ABSTRACT
A series of novel 1-N-α-d-glucopyranosyl-1H-1,2,3-triazole xanthines was synthesized from azido sugars (glucose, galactose, and lactose) and propargyl xanthines (theophylline and theobromine) using a typical copper (I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition. The corrosion inhibition activities of these new carbohydrate-xanthine compounds were evaluated by studying the corrosion of API 5 L X70 steel in a 1 M HCl medium. The results showed that, at 10 ppm, a 90% inhibition efficiency was reached by electrochemical impedance spectroscopy. The inhibitory efficiency of these molecules is explained by means of quantum chemical calculations of the protonated species with the solvent effect, which seems to better represent the actual situation of the experimental conditions. Some quantum chemical parameters were analyzed to characterize the inhibition performance of the tested molecules.
Subject(s)
Steel , Xanthines , Steel/chemistry , Corrosion , Triazoles/pharmacology , Triazoles/chemistry , Acids , Models, TheoreticalABSTRACT
A series of carbohydrate-linked 1,2,3-triazole derivatives were synthesized in good yields from glucofuranose and allofuranose diacetonides using as key step a three-component 1,3-dipolar azide-alkyne cycloaddition catalysed by a Cu-Al mixed oxide. In this multi-component reaction, Cu-Al mixed oxide/sodium ascorbate system serves as a highly reactive, recyclable and efficient heterogeneous catalyst for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles. The reported protocol has significant advantages over classical CuI/N,N-diisopropylethylamine (DIPEA) or CuSO4/sodium ascorbate conditions in terms of efficiency and reduced synthetic complexity. In addition, the selective deprotection of synthesized di-O-isopropylidene derivatives was also carried out leading to the corresponding mono-O-isopropylidene products in moderate yields. Some of the synthesized triazole glycoconjugates were tested for their in vitro antimicrobial activity using the disc diffusion method against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), as well as fungus (Aspergillus niger) and yeast (Candida utilis). The results revealed that these compounds exhibit moderate to good antimicrobial activity mainly against Gram-negative bacteria.
ABSTRACT
A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugiâ»three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[f][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[f][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before.
Subject(s)
Cyclization , Cycloaddition Reaction , Naphthyridines/chemical synthesis , Combinatorial Chemistry Techniques , Microwaves , Molecular Structure , Naphthyridines/chemistryABSTRACT
The pseudo-four component click synthesis of dibenzylated 1,2,3-triazoles derived from aniline is reported. The cycloaddition of sodium azide to N-(prop-2-ynyl)-benzenamine (I) in the presence of equimolar amounts of p-substituted benzyl derivatives, yields a mixture of mono- and dibenzylated 1,2,3-triazoles. When two equivalents of the benzyl derivative are added to the multicomponent reaction, the selective preparation of the dibenzylated compounds is achieved. The reactivity of the aniline N-H bond in monobenzylated 1,2,3-triazoles was tested by treatment with one equivalent of a p-substituted benzyl chloride at 40 °C, rendering the dibenzylated derivatives quantitatively.
Subject(s)
Aniline Compounds/chemistry , Triazoles/chemistry , Catalysis , Click Chemistry , Triazoles/chemical synthesisABSTRACT
New azanucleosides were obtained using sulphated zirconia (ZS) as catalyst in the nucleophilic oxirane ring opening reaction of 1-allyl-3-(oxiran-2-ylmethyl) pyrimidine-2,4(1H,3H)-dione and 1-allyl-5-methyl-3-(oxiran-2-ylmethyl)-pyrimidine-2,4(1H,3H)-dione, with (S)-prolinol. The new templates were obtained with good yields following a route which exploits the reactivity of epoxides in the presence of sulphated zirconia as catalyst. The key step was carried out using microwave and solvent-free conditions and proceeds with high selectivity.
Subject(s)
Epoxy Compounds/chemistry , Microwaves , Nucleosides/chemistry , Zirconium/chemistry , Catalysis , Molecular Structure , StereoisomerismABSTRACT
A comparison was made of the effectiveness of the functionalization reactions of pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecane-8,11-dione (PCU) using sulphated zirconia in protection-deprotection reactions and Mg/Al hydrotalcite in a cyanosilylation reaction, under classical thermal conditions and imposing microwave radiation; improved yields and reaction times were considered.
Subject(s)
Alkanes/chemical synthesis , Aluminum Hydroxide/chemistry , Chemistry, Organic/methods , Magnesium Hydroxide/chemistry , Zirconium/chemistry , Catalysis , Cyanates/chemistry , Microwaves , Silicon/chemistry , Spectroscopy, Fourier Transform Infrared , Sulfates/chemistry , X-Ray DiffractionABSTRACT
A solvent-free approach is described for the regioselective synthesis of acylals (1,1-diacetates) in shorter reaction times and higher yields, compared to conventional methodology using solvents. In the protection reaction of the o-hydroxybenzaldehyde the formation of acetyl compounds and anhydro-dimers was observed. The deprotection reaction involves microwave (MW) exposure of diluted reactants in the presence of solid sulphated zirconia (SZ) catalyst that can be easily recovered and reused. The sulphated zirconia was recycled several times without any loss of activity.
Subject(s)
Anhydrides/chemical synthesis , Benzaldehydes/chemical synthesis , Microwaves , Zirconium/chemistry , Catalysis , Dimerization , Solvents/chemistryABSTRACT
A solvent-free approach for the regioselective synthesis of beta-amino alcohols in shorter reaction times and higher yields, compared to conventional heating is described. It involves microwave (MW) exposure of undiluted reactants in the presence of sulphated zirconia (SZ) or sulphated zirconia over MCM-41 (SZM) as catalyst. Both acid materials can be easily recovered and reused.
Subject(s)
Amino Alcohols/chemical synthesis , Microwaves , Silicon Dioxide/chemistry , Solvents/chemistry , Sulfates/chemistry , Zirconium/chemistry , Amino Alcohols/chemistry , Catalysis , Chromatography, Gas , Ethylene Oxide/chemistry , Stereoisomerism , X-Ray DiffractionABSTRACT
Sulfated zirconia and SZ/MCM-41 were used as catalysts for the synthesis of beta-aminoalcohols via epoxide aminolysis. Sulfated zirconia was prepared by sol-gel and SZ/MCM-41 was obtained by impregnation. Solid catalysts were characterized by XRD, SEM-EDS, UV-Vis, FT-IR pyridine desorption and Nitrogen physisorption. Both acid materials were useful as catalysts, even when they were recycled several times. The beta-aminoalcohols were characterized by FT-IR, (1)H- and (13)C-NMR and GC-MS.
Subject(s)
Amino Alcohols/chemical synthesis , Silicon Dioxide/chemistry , Sulfates/chemistry , Zirconium/chemistry , Amino Alcohols/chemistry , Epoxy Compounds/chemistry , Microscopy, Electron, Scanning , Molecular Structure , Solvents/chemistry , X-Ray DiffractionABSTRACT
The catalytic ability of ZrO(2)/SO(4)(2-) to promote solventless three-component condensation reactions of a diversity of aromatic aldehydes, urea or thoiurea and ethyl acetoacetate was studied. Products resulting from Hantzsch and/or Biginelli multi-component reactions are obtained in the presence of solid acid catalysts using the same reactants but different temperature conditions. The sulfated zirconia catalyst can be recovered and recycled in subsequent reactions with a gradual decrease of activity.
