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Molecules, Volume 10, Issue 2 (February 2005) – 22 articles , Pages 318-515

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Article
Microwave-Assisted Amination of a Chloropurine Derivative in the Synthesis of Acyclic Nucleoside Analogues
Molecules 2005, 10(2), 508-515; https://doi.org/10.3390/10020508 - 28 Feb 2005
Cited by 17 | Viewed by 6170
Abstract
An efficient protocol for the amination of 6-chloropurine derivatives through nucleophilic aromatic substitution under microwave irradiation was developed and applied to the synthesis in two steps of a series of new acyclic nucleosides (acyclovir analogues) starting from commercially available compounds. Full article
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Review
Reaction of Nitrilimines and Nitrile Oxides with Hydrazines, Hydrazones and Oximes
Molecules 2005, 10(2), 492-507; https://doi.org/10.3390/10020492 - 28 Feb 2005
Cited by 24 | Viewed by 7997
Abstract
This review article discusses the reaction of nitrilimines and nitrile oxides with hydrazines, hydrazones, and oximes. Three reaction modes were observed. The article mainly covers our work published over the last fifteen years, in which interesting heterocyles such as oxadiazoles, triazoles, and tetrazines [...] Read more.
This review article discusses the reaction of nitrilimines and nitrile oxides with hydrazines, hydrazones, and oximes. Three reaction modes were observed. The article mainly covers our work published over the last fifteen years, in which interesting heterocyles such as oxadiazoles, triazoles, and tetrazines were synthesized and fully characterized. Full article
Article
A General Synthesis of Tris-Indole Derivatives as Potential Iron Chelators
Molecules 2005, 10(2), 488-491; https://doi.org/10.3390/10020488 - 28 Feb 2005
Cited by 3 | Viewed by 5052
Abstract
The development of a novel route for the synthesis of a new class of compounds is described. The first tripodal, tris-indole amines are prepared by straightforward routes. Full article
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Article
A Novel Approach in Cinnamic Acid Synthesis: Direct Synthesis of Cinnamic Acids from Aromatic Aldehydes and Aliphatic Carboxylic Acids in the Presence of Boron Tribromide
Molecules 2005, 10(2), 481-487; https://doi.org/10.3390/10020481 - 28 Feb 2005
Cited by 25 | Viewed by 10017
Abstract
Cinnamic acids have been prepared in moderate to high yields by a new direct synthesis using aromatic aldehydes and aliphatic carboxylic acids, in the presence of boron tribromide as reagent, 4-dimethylaminopyridine (4-DMAP) and pyridine (Py) as bases and N-methyl-2-pyrolidinone (NMP) as solvent, at [...] Read more.
Cinnamic acids have been prepared in moderate to high yields by a new direct synthesis using aromatic aldehydes and aliphatic carboxylic acids, in the presence of boron tribromide as reagent, 4-dimethylaminopyridine (4-DMAP) and pyridine (Py) as bases and N-methyl-2-pyrolidinone (NMP) as solvent, at reflux (180-190°C) for 8-12 hours. Full article
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Article
5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-Furan-2yl-4H [1,2,4] triazole-3-thiol and Their Thiol-Thione Tautomerism
Molecules 2005, 10(2), 475-480; https://doi.org/10.3390/10020475 - 28 Feb 2005
Cited by 81 | Viewed by 8334
Abstract
5-Furan-2-yl[1,3,4]oxadiazole-2-thiol (Ia) and 5-furan-2-yl-4H-[1,2,4]-triazole-3-thiol (Ib) were synthesized from furan-2-carboxylic acid hydrazide. Mannich basesand methyl derivatives were then prepared. The structures of the synthesized compoundswere confirmed by elemental analyses, IR and 1H-NMR spectra. Their thiol-thione tautomericequilibrium is described. Full article
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Article
Influence of the Dielectric Medium on the Carbonyl Infrared Absorption Peak of Acetylferrocene
Molecules 2005, 10(2), 457-474; https://doi.org/10.3390/10020457 - 28 Feb 2005
Cited by 4 | Viewed by 8799
Abstract
The solvent effect on the position of the carbonyl vibrational stretching ofacetylferrocene in aprotic media was studied in this work. The solvent-induced shifts in thisorganometallic compound were interpreted in terms of the alternative reaction field model(SCRF-MO) proposed by Kolling. In contrast to the [...] Read more.
The solvent effect on the position of the carbonyl vibrational stretching ofacetylferrocene in aprotic media was studied in this work. The solvent-induced shifts in thisorganometallic compound were interpreted in terms of the alternative reaction field model(SCRF-MO) proposed by Kolling. In contrast to the established trends for carbonyl groupsin organic systems, the results suggest that the continuum models for the reaction field arenot adequate and that the influence of dipolarity-polarizability described by aninhomogeneous coupling function θ (ε ) L(n 2 ) that assumes optical dielectric saturation isresponsible for the carbonyl band shift and, there is empirical evidence that the effect offield-induced intermolecular interaction on band shift, interpreted in terms of the van derWaals forces from the solvent, have a important contribution to this phenomena. Full article
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Article
Solution-phase Synthesis of a Combinatorial Library of 3-[4-(Coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid Amides
Molecules 2005, 10(2), 444-456; https://doi.org/10.3390/10020444 - 28 Feb 2005
Cited by 26 | Viewed by 5893
Abstract
The parallel solution-phase synthesis of a new combinatorial library of 3-[4-(R1-coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides 9 has been developed. The synthesis involves two steps: 1) the synthesis of core building blocks – 3- [4-(coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acids, 6 – by the reaction of 3-(ω-bromacetyl)coumarins 1 with 3-amino(thioxo)methylcarbamoylpropanoic [...] Read more.
The parallel solution-phase synthesis of a new combinatorial library of 3-[4-(R1-coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides 9 has been developed. The synthesis involves two steps: 1) the synthesis of core building blocks – 3- [4-(coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acids, 6 – by the reaction of 3-(ω-bromacetyl)coumarins 1 with 3-amino(thioxo)methylcarbamoylpropanoic acid (5); 2) the synthesis of the corresponding 3-[4-(coumarin-3-yl)-1,3-thiazol-2-yl- carbamoyl]propanoic acids amides 9 using 1,1’-carbonyldimidazole as a coupling reagent. The advantages of the method compared to existing ones are discussed. Full article
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Article
1H- and 13C-NMR Analysis of a Series of 1,2-Diaryl-1H-4,5-dihydroimidazoles
Molecules 2005, 10(2), 435-443; https://doi.org/10.3390/10020435 - 28 Feb 2005
Cited by 8 | Viewed by 4452
Abstract
An analysis of the 1H- and 13C-NMR spectra of a series of 1,2-diaryl-1H-4,5-dihydroimidazoles and comparisons with 4,5-dihydroimidazoles having differentsubstitution patterns are presented. The influence of different 1-aryl and 2-aryl groupsubstituents on spectroscopic parameters of the heterocyclic ring and on the contributionsof [...] Read more.
An analysis of the 1H- and 13C-NMR spectra of a series of 1,2-diaryl-1H-4,5-dihydroimidazoles and comparisons with 4,5-dihydroimidazoles having differentsubstitution patterns are presented. The influence of different 1-aryl and 2-aryl groupsubstituents on spectroscopic parameters of the heterocyclic ring and on the contributionsof possible mesomeric structures in the system was determined. Spectroscopic featuresare coherent with the presence of two conjugated systems (Ar1-N and Ar2-C=N) whichcompete with the delocalization characteristics of the amidine system. Full article
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Article
The Synthesis and Herbicidal Activity of 1-Alkyl-3-(α-hydroxysubstituted benzylidene)pyrrolidine-2,4-diones
Molecules 2005, 10(2), 427-434; https://doi.org/10.3390/10020427 - 28 Feb 2005
Cited by 16 | Viewed by 7179
Abstract
In the search for better herbicides a series of 1-alkyl-3-(α-hydroxy-(un)substituted benzylidene)pyrrolidine-2,4-diones were prepared and their structure-activity relationships studied. All their structures have been confirmed by 1H-NMR andelemental analysis. The preliminary bioassay results indicated that some of them have highherbicidal activity against annual [...] Read more.
In the search for better herbicides a series of 1-alkyl-3-(α-hydroxy-(un)substituted benzylidene)pyrrolidine-2,4-diones were prepared and their structure-activity relationships studied. All their structures have been confirmed by 1H-NMR andelemental analysis. The preliminary bioassay results indicated that some of them have highherbicidal activity against annual dicotyledonous and monocotyledonous plants. Full article
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Article
Investigation of DNA-protein Sequence-Specific Interactions with a ds-DNA Array
Molecules 2005, 10(2), 417-426; https://doi.org/10.3390/10020417 - 28 Feb 2005
Cited by 5 | Viewed by 10276
Abstract
The sequence specific recognitions between DNAs and proteins play important roles in many biological functions. The use of double-stranded DNA arrays (ds-DNA arrays) for studying sequence specific recognition between DNAs and proteins is a promising method. Here we report the use of a [...] Read more.
The sequence specific recognitions between DNAs and proteins play important roles in many biological functions. The use of double-stranded DNA arrays (ds-DNA arrays) for studying sequence specific recognition between DNAs and proteins is a promising method. Here we report the use of a ds-DNA probe with multi operation sites of restriction proteins in the middle sequence to investigate DNA-protein sequence-specific interactions including methylation. We arranged EcoR I site and Rsa I site on the same duplex DNA probe to fabricate ds-DNA arrays. We used the ds-DNA arrays to study DNA-restriction enzyme reactions before and after duplex DNA methylation under different probe concentration and reaction time conditions. Our results indicated that the ds-DNA arrays can be further biochemically modified and made accessible for interactions between DNAs and proteins in complex multi-step gene-regulation processes. Full article
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Article
Synthesis and Cyclizations of N-(2,3-, 3,4- and 3,5-Dimethylphenyl)-β-alanines
Molecules 2005, 10(2), 407-416; https://doi.org/10.3390/10020407 - 28 Feb 2005
Cited by 12 | Viewed by 5039
Abstract
A series of 1-aryl substituted dihydro-, 5-methyldihydro- and 6-methyl-dihydro-2,4(1H,3H)pyrimidinediones and their 2-thio analogues were obtained byreaction of the corresponding β-alanines or α-methyl- and β-methyl-β-alanines with ureaor potassium thiocyanate. The reaction of N-(2,3- and 3,5-dimethylphenyl)-α-methyl-β-alanines with ethyl acetoacetate gave 1-(2,3- or 3,5-dimethylphenyl)-2,5-dimethyl-1,4,5,6-tetrahydro-4(1H)pyridones. The combined [...] Read more.
A series of 1-aryl substituted dihydro-, 5-methyldihydro- and 6-methyl-dihydro-2,4(1H,3H)pyrimidinediones and their 2-thio analogues were obtained byreaction of the corresponding β-alanines or α-methyl- and β-methyl-β-alanines with ureaor potassium thiocyanate. The reaction of N-(2,3- and 3,5-dimethylphenyl)-α-methyl-β-alanines with ethyl acetoacetate gave 1-(2,3- or 3,5-dimethylphenyl)-2,5-dimethyl-1,4,5,6-tetrahydro-4(1H)pyridones. The combined spectral data obtained by 1H-, 13C-,1 H/13C (HETCOR) NMR and IR provided useful information about the structure of theproducts synthesized in this work. Full article
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Article
A Comparison of Microwave-Accelerated and Conventionally Heated Iodination Reactions of Some Arenes and Heteroarenes, Using ortho-Periodic Acid as the Oxidant†
Molecules 2005, 10(2), 401-406; https://doi.org/10.3390/10020401 - 28 Feb 2005
Cited by 15 | Viewed by 6821
Abstract
A fast and simple method for the oxidative iodination of some activated arenes and heteroarenes, either under microwave irradiation or by conventional heating, is reported, using diiodine and ortho-periodic acid as the oxidant. The reactions were carried out in hot 95% ethanol under [...] Read more.
A fast and simple method for the oxidative iodination of some activated arenes and heteroarenes, either under microwave irradiation or by conventional heating, is reported, using diiodine and ortho-periodic acid as the oxidant. The reactions were carried out in hot 95% ethanol under a reflux condenser. For the microwave assisted reactions, the reaction times were always notably shortened, but the yields were nearly the same as those afforded by the conventional method. Full article
Article
An Aromatic Iodination Method, with Iodic Acid Used as the Only Iodinating Reagent
Molecules 2005, 10(2), 394-400; https://doi.org/10.3390/10020394 - 28 Feb 2005
Cited by 7 | Viewed by 6718
Abstract
Benzene, halobenzenes, and a number of more or less deactivated arenes,including nitrobenzene, readily reacted in anhydrous HIO3/AcOH/Ac2o/conc. H2SO4mixtures to probably give ArIO2 intermediates or other hypervalent species (notisolated). The final reaction mixtures were poured [...] Read more.
Benzene, halobenzenes, and a number of more or less deactivated arenes,including nitrobenzene, readily reacted in anhydrous HIO3/AcOH/Ac2o/conc. H2SO4mixtures to probably give ArIO2 intermediates or other hypervalent species (notisolated). The final reaction mixtures were poured into excess aq. Na2SO3 solution (areductant) to give the purified iodinated products in 39-83% yields. Full article
Article
Diastereoselective Synthesis of 2-Phenylselenenyl-1,3-anti-Diols and 2-Phenylselenenyl-1,3-anti-Azido-Alcohols via Hydroxyand Azido-Selenenylation Reactions
Molecules 2005, 10(2), 383-393; https://doi.org/10.3390/10020383 - 28 Feb 2005
Cited by 11 | Viewed by 6448
Abstract
A method to synthesize 2-phenylselenenyl-1,3-anti-diols and 2-phenyl- selenenyl-1,3-anti-azidoalcohols via hydroxy- or azido-selenenylation of trans-allylic alcohols is reported. Moreover, the first example of hydroxyl-selenenylation of an allylic azide is presented. Yields ranging from moderate to good and diastereomeric ratios up to 95:5 are achieved. [...] Read more.
A method to synthesize 2-phenylselenenyl-1,3-anti-diols and 2-phenyl- selenenyl-1,3-anti-azidoalcohols via hydroxy- or azido-selenenylation of trans-allylic alcohols is reported. Moreover, the first example of hydroxyl-selenenylation of an allylic azide is presented. Yields ranging from moderate to good and diastereomeric ratios up to 95:5 are achieved. Full article
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Article
Synthesis of 4-Amino-4,5-dihydro-1H-1,2,4-triazole-5-ones and their Isatin-3-imine Derivatives
Molecules 2005, 10(2), 376-382; https://doi.org/10.3390/10020376 - 28 Feb 2005
Cited by 36 | Viewed by 5678
Abstract
Iminoester hydrochlorides 1 have been synthesized. These compounds werethen converted into ester ethoxycarbonyl hydrazones 2, from which in turn a new seriesof substituted 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones, 3, was then prepared.Finally a set of isatin imine derivatives 4 was obtained from the reaction of compounds 3with [...] Read more.
Iminoester hydrochlorides 1 have been synthesized. These compounds werethen converted into ester ethoxycarbonyl hydrazones 2, from which in turn a new seriesof substituted 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones, 3, was then prepared.Finally a set of isatin imine derivatives 4 was obtained from the reaction of compounds 3with isatin. The structures of all the new synthesized compounds were confirmed byelemental analyses, IR, 1H-NMR and 13C-NMR spectra. Full article
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Article
Synthesis of Pyrrolo[2,3-d][1,2,3]thiadiazole-6-carboxylates via the Hurd-Mori Reaction. Investigating the Effect of the N-Protecting Group on the Cyclization
Molecules 2005, 10(2), 367-375; https://doi.org/10.3390/10020367 - 28 Feb 2005
Cited by 17 | Viewed by 6679
Abstract
A route to methyl pyrrolo[2,3-d][1,2,3]thiadiazole-6-carboxylates as potential plant activators and inducers of systemic acquired resistance (SAR) is reported. A synthetic strategy based on cyclization of the thiadiazole ring system utilizing thionyl chloride via the Hurd-Mori protocol as key step was developed. Success of [...] Read more.
A route to methyl pyrrolo[2,3-d][1,2,3]thiadiazole-6-carboxylates as potential plant activators and inducers of systemic acquired resistance (SAR) is reported. A synthetic strategy based on cyclization of the thiadiazole ring system utilizing thionyl chloride via the Hurd-Mori protocol as key step was developed. Success of the ring closure reaction turned out to be highly dependent on the nature of the N-protecting group of the pyrrolidine precursor. While electron donors such as alkyl gave only poor conversion to the required 1,2,3-thiadiazoles, an electron withdrawing substituent such as methyl carbamate gave superior yields. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Article
Synthesis and X-ray Structure of a New Pyrrolo[1,2-b]-pyridazine Derivative
Molecules 2005, 10(2), 360-366; https://doi.org/10.3390/10020360 - 28 Feb 2005
Cited by 8 | Viewed by 6277
Abstract
The synthesis, characterization and X-ray crystal structure of 2-(4-chloro-phenyl)-7-methylpyrrolo[1,2-b]pyridazine are reported. The compound crystallizes in thespace group P21/c (No.14) with a =3.8568(1), b = 11.0690(3), c = 26.4243(7) å, β =92.777(1)° and Z = 4. Accurate molecular parameters for the novel [...] Read more.
The synthesis, characterization and X-ray crystal structure of 2-(4-chloro-phenyl)-7-methylpyrrolo[1,2-b]pyridazine are reported. The compound crystallizes in thespace group P21/c (No.14) with a =3.8568(1), b = 11.0690(3), c = 26.4243(7) å, β =92.777(1)° and Z = 4. Accurate molecular parameters for the novel heterocyclic systemwere obtained from intensity data collected at 113K. The molecule assumes a planarconformation in the crystal and the packing is based on π-π stacking with interplanarspacing 3.400 å, typical of aromatic molecules with potential for displaying usefuloptical properties. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Article
The Preparation and Characterization of 5-Substituted-4-chloro-1,2,3-dithiazolium Salts and their Conversion into 4-Substituted-3-chloro-1,2,5-thiadiazoles
Molecules 2005, 10(2), 346-359; https://doi.org/10.3390/10020346 - 28 Feb 2005
Cited by 31 | Viewed by 6314
Abstract
A series of monosubstituted acetonitriles were treated with disulfur dichloride atroom temperature in CH2Cl2 to afford 5-substituted-4-chloro-1,2,3-dithiazolium chlorides 1.Where the 5-substituent was not a good leaving group the chloride salts were converted intothe corresponding perchlorate salts 2 which were sufficiently [...] Read more.
A series of monosubstituted acetonitriles were treated with disulfur dichloride atroom temperature in CH2Cl2 to afford 5-substituted-4-chloro-1,2,3-dithiazolium chlorides 1.Where the 5-substituent was not a good leaving group the chloride salts were converted intothe corresponding perchlorate salts 2 which were sufficiently stable and soluble to provideboth 1H- and 13C-NMR and cyclic voltammetry data. Several of the dithiazolium chlorideswere converted into their corresponding 4-substituted-3-chloro-1,2,5-thiadiazoles 13 ontreatment with aqueous ammonia. Mechanisms for all reactions are proposed. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Article
Valence Topological Charge-Transfer Indices for Reflecting Polarity: Correction for Heteromolecules
Molecules 2005, 10(2), 334-345; https://doi.org/10.3390/10020334 - 28 Feb 2005
Cited by 5 | Viewed by 5770
Abstract
Valence topological charge-transfer (CT) indices are applied to the calculationof dipole moments μ. The μ calculated by algebraic and vector semisums of the CTindices are defined. The model is generalized for molecules with heteroatoms andcorrected for sp3-heteromolecules. The ability of the [...] Read more.
Valence topological charge-transfer (CT) indices are applied to the calculationof dipole moments μ. The μ calculated by algebraic and vector semisums of the CTindices are defined. The model is generalized for molecules with heteroatoms andcorrected for sp3-heteromolecules. The ability of the indices for the description of themolecular charge distribution is established by comparing them with μ of the valence-isoelectronic series of cyclopentadiene, benzene and styrene. Two CT indices, μvec(vector semisum of vertex-pair μ) and μvecV (valence μvec) are proposed. The μvecVbehaviour is intermediate between μvec and μexperiment. The correction is produced in thecorrect direction. The best results are obtained for the greatest group. Inclusion of theheteroatom in the π-electron system is beneficial for the description of μ, owing to eitherthe role of additional p and/or d orbitals provided by the heteroatom or the role of stericfactors in the π-electron conjugation. The steric effect is almost constant along the seriesand the dominating effect is electronic. Inclusion of the heteroatom enhances μ, whichcan improve the solubility of the molecule. For heteroatoms in the same group, the ringsize and the degree of ring flattering are inversely proportional to their electronegativity. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Article
New Route to 3-Alkylthiazolo[3,2-a]benzimidazole Derivatives
Molecules 2005, 10(2), 327-333; https://doi.org/10.3390/10020327 - 28 Feb 2005
Cited by 12 | Viewed by 7695
Abstract
3-Alkyl-thiazolo[3,2-a]benzimidazole derivatives are obtained in high yieldsvia the corresponding 4-alkyl-N-3-(2-aminophenyl)-thiazoline-2-thiones which are easilyprepared from 1,2-diaminobenzene, CS2 and halogenoketones. This new route comparesadvantageously with the classical mercaptobenzimidazole routes in term of simplicity,isolated yields and availability of the starting materials. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Article
1,3-Dipolar Cycloaddition Reactions of 1-(4-Phenylphenacyl)-1,10-phenanthrolinium N-Ylide with Activated Alkynes and Alkenes
Molecules 2005, 10(2), 321-326; https://doi.org/10.3390/10020321 - 28 Feb 2005
Cited by 23 | Viewed by 6447
Abstract
The 3 2 cycloaddition reaction of 1-(4-phenylphenacyl)-1,10-phenanthrolinium ylide with activated alkynes gave pyrrolo[1,2- 4a][1,10]phenanthrolines 6a-d. The "one pot" synthesis of 6a,b,d from 4, activatedalkenes, Et3N and tetrakis-pyridine cobalt (II) dichromate (TPCD) is described. Thehelical chirality of pyrrolophenanthrolines 6b-d was put in [...] Read more.
The 3 2 cycloaddition reaction of 1-(4-phenylphenacyl)-1,10-phenanthrolinium ylide with activated alkynes gave pyrrolo[1,2- 4a][1,10]phenanthrolines 6a-d. The "one pot" synthesis of 6a,b,d from 4, activatedalkenes, Et3N and tetrakis-pyridine cobalt (II) dichromate (TPCD) is described. Thehelical chirality of pyrrolophenanthrolines 6b-d was put in evidence by NMRspectroscopy. Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Editorial
Sulfur-Nitrogen Heterocycles
Molecules 2005, 10(2), 318-320; https://doi.org/10.3390/10020318 - 28 Feb 2005
Cited by 74 | Viewed by 5098
Abstract
For more than a century, heterocycles have constituted one the largest areas of research in organic chemistry.[...] Full article
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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