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Molecules, Volume 11, Issue 2 (February-March 2006) – 9 articles , Pages 130-211

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Research

48 KiB  
Article
A Simple Synthetic Route to Methyl 3-Fluoropyridine-4-carboxylate by Nucleophilic Aromatic Substitution
by Freddy Tjosaas and Anne Fiksdahl
Molecules 2006, 11(2), 130-133; https://doi.org/10.3390/11020130 - 25 Feb 2006
Cited by 16 | Viewed by 9787
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The nitro group of methyl 3-nitropyridine-4-carboxylate (1) has successfully been replaced by fluoride anion via nucleophilic aromatic substitution to give the 3-fluoro- pyridine-4-carboxylate 2.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
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113 KiB  
Article
Synthesis and Antimicrobial Activity of Some Derivatives on the Basis (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic Acid Hydrazide
by Milan Cacic, Mladen Trkovnik, Frane Cacic and Elizabeth Has-Schon
Molecules 2006, 11(2), 134-147; https://doi.org/10.3390/11010134 - 07 Mar 2006
Cited by 114 | Viewed by 15842
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), acetic [...] 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
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46 KiB  
Article
Synthesis and Antidepressant Evaluation of Three para-Benzoquinone Mono-oximes and Their Oxy Derivatives
by Damião Pergentino De Sousa, Renata Rabelo Schefer, Ursula Brocksom and Timothy John Brocksom
Molecules 2006, 11(2), 148-155; https://doi.org/10.3390/11020148 - 10 Mar 2006
Cited by 31 | Viewed by 8664
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. Full article
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156 KiB  
Communication
Dechlorophyllation by Electrocoagulation
by Kanlaya Jumpatong, Weerachai Phutdhawong and Duang Buddhasukh
Molecules 2006, 11(2), 156-162; https://doi.org/10.3390/11020156 - 17 Mar 2006
Cited by 10 | Viewed by 7877
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 those [...] 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
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143 KiB  
Article
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
by Yonglian Zhang and Hong-Chang Liang
Molecules 2006, 11(2), 163-168; https://doi.org/10.3390/11020163 - 14 Feb 2006
Cited by 1 | Viewed by 8111
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
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253 KiB  
Article
Synthesis and Molecular Structure of 6-Amino-3-benzylmercapto-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one
by Long-Chih Hwang, Chun-Hsie Tu, Jung-Hui Wang and Gene-Hsiang Lee
Molecules 2006, 11(2), 169-176; https://doi.org/10.3390/11020169 - 17 Mar 2006
Cited by 11 | Viewed by 10471
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. The [...] 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
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155 KiB  
Article
Synthesis of New Chiral Amines with a Cyclic 1,2-Diacetal Skeleton Derived from (2R, 3R)-(+)-Tartaric Acid
by M. Teresa Barros and Ana Maria Faísca Phillips
Molecules 2006, 11(2), 177-196; https://doi.org/10.3390/11020177 - 17 Mar 2006
Cited by 8 | Viewed by 10498
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 form [...] 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
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100 KiB  
Article
L-Proline Catalyzed Michael Additions of Thiophenols to α,β-Unsaturated Compounds, Particularly α-Enones, in the Ionic Liquid [bmim]PF6
by Peter Kotrusz and Stefan Toma
Molecules 2006, 11(2), 197-205; https://doi.org/10.3390/11020197 - 17 Mar 2006
Cited by 64 | Viewed by 10074
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
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66 KiB  
Communication
Synthesis and Spectroscopic Studies of New Schiff Bases
by Hamid Latif Siddiqui, Amjid Iqbal, Saeed Ahmad and W. Weaver
Molecules 2006, 11(2), 206-211; https://doi.org/10.3390/11020206 - 17 Mar 2006
Cited by 96 | Viewed by 13763
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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