Interaction of 1-Benzyl-4-benzoyl-5-phenyl-2,3-dihydro-2,3-pyrroledione with Ketene Diethylacetal: Synthesis and Crystal and Molecular Structure of 1-Benzyl-4-benzoyl-3-hydroxy-5-phenyl-5-ethoxycarbonylmethyl-2,5-dihydro-2-pyrrolone

1-Benzyl-4-benzoyl-5-phenyl-2,3-dihydro-2,3-pyrroledione reacts with ketene diethylacetal, forming 1-benzyl-4-benzoyl-3-hydroxy-5-phenyl-5-ethoxycarbonylmethyl-2,5-dihydro-2-pyrrolone, whose crystal and molecular structure was studied by XRD.     

Interaction of 4,5-diphenyl-2,3-dihydro-2,3-pyrroledione with ethoxycarbonylmethylenetriphenylphosphorane: synthesis and crystal structure of 4,5-diphenyl-Z-2-ethoxycarbonylmethylene-2,3-dihydro-3-pyrrolone

1-Unsubstituted 4,5-diphenyl-2,3-dihydro-2,3-pyrroledione interacts with ethoxycarbonyl-methylenetriphenylphosphorane regioselectively to give 4,5-diphenyl-Z-2-ethoxycarbonyl-methylene-2,3-dihydro-3-pyrrolone. The crystal and molecular structure of the latter was studied by X-ray analysis.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1556–1558, August, 1995.     

Synthesis and Characterization of Novel 2-(1,2,3-Triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles and 2-(4,5-Dihydro-1H-pyrazol-1-yl)-4-(1H-1,2,3-triazol-4-yl)thiazoles

Reactions of 1-(5-methyl)-1H-1,2,3-triazol-4-yl)ethan-1-ones and benzaldehydes in ethanol under basic conditions gave the corresponding chalcones. Reactions of the chalcones combined with thiosemicarbazide in dry ethanol containing sodium hydroxide afforded the corresponding pyrazolin-N-thioamides. Reactions of the synthesized pyrazolin-N-thioamides and several ketones (namely, ethyl 2-chloro-3-oxobutanoate, 2-bromoacetylbenzofuran, and hydrazonoyl chloride) gave the corresponding novel 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles in high yields (77–90%). Additionally, 2-(4,5-dihydro-1H-pyrazol-1-yl)-4-(1H-1,2,3-triazol-4-yl)thiazoles were obtained in high yields (84–87%) from reactions with N-pyrazoline-thioamides and 4-bromoacetyl-1,2,3-triazoles under basic conditions. The structures of six of the newly synthesized heterocycles were confirmed by X-ray crystallography.     

Chemistry of 2-methylene-2,3-dihydro-3-furanones

[3+2]-Cycloaddition of 2-methoxycarbonylmethylene-5-phenyl-2,3-dihydro-3-furanone to acetone azine has been studied. This results in a monospirocycloadduct,viz., 9,9-dimethyl-6-methoxycarbonyl-2-phenyl-1-oxa-7,8-diazaspiro[4.4]nona-2,6-dien-4-one. Its structure has been confirmed by X-ray diffraction analysis.For the previous communication see Ref. 1.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 306–308, February, 1994.     

Interaction of 5-aryl-4-quinoxalinyl-2,3-dihydro-2,3-furandiones with mesitylamine and methyl(phenyl)hydrazine. Synthesis and crystal and molecular structure of 2-(1-mesityl-4,5-dioxo-2-phenyl-4,5-dihydro-3-pyrollyl)-3-phenylquinoxaline

The interaction of 5-aryl-4-quinoxaline-2,3-dihydro-2,3-furandiones with mesitylamine and methyl(phenyl) hydrazine results in the formation of 1-substituted 5-aryl-4-quinoxalinyl-2,3-dihydro-2,3-pyrrolediones. The crystal and molecular structure of the 1-mesityl-5-phenyl derivative was investigated by X-ray diffraction.Original Russian Text Copyright © 2004 by Z. G. Aliev, N. Yu. Lisovenko, L. O. Atovmyan, and A. N. MaslivetzTranslated from Zhurnal Strukturnoi Khimii, Vol. 45, No. 3, pp. 553–557, May–June 2004.     

New Heterocyclic Phosphorus Ylides: Synthesis,Crystal Structure,and Theoretical Calculation of Alkyl Substituted 3-(4-Benzoyl-1,5-diphenyl-2,3-dihydro-1H-pyrazol-3-yl)-3-oxo-2-(triphenylphosphoranylidene) Propanoates

Novel alkyl substituted 3-(4-benzoyl-1,5-diphenyl-2,3-dihydro-1H-pyrazol-3-yl)-3-oxo-2-(triphenylphosphoranylidene) propanoates (3) were synthesized from 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carbonylchloride (1) and alkyl (triphenylphosphoranylidene) acetates (2a–b). The synthesized compounds were characterized by elemental analysis, spectroscopic studies (3a–b), and single crystal X-ray diffraction (3a). The mechanism of the reaction between (1) and (2a) was studied by AM1, and the geometrical parameters of the studied molecules were also carried out in B3LYP methods with the standard 6–31G (d,p) basis set. NBO analysis were studied for 1 and 2a B3LYP methods with the standard 6–31G (d,p) basis set.     

Design,synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives(aurones, 1–20) were synthesized and screened for their inhibitory activity against h MAO. Seventeen compounds(1–5, 7–17,19) were found to be selective towards h MAO-B, while two were non-selective(6 and 20) and one(18)selective towards h MAO-A. Compound 17(Ki = 0.10 0.01 mmol/L) was found to be equally potent and selective towards h MAO-B, when compared with the standard drug Selegiline(Ki = 0.12 0.01 mmol/L).Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences h MAO-B inhibitory potency, while their structural bulkiness influences selectivity between h MAO-A and h MAO-B.Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity.     

Unexpected synthesis of 6-amino-2,3-dihydro-4-pyrone-3-spirocyclohexane

The reaction of 2-amino-2-(trichloromethyl)tetrahydro-4-pyrone-5-spirocyclohexane with ethylenediamine afforded 6-amino-2,3-dihydro-4-pyrone-3-spirocyclohexane, whereas 2-amino-5,5-dimethyl-2-(trichloromethyl)tetrahydro-4-pyrone gave 2-(3-hydroxy-2,2-dimethylpropionylmethylene)imidazolidine in low yield.     

Synthesis and Crystal Structure of a New Quinazolinone Compound 2,3-Dihydro-2-（2-hydroxyphenyl）-3-phenyl-quinazolin-4（1H）-one

A new quinazolinone compound 2,3-dihydro-2-(2-hydroxyphenyl)-3-phenylquinazolin-4(IH)-one 3 ([C2oH16O2N2]-C2H5OH, Mr = 362.42) and compound 2-(2-hydroxybenzylidene-amino)-N-phenyl-benzamide 2 (C2oH16O2N2, Mr = 316.34) were prepared from a precursor of 2-amino-N-phenyl-benzamide 1 (C13H12ON2, Mr = 212.25). Compound 3 was characterized by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic,space group Pbca with a = 1.2889(11), b = 1.6170(14), c = 1.7729(15) nm, V= 3.695(6) nm^3, Z= 8, F(000) = 1536, Mr = 362.42, Dc = 1.303 g/cm^3, μ(MoKa) = 0.087 mm^-1, R = 0.0447 and wR= 0.0879. The crystal structure analysis indicates that the title compound has a two-dimensional network structure formed by hydrogen bonds and electrostatic interactions.     

Facile Iodine(III)-Mediated Approach for the Regioselective Chlorination of 2-Aryl-2,3-dihydro-4(1H)-quinolones

Oxidation of 2-aryl-2,3-dihydro-4(1H)-quinolones (1) with 1.5 equivalents of (dichloroiodo)benzene in dichloromethane at room temperature leads to regioselective chlorination, thereby offering an efficient method for the synthesis of new 2-aryl-6-chloro-2,3-dihydro-4(1H)-quinolones (3).     

A versatile approach for the asymmetric synthesis of 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones

Based on the use of (R)-p-benzyloxyphenylglycinol (10) as a new oxidatively cleavable chiral auxiliary, a flexible approach to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones via a diastereoselective reductive-alkylation is developed. The oxidative cleavage of the chiral auxiliary by CAN under mild conditions ensured the access to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones with ee at least 92%.     

Thermal rearrangement of condensed alkoxy-substituted 2-trifluoromethyl-4H-pyran-4-ones to spiroannelated 3(2H)-furanones

Isomerization of the acetates and benzoates of condensed hydroxy-substituted 2-trifluoromethyl-4H-pyran-4-ones at 300–320°C gave the corresponding derivatives of spiroannelated 3(2H)-furanones. Their structure was confirmed by spectral data and by X-ray crystallographic analysis.Belarus State University, Minsk; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1028–1034, August, 2000.     

Synthesis of 5-[2-(Phenoxy)ethyl] Derivatives of 6-Methyluracil, 6-Methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one,and 2-Imino-6-methyl-2,3-dihydro-1H-pyrimidin-4-one

A synthesis of novel derivatives of 6-methyluracil, 6-methyl-2-thioxo-, and 2-imino-6-methyl-2,3-dihydro-1H-pyrimidin-4-one containing a 2-(phenoxy)ethyl substituent at position 5 of the pyrimidine ring has been carried out. It was found that 5-[2-(phenoxy)ethyl] derivatives of 6-methyl-2-thioxo- and 2-imino-6-methyl-2,3-dihydro-1H-pyrimidin-4-one are obtained by the condensation of the corresponding ethyl 3-oxo-2-(2-phenoxyethyl)butanoates with thiourea or guanidine. 6-Methyl-5-[2-(phenoxy)ethyl]uracils can be prepared by treating 6-methyl-5-[2-(phenoxy)ethyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-ones with an excess of aqueous monochloroacetic acid solution. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1213–1217, August, 2005.