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Molecules, Volume 11, Issue 2 (February - March 2006), Pages 130-211

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Research

Open AccessArticle A Simple Synthetic Route to Methyl 3-Fluoropyridine-4-carboxylate by Nucleophilic Aromatic Substitution
Molecules 2006, 11(2), 130-133; doi:10.3390/11020130
Received: 25 January 2006 / Accepted: 24 February 2006 / Published: 25 February 2006
Cited by 7 | PDF Full-text (48 KB) | HTML Full-text | XML Full-text
Abstract The nitro group of methyl 3-nitropyridine-4-carboxylate (1) has successfully been replaced by fluoride anion via nucleophilic aromatic substitution to give the 3-fluoro- pyridine-4-carboxylate 2. Full article
Open AccessArticle Synthesis and Antimicrobial Activity of Some Derivatives on the Basis (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic Acid Hydrazide
Molecules 2006, 11(2), 134-147; doi:10.3390/11010134
Received: 31 January 2006 / Accepted: 3 March 2006 / Published: 7 March 2006
Cited by 54 | PDF Full-text (113 KB) | HTML Full-text | XML Full-text
Abstract
(7-Hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide (2) was prepared from (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester (1) and 100% hydrazine hydrate. Compound 2, is the key intermediate for the synthesis of several series of new compounds such as Schiff’s bases 3a-l, formic acid N'-[2-(7-hydroxy-2-oxo-2H- chromen-4-yl)acetyl] hydrazide (4), [...] Read more.
(7-Hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide (2) was prepared from (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester (1) and 100% hydrazine hydrate. Compound 2, is the key intermediate for the synthesis of several series of new compounds such as Schiff’s bases 3a-l, formic acid N'-[2-(7-hydroxy-2-oxo-2H- chromen-4-yl)acetyl] hydrazide (4), acetic acid N'-[2-(7-hydroxy-2-oxo-2H-chromen-4- yl)-acetyl] hydrazide (5), (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid N'-[2-(4- hydroxy-2-oxo-2H-chromen-3-yl)-2-oxoethyl] hydrazide (6), 4-phenyl-1-(7-hydroxy-2- oxo-2H-chromen- 4-acetyl) thiosemicarbazide (7), ethyl 3-{2-[2-(7-hydroxy-2-oxo-2H- chromen-4-yl)-acetyl]hydrazono}butanoate (8), (7-hydroxy-2-oxo-2H-chromen-4-yl)- acetic acid N'-[(4-trifluoromethylphenylimino)methyl] hydrazide (9) and (7-hydroxy-2- oxo-2H-chromen-4-yl)acetic acid N'-[(2,3,4-trifluorophenylimino)-methyl] hydrazide (10). Cyclo- condensation of compound 2 with pentane-2,4-dione gave 4-[2-(3,5- dimethyl-1H-pyrazol-1-yl)-2-oxoethyl]-7-hydroxy-2H-chromen-2-one (11), while with carbon disulfide it afforded 7-hydroxy-4-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-2H- chromen-2-one (12) and with potassium isothiocyanate it gave 7-hydroxy-4-[(5- mercapto-4H-1,2,4-triazol-3-yl)methyl]-2H-chromen-2-one (14). Compound 7 was cyclized to afford 2-(7-hydroxy-2-oxo-2H-chromen-4-yl)-N ́-(4-oxo-2-phenylimino- thiazolidin-3-yl) acetamide (15). Full article
Open AccessArticle Synthesis and Antidepressant Evaluation of Three para-Benzoquinone Mono-oximes and Their Oxy Derivatives
Molecules 2006, 11(2), 148-155; doi:10.3390/11020148
Received: 18 January 2006 / Accepted: 7 March 2006 / Published: 10 March 2006
Cited by 20 | PDF Full-text (46 KB) | HTML Full-text | XML Full-text
Abstract
A series of three para-benzoquinone mono-oximes and four oxy-derivatives were prepared and tested for their antidepressant properties. The (4E) oxime of 2-isopropyl-5- methyl-para-benzoquinone (4) and the corresponding 2-diethylamino-ethyl derivative (10) present antidepressant activities and were slightly more potent than the reference standard. [...] Read more.
A series of three para-benzoquinone mono-oximes and four oxy-derivatives were prepared and tested for their antidepressant properties. The (4E) oxime of 2-isopropyl-5- methyl-para-benzoquinone (4) and the corresponding 2-diethylamino-ethyl derivative (10) present antidepressant activities and were slightly more potent than the reference standard. Full article
Open AccessCommunication Dechlorophyllation by Electrocoagulation
Molecules 2006, 11(2), 156-162; doi:10.3390/11020156
Received: 18 January 2006 / Revised: 15 March 2006 / Accepted: 16 March 2006 / Published: 17 March 2006
Cited by 4 | PDF Full-text (156 KB) | HTML Full-text | XML Full-text
Abstract
Electrocoagulation was used for dechlorophyllation of alcoholic extracts from five plants. The results showed that for every plant extract studied, electrocoagulation was more efficient than the classical solvent extraction method in removing plant pigments, while not affecting the important secondary metabolites in [...] Read more.
Electrocoagulation was used for dechlorophyllation of alcoholic extracts from five plants. The results showed that for every plant extract studied, electrocoagulation was more efficient than the classical solvent extraction method in removing plant pigments, while not affecting the important secondary metabolites in those extracts. Full article
Open AccessArticle Synthesis and Structural Characterization of the Sodium Salt of a New Sulfonate-containing Water Soluble N-Donor Ligand⎯ Self-assembly in the Solid State by π−π Stacking Interactions
Molecules 2006, 11(2), 163-168; doi:10.3390/11020163
Received: 1 September 2005 / Revised: 14 February 2006 / Accepted: 14 February 2006 / Published: 14 February 2006
Cited by 1 | PDF Full-text (143 KB) | HTML Full-text | XML Full-text
Abstract
The synthesis, spectroscopic characterization, and X-ray crystal structure ofthe sodium salt of a new sulfonated water-soluble ligand, sodium 2-(2-pyridin-2-yl-ethylamino)-benzenesulfonate (L) are described. Compound L crystallizes in thecentrosymmetric space group Pbcn, orthorhombic, a=31.930(13) å, b=7.153(3) å,c=14.193(6) å, α=90.00, β=90.00, γ=90.00, V=3220(2) å3 [...] Read more.
The synthesis, spectroscopic characterization, and X-ray crystal structure ofthe sodium salt of a new sulfonated water-soluble ligand, sodium 2-(2-pyridin-2-yl-ethylamino)-benzenesulfonate (L) are described. Compound L crystallizes in thecentrosymmetric space group Pbcn, orthorhombic, a=31.930(13) å, b=7.153(3) å,c=14.193(6) å, α=90.00, β=90.00, γ=90.00, V=3220(2) å3, Z=9. π−π stacking contactsinvolving interactions between the π-donor benzene and the π-acceptor pyridine systemsreinforce and direct the self-assembly of the structural motifs in the solid state. Full article
Open AccessArticle Synthesis and Molecular Structure of 6-Amino-3-benzylmercapto-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one
Molecules 2006, 11(2), 169-176; doi:10.3390/11020169
Received: 5 November 2005 / Revised: 10 March 2006 / Accepted: 10 March 2006 / Published: 17 March 2006
Cited by 7 | PDF Full-text (253 KB) | HTML Full-text | XML Full-text
Abstract
The title compound 6-amino-3-benzylmercapto-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one (4), molecular formula C11H10N6OS, was obtained by the reaction of3-amino-2-benzyl-6-hydrazino-1,2,4-triazin-5(2H)-one (3) with carbon disulfide in awater/pyridine mixture. Compound 4 can also be synthesized by reacting6-amino-3(2H)mercapto-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (7) with benzylbromide in methanolic ammonia water. [...] Read more.
The title compound 6-amino-3-benzylmercapto-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one (4), molecular formula C11H10N6OS, was obtained by the reaction of3-amino-2-benzyl-6-hydrazino-1,2,4-triazin-5(2H)-one (3) with carbon disulfide in awater/pyridine mixture. Compound 4 can also be synthesized by reacting6-amino-3(2H)mercapto-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (7) with benzylbromide in methanolic ammonia water. The compound crystallizes in the monoclinicspace group P21/c with a = 7.2926(15), b = 14.456(2), c = 11.436(2) å, β = 105.30(2)°, V= 1162.9(4) å3 and Z = 4, resulting in a density Dcalc of 1.567 g/cm3. Molecules of 4 arelinked by extensive intermolecular N-H···N and N-H···O hydrogen bonding [graph set R22 (9)]. The structure is further stabilized by π-π stacking interactions. 2 Full article
Open AccessArticle Synthesis of New Chiral Amines with a Cyclic 1,2-Diacetal Skeleton Derived from (2R, 3R)-(+)-Tartaric Acid
Molecules 2006, 11(2), 177-196; doi:10.3390/11020177
Received: 27 January 2006 / Revised: 15 March 2006 / Accepted: 16 March 2006 / Published: 17 March 2006
Cited by 7 | PDF Full-text (155 KB) | HTML Full-text | XML Full-text
Abstract
The syntheses of new chiral cyclic 1,2-diacetals from (2R, 3R)-( )-tartaric acidare described. C2-symmetrical diamines were prepared via direct amidation of the tartrate orfrom the corresponding bismesylate via reaction with sodium azide. For C1-symmetricalcompounds, the Appel reaction was used to [...] Read more.
The syntheses of new chiral cyclic 1,2-diacetals from (2R, 3R)-( )-tartaric acidare described. C2-symmetrical diamines were prepared via direct amidation of the tartrate orfrom the corresponding bismesylate via reaction with sodium azide. For C1-symmetricalcompounds, the Appel reaction was used to form the key intermediate, amonochlorocarbinol, from the diol. Some of the new chiral compounds, produced in good tohigh yields, may be potentially useful as asymmetric organocatalysts or as nitrogen andsulfur chelating ligands for asymmetric metal catalyzed reactions. Thus, a bis-N-methyl-methanamine derivative, used in substoichiometric amounts, was found to catalyze theenantioselective addition of cyclohexanone to (E)-β-nitrostyrene with highdiastereoselectivity (syn / anti = 92:8), albeit giving moderate optical purity (syn: 30 %). Full article
Open AccessArticle L-Proline Catalyzed Michael Additions of Thiophenols to α,β-Unsaturated Compounds, Particularly α-Enones, in the Ionic Liquid [bmim]PF6
Molecules 2006, 11(2), 197-205; doi:10.3390/11020197
Received: 23 November 2005 / Revised: 8 March 2006 / Accepted: 15 March 2006 / Published: 17 March 2006
Cited by 47 | PDF Full-text (100 KB) | HTML Full-text | XML Full-text
Abstract L-Proline catalyzed additions of 13 different thiols to 11 different α-enoneMichael acceptors in [bmim] PF6 are reported. Reasonable to high yields of the reactionproducts were isolated in most cases. Full article
Open AccessCommunication Synthesis and Spectroscopic Studies of New Schiff Bases
Molecules 2006, 11(2), 206-211; doi:10.3390/11020206
Received: 2 August 2005 / Revised: 10 March 2006 / Accepted: 10 March 2006 / Published: 17 March 2006
Cited by 49 | PDF Full-text (66 KB) | HTML Full-text | XML Full-text
Abstract Five novel Schiff bases have been prepared from o-formylphenoxyacetic acidand a series of aminothiazoles to form a number of potentially biologically activecompounds. The structures of these Schiff bases have been characterized using IR and 1H-and 13C-NMR spectroscopy. Full article

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