction (Scheme 1) [4], is a very useful MCR to access multifunctionalized 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs). DHPMs represent a heterocyclic system of remarkable pharmacological and therapeutic properties such as antiviral, antibacterial, and antitumor [5][6][7]. Several alkaloids-derivate DHPMs possessing biological and anti-HIV characters have been isolated from marine sources [8][9][10].…”

mentioning

confidence: 99%

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Lu¹,

Chen²,

Zhang³

et al. 2011

Int J of Quantum Chemistry

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In this study, enantioselective Biginelli reaction of aldehyde, b-ketoester, and urea catalyzed by natural (2R, 3R)-tartaric acid has been investigated using density functional theory calculations. The results indicate that the most favorable pathway involves a protonated imine from aldehyde and urea in the first step. Tartaric acid forms H-bonds network with substrates enhancing the electrophilicity of protonated imine and the nucleophilicity of b-ketoester. (R)-3,4-Dihydropyrimidin-2-(1H)-ones is preferable for the reaction. The solvent effect is discussed in the prediction of enantiomeric excess (ee) values in ethanol and water.

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confidence: 99%

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Lu¹,

Chen²,

Zhang³

et al. 2011

Int J of Quantum Chemistry

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“…78,81 The N-hydroxyacridine 170 78,90 (R=OH) has been synthesized by using hydroxylamine instead of ammonium acetate ( Figure 22). …”

Section: Figure 21mentioning

confidence: 99%

“…[81][82][83][84][85] or using silica-supported tin chloride and titanium tetrachloride as catalyst 93 (Scheme 58).…”

Section: Figure 22mentioning

confidence: 99%

Synthesis of 1,4-phenylene bridged bis-heterocyclic compounds

Shaker¹

2011

Arkivoc

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“…It exhibits diverse pharmacological properties, such as antiviral, antitumor, antibacterial and antiinflammatory activities [1,2]. Hexahydropyrimidine derivatives are also used as valuable reagents in organic synthesis [3,4].…”

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confidence: 99%

Complexation to Cadmium(II) of a Tetradentate Ligand Resulting from the Condensation of 2-Pyridinecarbaldehyde with N-(2- Aminoethyl)propane-1,3-diamine

Hakimi

Mardani

Moeini

et al. 2013

Zeitschrift Für Naturforschung B

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The reaction of 2-pyridinecarbaldehyde with N-(2-aminoethyl)propane-1,3-diamine in a 2 : 1 molar ratio under microwave irradiation gave 2-(2-(pyridin-2-yl)-tetrahydropyrimidin-1(2H)-yl)-N-(pyridin-2-ylmethylene)ethanamine (L) as a mixture with the isomer 3-(2-(pyridin-2-yl)imidazolidin-1-yl)-N-(pyridin-2-ylmethylene)propan-1-amine (L * ). The molecules were characterized by elemental analyses and spectroscopic methods. Percentages of L and L * were evaluated through integration of selected 1 H NMR signals. The cadmium iodide complex of L, [Cd(L)I 2 ]·H 2 O (1), was prepared and identified by elemental analysis, FT-IR, Raman, and 1 H NMR spectroscopy, and single-crystal X-ray diffraction. In the crystal structure of 1 the cadmium atom with four coordinated nitrogen atoms and two iodide ions has a distorted octahedral geometry. A water molecule is also incorporated in the crystal network. Several hydrogen bonds including N-H···O, C-H···O, C-H···I, and O-H···I interactions are present in the crystal structure of 1.

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New potential calcium channel modulators: design and synthesis of compounds containing two pyridine, pyrimidine, pyridone, quinoline and acridine units under microwave irradiation

Cited by 57 publications

References 34 publications

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Synthesis of 1,4-phenylene bridged bis-heterocyclic compounds

Complexation to Cadmium(II) of a Tetradentate Ligand Resulting from the Condensation of 2-Pyridinecarbaldehyde with N-(2- Aminoethyl)propane-1,3-diamine

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