Anhydrous Sodium Acetate Research Articles

Synthesis, spectral analysis and in vitro microbiological evaluation of 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones as a new class of antibacterial and antifungal agents

In the present work, a new series of bis hybrid heterocycle comprising both piperidine and thiohydantoin nuclei together namely 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones 46– 60 was synthesized by the treatment of the respective thiosemicarbazones 31– 45 with chloroethyl acetate and anhydrous sodium acetate in refluxing ethanol for 4 h and were characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR ( 1H, D 2O exchanged 1H and 13C), two dimensional HOMOCOSY and NOESY spectroscopic data. In addition, the title compounds were screened for their antimicrobial activities against a spectrum of clinically isolated microbial organisms. Compounds 47– 50, 52– 55 and 57– 60 with fluoro, chloro, methoxy or methyl functions at the para position of phenyl rings attached to C-2 and C-6 carbons of piperidine moiety along with and without methyl substituent at position C-3 of the piperidine ring exerted potent biological activities against Staphylococcus aureus, β- Hemolytic streptococcus, Vibrio cholerae, Escherichia coli, Pseudomonas aeruginosa, Aspergillus flavus, Candida albicans, Candida 6 and Candida 51 at a minimum inhibitory concentration.

Preparation and magnetic property analysis of monodisperse Co–Zn ferrite nanospheres

Abstract Monodisperse Co–Zn ferrite (Co 1− x Zn x Fe 2 O 4 ) nanospheres have been synthesized by the solvothermal method. In this process, glycol was used as a solvent, anhydrous sodium acetate was used as an alkalinity additive and polyethylene glycol 200 was used as a surfactant. The as-prepared samples were characterized in detail by X-ray diffraction (XRD), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), high-resolution transmission electron microscopy (HRTEM), selected area electron diffraction (SAED), energy-dispersive X-ray spectroscopy (EDX) and vibrating sample magnetometer (VSM). Results showed that a large number of high purity Co 1− x Zn x Fe 2 O 4 nanocrystallites were synthesized and these nanocrystallites underwent oriented aggregation to form nanospheres. The variation of saturation magnetization ( M s ) value of the samples was studied. The maximum saturation magnetization value of the as-prepared sample (Co 0.5 Zn 0.5 Fe 2 O 4 ) reached 64.6 emu g −1 .

Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazole derivatives

Novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazoles (3a-f) were synthesized from benzisoxazolyl-3-acetic acid and thiosemicarbazide. Reaction of 3 with bromine in glacial acetic acid in the presence of anhydrous sodium acetate yielded the corresponding 5-bromo derivatives (4a-f). While compound 3 furnished the 5-nitroso derivatives (5a-f) on refluxing with sodium nitrite solution. Thiocyanato derivatives (6a-f) were obtained by treating the imidazothiadiazole 3 with bromine and potassium thiocyanate in glacial acetic acid at room temperature. The structures of the newly synthesized compounds were confirmed by IR, NMR, mass and elemental analysis. All the compounds were screened for their antibacterial and antifungal activities. Some of the compounds displayed very good antibacterial and antifungal activity.

Nonisothermal crystallization kinetics of nucleated poly(ethylene terephthalate)

AbstractStudies of the nonisothermal crystallization kinetics of poly(ethylene terephthalate) nucleated with anhydrous sodium acetate were carried out. The chemical nucleating effect was investigated and confirmed with Fourier transform infrared and intrinsic viscosity measurements. The Avrami, Ozawa, and Liu models were used to describe the crystallization process. The rates of crystallization, which initially increased, decreased at higher loadings of the additive. The activation energy, calculated with Kissinger's method, was lower for nucleated samples. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009

Synthesis of new 5-alkyl substituted 4-thiazolidinones utilising condensation with ethyl 2-bromo alkanoates

2-[(3-Ethyl-4-oxo-3,4-dihydroquinazolin-2-yl)mercaptoacetylhydrazono]-3-alkyl/aralkyl-5-ethyl/propylthiazolidin-4-ones were synthesised by the cyclisation of 1-[(3-ethyl-4-oxo-3,4-dihydroquinazolin-2-yl)mercaptoacetyl]-4-alkyl/aralkyl thiosemicarbazides with ethyl 2-bromobutanoate or ethyl 2-bromopentanoate in the presence of anhydrous sodium acetate in anhydrous ethanolic medium. The regioisomer 2-alkyl/aralkyl 3-[(3-ethyl-4-oxo-3,4-dihydroquinazolin-2-yl)mercaptoacetylamino]-5-ethyl/propylthiazolidin-4-ones were not formed.

The Behaviour of Some Acylthiosemicarbazides in the Reaction with a-Halogenated Esters

New six unexpected 1,3,4-oxadiazoles were obtained starting from acylthiosemicarbazides. N1-[4-(4-X-phenylsulfonyl)benzoyl]-N4-(2/3-methoxyphenyl)-thiosemicarbazides 2,3a-c were treated with ethyl chloro- or bromoacetate in presence of anhydrous sodium acetate in order to obtain new thiazolidin-4-ones compounds. However, formation of desired thiazolidin-4-ones from these acylthiosemicarbazides failed and instead 1,3,4-oxadiazoles were obtained. For confirmation presence of these compounds, 5-[4-(phenylsulfonyl)phenyl]-2-(3-methoxyphenylamino)-1,3,4-oxadiazole 5a was synthetized by cyclodesulfurization of acylthiosemicarbazide 3a with mercury (II) acetate. The structures of these compounds were elucidated by FTIR, UV, 1H-NMR and 13C-NMR, MS spectra and elemental analysis.

Arylhydrazononitriles as Building Blocks in Heterocyclic Synthesis: Synthesis of New Benzothiazolyl-1,2,3-triazole Amines and -1,2,3-triazol-4-yl-1,3,4-thiadiazol-5-ylamines

- Benzothiazole-2-ylacetonitriles 6a-b and 5-benzoylamino-l,3,4-thiadiazol-2-ylacetonitrile 6c-d coupled with aromatic diazonium salts to yield arylhydrazones 7a-d. Compound 7a-d reacted with hydroxylamine hydrochloride in ethanolic sodium acetate to yield the corresponding amidoximes 8a-d. Compounds 8a-d cyclized readily into the 1,2,3-triazole derivatives 9a-d upon reflux in ethanolic DMF in the presence of anhydrous sodium acetate.

Synthesis and Reactions of Some Substituted Heterocyclic Systems as Anti-arrhythmic Agents

A series of substituted heterocyclic systems were prepared from N1-[4-(2-thienylmethylene)phenyl]-5-chloro-2-methoxybenzamide, which was prepared from the corresponding 5-chloroanisic acid (2-methoxy-4-chlorobenzoic acid) as starting material. Condensation of the thienylmethylene derivative with guanidine hydrochloride, urea, or thiourea afforded the aminopyrimidine, pyrimidinone, and thioxopyrimidine derivatives. The latter was condensed with chloroacetic acid to yield a thiazolopyrimidine, which was condensed with 2-thiophenealdehyde to yield the arylmethylene derivative, however, it was also prepared directly from thiopyrimidine by the action of chloroacetic acid, 2-thiophenealdehyde, and anhydrous sodium acetate. Treating of the thienylmethylene derivative with phenylhydrazine or hydrazine hydrate in dioxane afforded N-phenylpyrazoline and a pyrazoline, which was reacted with acetyl chloride in dioxane affording the N-acetyl analogue. The thienylmethylene derivative was reacted with malononitrile or ethyl cyanoacetate in the presence of ammonium acetate to yield the corresponding cyanoaminopyridine and cyanopyrimidone derivatives. Also, it was reacted with hydroxylamine hydrochloride in pyridine to give the oxime derivative, which was cyclized with acetic anhydride. On the other hand, condensation of the thienylmethylene derivative with ethyl cyanoacetate in the presence of sodium ethoxide or cyanothioacetamide gave the cyanopyrane and pyridine thione derivative, which was treated with ethyl chloroacetate affording the ethyl carboxylate derivative. The pharmacological screening showed that many of these compounds have good anti-arrhythmic activity and low toxicity.

One pot solvent-free synthesis of 2H-pyrano, 2H-thiopyrano, 2H-selenopyrano[2,3-b]-1,8-naphthyridin-2-ones on solid phase catalyst under microwave irradiation

A simple and efficient procedure has been developed for the synthesis of the 2H-pyrano (3a–c), 2H-thiopyrano (5a–c), 2H-selenopyrano[2,3-b]-1,8-naphthyridin-2-ones (7a–c) by cyclisation of 2-chloro-3-formyl[1,8]naphthyridines (1a–c) with acetic anhydride under microwave irradiation using solid phase catalyst anhydrous sodium acetate. These new compounds were characterized by elemental analysis, IR, 1H NMR and mass spectral studies.

Synthesis, Reactions, and Anti-arrhythmic activity of Substituted Heterocyclic Systems Using 5-Chloroanisic Acid as Starting Material

A series of substituted heterocyclic systems were prepared from N1-[4-(4-fluorocinnamoyl)phenyl]-5-chloro-2-methoxybenzamide, which was prepared from the corresponding 5-chloroanisic acid (2-methoxy-4-chlorobenzoic acid) as starting material. Treating of the cinnamoyl derivative with hydrazine hydrate in dioxane afforded a pyrazoline, which was reacted with morpholine and paraformaldehyde to give the N-substituted pyrazoline. Acylation of pyrazoline with acetyl chloride in dioxane afforded the N-acetyl analogue. Also, the cinamoyl derivative was reacted with methylhydrazine, phenylhydrazine, or ethyl cyanoacetate to yield the corresponding N-methyl-, N-phenylpyrazoline, pyrane, and pyridone derivatives. Condensation of the cinnamoyl derivative with cyanothioacetamide gave the pyridinethione derivative, which was treated with ethyl chloroacetate affording the ethyl carboxylate derivative. Also, it was reacted with malononitrile or ethyl acetoacetae to give the cyano amino analougues and ethyl carboxylate, which was reacted with methylhydrazine to give the (indazolyl)phenyl derivative. On the other hand, reaction of cinnamoyl derivative with acetyl acetone afforded the cyclohexenyl derivative, which was reacted with hydrazine hydrate to give the [methylindazolyl]phenyl derivative. Condensation of the cinnamoyl derivative with guanidine hydrochloride or thiourea afforded the aminopyrimidine derivative and thioxopyrimidine. The latter was condensed with chloroacetic acid to yield a thiazolopyrimidine, which was condensed with 2-thiophenealdehyde to yield the arylmethylene derivative, however, it was also prepared directly from thiopyrimidine by the action of chloroacetic acid, 2-thiophenealdehyde, and anhydrous sodium acetate. The pharmacological screening showed that many of these compounds have good anti-arrhythmic activity and low toxicity.

Synthesis and Antimicrobial Evaluation of Some New Thiadiazinotriazinones Carrying 4-Methylthiobenzyl Moiety

A series of 8 H-7-(substituted aryl)-3-(4-methylthiobenzyl)-1,3,4-thiadiazino[2,3- c]-1,2,4-triazin-4-ones ( 4 ) were synthesized in good yield by condensing 4-amino-6-(4-methylthiobenzyl)-3-mercapto-1,2,4-triazin-5(4 H)-one 1 with various substituted phenacyl bromides (2) in presence of anhydrous sodium acetate, followed by the cyclization of the intermediate triazinone derivatives (3) in presence of concentrated sulphuric acid. The structures of the newly synthesized compounds were formulated on the basis of elemental analysis, IR, 1H NMR and mass spectral studies. The newly synthesized compounds were tested for their in vitro antibacterial and antifungal activity against a variety of microorganisms.

Studies with enamines: Reactivity of N,N‐dimethyl‐N‐[(E)‐2‐(4‐nitrophenyl)‐1‐ethenyl]amine towards nitrilimine and aromatic diazonium salts

Abstractmagnified imageIn the presence of triethylamine, cycloaddition reaction of enamine 1 with hydrazonoyl halides 2 followed by dimethylamine elimination was achieved, yielding the corresponding 1,3,4‐trisubstituted pyrazoles 4. Coupling of enamine 1 with aromatic diazonium salts afforded 2‐(arylhydrazono)‐2‐(4‐nitrophenyl)acetaldehyde 9 in good yield. Refluxing the phenyl hydrazone 9a with chloroacetone in ethanol in the presence of triethylamine afforded 1,3,5‐trisubstituted pyrazole 12a, formed via intermediate 11a. Reaction of 9a with hydroxylamine hydrochloride in ethanol in the presence of anhydrous sodium acetate yielded oxime 13a which was irradiated in a microwave oven in the presence of acetic acid to afford a mixture of 15a and 16a.

Synthesis, Partition Coefficient and Antibacterial Activity of 3′‐Aryl‐6′‐phenyl(substituted)‐cis‐5′a,6′‐dihydrospiro [3H‐indole‐3,4′‐thiozolo(5′,1′‐c)‐isoxazolo‐2‐(1H)‐ones

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Utility of Cyanoacetamides as Precursors to Pyrazolo[3,4-d]pyrimidin-4-ones, 2-Aryl-6-substituted 1,2,3 Triazolo[4,5-d]pyrimidines and Pyrazolo[1,5-a]pyrimidine-3-carboxamides

Cyanoacetamides (7a-c) were prepared via reacting cyanoacetic acid (5) with amines in the presence of acetic anhydride. Compounds (7a-c) coupled with benzenediazonium chloride to yield the phenylhydrazones (8a-c). These reacted with chloroacetonitrile to yield aminopyrazolecarboxamides (lla-c). Reaction of (8a,b) with hydroxylamine hydrochloride in DMF in presence of anhydrous sodium acetate afforded the amino-l,2,3-triazolecarboxamides (36a,b). Also compounds (7a-c) reacted with dimethylformamide dimethylacetal (DMFDMA) to yield the enamines (9a-c) which react with hydrazine hydrate to afford the aminopyrazoles (16a-c). Compounds (16) and (36) reacted with DMFDMA to yield the title heterocyclic derivatives.

Synthesis of 1,3,4‐Oxadiazole Acyclo C‐Nucleosides Bearing 5‐Methylthio{7‐substituted‐1,2,4‐triazolo[1,5‐d]tetrazol‐6‐yl}moieties

AbstractOxidative cyclization of the sugar hydrazones (3a‐f) derived from {7H‐1,2,4‐triazolo[1,5‐d]tetrazol‐6‐ylsulfanyl}acetic acid hydrazide (1) and aldopentoses 2a‐c or aldohexoses 2d‐f with bromine in acetic acid in the presence of anhydrous sodium acetate, followed by acetylation with acetic anhydride gave the corresponding 2‐(per‐O‐acetyl‐alditol‐l‐yl)‐5‐methylthio{7H‐1,2,4‐triazolo[1,5‐d]tetrazol‐6‐yl}‐1,3,4‐oxadiazoles (5a‐f). Condensative cyclization of the sugar hydrazones (3a‐f) by heating with acetic anhydride gave the corresponding 3‐acetyl‐2‐(per‐O‐acetyl‐alditol‐1‐yl)‐2,3‐dihydro‐5‐methylthio{7‐acetyl‐1,2,4‐triazolo[1,5‐d]tetrazol‐6‐yl}‐1,3,4‐oxadiazoles (11a‐f). De‐O‐acetylation of the acyclo C‐nucleoside peracetates (5 and 11) with methanolic ammonia afforded the hydrazono lactones (7) and the acyclo C‐nucleosides (12), respectively. The structures of new oxadiazole derivatives were confirmed by analytical and spectral data.

Facile synthesis of non-steroidal anti-inflammatory active bisbenzamide-containing compounds

A variety of N, N′-bis{2-[1,2-ethanediylbis(oxy-2,1-phenylene)]-1-(substituted carbonyl)ethenyl}benzamides 7a– c, 9a– d were synthesized via nucleophilic attack of either primary 8 or secondary amines 6 on bisoxazol-5(4 H)-one 5. The latter was obtained through the reaction of 2,2′-[1,2-ethanediylbis(oxy)]bisbenzaldehyde ( 4) with hippuric acid in acetic anhydride in the presence of anhydrous sodium acetate. The anti-inflammatory properties of the prepared compounds were screened using carrageenan-induced paw oedema in rats. Many of the prepared bisbenzamide-containing compounds show considerable in vivo anti-inflammatory activity, especially 7b which reveals remarkable pharmacological properties comparable with ketoprofen (which was used as a reference standard) at successive time intervals (1, 2, 3, 4 and 24 h).

Reactions of 4-chloro-3-formyl-coumarin with primary amines

The reaction of 4-chloro-3-formylcoumarin with primary amines in the presence of triethylamine was studied. The reaction with aliphatic and aromatic amines leads to N-substituted 4-amino-3-formylcoumarins, whereas hetarylamines react primarily with the formyl group to form a mixture of the Z-and E-isomers of N-substituted 3-aminomethylenechroman-2,4-diones. Replacement of the triethylamine by anhydrous sodium acetate in the reaction of chlorocoumarin with 2-aminopyridines leads to the formation of the condensed benzopyranopyridopyrimidine system as a result of nucleophilic attack of the amino group by the chlorine atom at position 4.

Synthesis of Alkoxyphthalimide Derivatives of 5‐Arylidene‐2‐(6′‐chlorobenzothiazol‐2′‐yl‐imino)‐4‐thiazolidinones.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Synthesis and antibacterial activity of 2-(2,4-dinitrophenyl)-3,5-diphenyl (substituted)-6-aryl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d] thiazoles

A series of Schiff's bases have been prepared by condensation of substituted benzaldehydes with primary arylamines and the corresponding 4-thiazolidinones have been prepared by the reaction of Schiff's bases with thioglycolic acid in benzene. The resulting 4-thiazolidinones on reaction with substituted benzaldehydes in anhydrous sodium acetate by Knoevenagel's condensation have afforded 2-phenyl(substituted)-3-aryl-5-benzilidine(substituted) thiazolidine-4-ones, which on cyclization with phenyl hydrazine in anhydrous sodium acetate have furnished the title compounds. The structures have been established on the basis of spectral data. All the compounds have been screened in vitro for their antibacterial activity. The results of antibacterial activity study revealed promising inhibitory activity for 3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d] thiazole derivatives with 4-chloro and 4-nitro phenyl substitutions at 5-position against all the tested strains.

Synthesis, Partition coefficient and antibacterial activity of 3' -aryl-6' -phenyl(substituted)-cis-5' α,6' -dihydrospiro[3H -indole- 3,4' -thiozolo( 5' ,1' -c )-isoxazolo-2-(1H)-ones

Condensation of isatin with primary aryl amines gave a series of Schiff bases (1) which on reaction with thioglycolic acid in 1,4-dioxane afforded the corresponding thiazolidones (2). Compound 2 on condensation with substituted benzaldehydes in anhydrous sodium acetate furnished 3-aryl-5'-phenyl(substituted)spiro[3H-indole-3,2'-thiazolidines]-2-(1H), 4'(5'H))-diones (3). The latter on reaction with hydroxylamine hydrochloride in anhydrous sodium acetate gave the title compounds (4). The structures have been established on the basis of spectral data. The Partition coefficient for n-octanol/water solvent system and in vitro antibacterial activity of this compounds have been evaluated.