Benzoyl Chloride In Presence Research Articles

Design, Synthesis of Some New N-(2-fluoro-4-morpholin-4-yl-phenyl)-Substituted-Benzamide Derivatives and Screening of Their Microbial Activities

In the present work, we are reporting efficient synthesis of a series of novel fluorinated Morpholine containing benzamide derivatives and their microbial activities. In the reaction between 2-fluoro-4-morpholinobenzenamine and different substituted benzoyl chloride in presence of toluene solvent at reflux temperature to give desired products in pure form. The compounds are characterized by spectral technique like 1H NMR, IR, mass, and elemental analysis. Yields of synthesized compounds are good to excellent as well as the synthetic process is rapid. The synthetic process was shown to have advantageous such as low cost, short reaction time, mild reaction conditions, and eco-friendly. Some of the synthesized compounds exhibit potent antifungal and antibacterial activity as compared with standard drug molecules as Gentamycin, Ampicillin, Chloramphenicol, Iprofloxacin, Norfloxacin, Nystatin, and Greseofulvin.

Синтез производных 1-фенилиндолов

The growing needs of medicine and pharmacology induce synthetic organic chemistry to constantly be in the process of modernizing existing methods of synthesis and developing new ones. Since ancient times, the high physiological activity of indole derivatives has been widely known. Indole is a heterocyclic condensed aromatic compound that is part of the molecules of a multitude of compounds with biochemical and physiological value. A large number of drugs of the indole group obtained synthetically are derivatives of arylindols. One of the most common methods of obtaining arylindoles is the use of Ulman reaction conditions. However, this technique involves the use of high temperatures and a large amount of aryl halide to obtain optimal yields. Some classical methods suggest the use of palladium compounds as a catalyst, which are highly prices and require inert conditions, which limits their uses in the syntheses and reduces the overall synthetic attraction. In order to mitigate the conditions of the Ulman reaction and increase the reaction yields, methods have been proposed for the synthesis of 1-phenylindole derivatives based on the introduction of phenyldiodide by arylating the nitrogen atom in position 1 of the 5-methoxyindole indole ring in the presence of monovalent copper chloride using phenanthroline and anthracene as ligands, followed by heteroarylation the compounds obtained quinoline and isoquinoline in the presence of benzoyl chloride and 2-bromo-3-methylbutanoyl chloride. The physical and chemical characteristics of the compounds obtained were determined. Installed using 1H NMR spectroscopy and elemental analysis of the structure of the obtained derivatives are in good agreement with the proposed structural formulas. According to a review of literature data, the obtained structures can be supposedly used to research their physiological activity.

Hydrocyanation of 2-arylmethyleneindan-1,3-diones using potassium hexacyanoferrate(II) as a nontoxic cyanating agent

AbstractThe hydrocyanation of 2-arylmethyleneindan-1,3-diones with potassium hexacyanoferrate(II) as a nontoxic cyanating agent to synthesize 2-(1,3-dioxoindan-2-yl)-2-arylacetonitriles in the presence of benzoyl chloride as a promoter and potassium carbonate as a base by a one-pot procedure is described. The use of nontoxic and inexpensive cyanide source, high yield and simple workup procedures are the advantages of this protocol.

Processing, Tensile, and Thermal Studies of Poly(Vinyl Chloride)/Epoxidized Natural Rubber/Kenaf Core Powder Composites with Benzoyl Chloride Treatment

ABSTRACTThe kenaf core powder (KCP) has been treated with benzoyl chloride (BC) in poly(vinyl chloride)(PVC)/epoxidized natural rubber (ENR)/KCP composites. The presence of BC grafted on KCP was evident by infrared analysis. PVC/ENR/KCP samples were prepared using Haake Polydrive with the temperature of 140°C and KCP loading of 5, 10, 15, and 20 phr. The processing, tensile and thermal properties of the composites were investigated. The enhancement of tensile properties showed that the treatment improved the interfacial adhesion between KCP with PVC/ENR matrix. Higher glass transition temperature and higher thermal stability after treatment with BC support the enhancement of the composites’ tensile properties.

Chemoselective C-benzoylation of phenols by using AlCl3 under solvent-free conditions

Substituted phenols were chemo-selectively reacted with benzoylchloride in presence of aluminum chloride under solvent-free condition to afford the corresponding 2'-hydroxy aryl benzophenones in excellent yields (72-96%). Naphthol benzoylation resulted in lower yields as compared to phenols. Both reactions completed in 5-10 min with quantitative yields providing excellent control over regioselectivity of products. KEY WORDS: Chemoselective C-acylation, F-C reaction, Fries rearrangement Bull. Chem. Soc. Ethiop. 2015, 29(2), 319-325DOI: http://dx.doi.org/10.4314/bcse.v29i2.14

An unexpected silver triflate-catalyzed reaction of 2-alkynylbenzaldoxime in the presence of benzoyl chloride

An unexpected silver triflate-catalyzed reaction of 2-alkynylbenzaldoxime in the presence of benzoyl chloride under mild conditions gives rise to 2-(isoquinolin-1-yl)isoquinolin-1(2H)-ones in good yields.

Synthesis Of 2-Benzamidomethyl-5-Substituted Amino-1,3,4-Thiadiazoles-2,5-Disubstituted 1,3,4-Oxadiazole and 4,5-Disubstituted 1,2,4-Triazole-3-Thiol

In this paper the synthesis of some substituted 1,3,4-oxadiazoles , 1,3,4-thiadiazoles and 1,2,4-triazoles starting from amino acid and benzoyl chloride is reported. Treatment of glycine or alanine with benzoyl chloride in presence of sodium carbonate gave keto-acid(1,2), which were converted to oxazolinone (3,4) by their reaction with acetic anhydride. Oxazolinone (3,4) were treated with hydrazine hydrate to give acid hydrazides (5,6). Acid hydrazides were converted to substituted thiosemi- carbazides (7,8) by their reaction with phenyl isothiocyanate. Substituted thiosemicarbazides (7,8) were treated with sodium hydroxide and concentrated sulphuric acid give substituted 1,2,4-triazoles (9,10), 1,3,4-thiadiazoles (11,12) respectively while treatment of (7) with mercuric oxide gave 1,3,4-oxadiazoles (13). Treatment of triazoles (9,10) with 4-hydroxybenzaldehyde gave substituted triazoles (14,15). 1-Substituted thiosemicarbazide (16) was obtained from acid hydrazide (5), cyclized with sodium hydroxide to 5-Substituted-1,2,4-triazole-3-thiol (17). The structures of the synthesized compounds were confirmed by physical and spectral means.

ChemInform Abstract: 1-Ethyl-3-methylimidazolium Halogenoaluminate Ionic Liquids as Reaction Media for the Acylative Cleavage of Ethers.

Abstract Ionic liquids derived from 1-ethyl-3-methylimidazolium iodide (emimI), and aluminium chloride have been shown to be suitable solvents for the acylative cleavage of a series of cyclic and acyclic ethers. Difunctionalised ω-iodobenzoate adducts have been isolated from the cleavage of cyclic ethers performed in Lewis acidic ionic liquids (i.e. AlCl3:emimI ratio is greater than 1:1) in the presence of benzoyl chloride.

One-pot three-component synthesis of α-aminonitriles using potassium hexacyanoferrate(II) as an eco-friendly cyanide source

An efficient and environmentally friendly method has been developed for the synthesis of α-aminonitriles via one-pot three-component condensation of carbonyl compounds, amines, and potassium hexacyanoferrate(II) in the presence of benzoyl chloride as a promoter. This protocol has the features of use of eco-friendly cyanide source, high yield, and simple work-up procedure.

Synthesis and biological screening of octasubstituted-triphenodioxazines and its sulphur analogues with some novel intermediates

Abstract Attempts have been made to prepare for the first time the octasubstituted-triphenodioxazines and triphenodithiazines heterocycles by cyclisation of 3,6-dichloro-2,5-bis(2′,4′,5′-trichloroanilino)-1,4-benzoquinone and condensation. This wasfollowed by cyclisation of substituted 2-aminobenzenethiol respectively with chloranil and bromanil in ethanolic solution of fused sodium acetate in the presence of benzoyl chloride in nitrobenzene. Their structures were confirmed on the basis of their chemical and spectral analyses. Moreover, the biological activity of these compounds was evaluated against the test organisms viz — E.coli, S. aureus, B. subtilis, M.luteus and C. albicans. These compounds synthesized from 2,4,5-trichloroaniline appeared to possess significant antimicrobial activities and an explicit correlation between structure and biological activity was also observed.

<b>Synthesis, screening and QSAR studies of 3-benzoyl-2-oxo/thioxo-1,2,3,4-tetrahydro-pyrimidine analogues as antibacterial agents</b>

The purpose of this study was to synthesize several 3-benzoyl-5-acyl-6-methyl-4-substituted-2-oxo/thioxo-1,2,3,4-tetrahydropyrimidines, evaluate them for their antibacterial activity and to establish correlation between the activity and physicochemical properties. 5-Acyl-6-methyl-4-substituted-2-oxo/thioxo-1,2,3,4-tetrahydropyrimidines ( A ) were synthesized by cyclocondensation reaction between appropriate aldehyde, acetoacetate and urea/thiourea in presence of aluminium chloride and hydrochloric acid which upon treatment with benzoyl chloride in presence of pyridine in benzene furnish the title compounds ( 1-28 ) . The structures of all title compounds have been confirmed on the basis of their analytical, IR and NMR spectral data. The title compounds have been tested for antibacterial activity against Staphylococcus aureus . The compounds were divided into training and test sets. A quantitative structure activity relationship study was made using various descriptors. Several statistical expressions were developed using stepwise multiple linear regression analysis. The best quantitative structure activity relationship model was further cross validated. The study revealed that total positive partial charge (PC+) and total polar negative Van der Waals surface area (Q_VSA_PNEG) contributes negatively where as contribution of Van der Waals surface area to molar refractivity (SMR_VSA7) contributes positively to the antibacterial activity. The compounds with improved antibacterial potential can be successfully designed with selected quantitative structure activity relationship model. KEY WORDS: 2-Oxo/thioxo-1,2,3,4-tetrahydropyrimidines, Antibacterial, QSAR Bull. Chem. Soc. Ethiop. 2008 , 22(3), 391-402.

N‐Acyl‐2‐phenyliminooxazolidines as Chemoselective Monoacylating Agents.

AbstractFor Abstract see ChemInform Abstract in Full Text.

N-Acyl-2-phenyliminooxazolidines as Chemoselective Monoacylating Agents

The selective monoacylation of amino groups in the presence of other functional groups has great practical utility. N-Acylation is sometimes carried out using acyl transfer reagents developed by devising an appropriate leaving group. Several reagents have been developed for the above purpose, however, some of the reagents available are unsatisfactory in terms of their usefulnesses and selectivities. Thus, satisfactory alternatives are required. Recently we reported on the preparation of 2-phenylamino-2-oxazoline 2 based on the cyclization of N-(2hydroxyethyl)-N'-phenylthiourea. The 2-phenylamino-2oxazoline heterocyclic system is believed to be a good leaving group for a chemoselective acylating reagent of amines. Moreover, it is generally believed that reagents containing a bulky, electron accepting leaving group satisfy this requirement. Here we report that N-acyl-2-phenyliminooxazolidine 3 may be used as a neutral reagent for the chemoselective acylation of primary amine in the presence of secondary amine or alcohol, and for the acylation of the less sterically hindered amine rather than other hindered primary amines. 2-Phenylamino-2-oxazoline was readily synthesized by reacting 1,2-aminoalcohol with phenyl isothiocyanate to give the corresponding N-(2-hydroxyethyl)-N'-methylthiourea. This process was followed by the cyclo-desulfurization of the thiourea to 2-phenylamino-2-oxazoline in good yield using p-toluenesulfonyl chloride and NaOH in a onepot reaction, as described previously. Acylation of the 2phenylamino-2-oxazoline can conceivably proceed through an attack upon acyl halide either by the exo-nitrogen (to provide N-acylated-2-phenylamino-2-oxazolines) or by the endo-nitrogen (to give N-acylated 2-phenyliminooxazolidine). Acylation of 2-phenylamino-2-oxazolines 2 with acetic anhydride or benzoyl chloride in presence of tertBuOK provided the acylated endo-nitrogen product. Column chromatography yielded 3a and 3b in good yields (70% and 77%, respectively), which are stable in air and easily handled. We then evaluated the N-acyl transfer abilities of 3a-b. The acylations of several amines, i.e., benzylamine, αmethylbenzylamine, α,α-dimethylbenzylamine, and Nmethylbenzylamine were examined at room temperature in CCl4. Results were summarized in Table 1. Reaction times depended on amine bulkiness for 3a and 3b. The steric influences of substituents on the amino group were clearly demonstrated by reactions using various amines, in particular, primary amines were more reactive than secondary amines. These observed reactivity differences were attributed to differences in the steric demands of primary and secondary amines in accordance with aminolysis of esters. The hindered primary amine, α-methylbenzylamine required more time than the less hindered primary amine. Sterically hindered α,α-dimethylbenzylamine with 3a was not acylated at room temperature after 48 h (entry 4). Thus, reaction rates were greatly affected by steric bulkiness (in the environs) of the amine starting material and by that of the acylating reagent 3. The leaving group, 2-phenylamino-2oxazoline 2a-b was almost quantitatively recovered for recycling by extracting the organic layer with acidified aqueous solution. Concentration of the organic layer provided the amide product, which was then purified by column chromatography or recrystallization. The substantial observed difference between the reaction rates of hindered and less hindered amines encouraged us to examine the chemoselective acylation of amines. Thus the competitive acylations of mixtures (1 : 1 equiv) of benzylTable 1. N-Acylation of various amines using 3a-b

1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as reaction media for the acylative cleavage of ethers

Ionic liquids derived from 1-ethyl-3-methylimidazolium iodide (emimI), and aluminium chloride have been shown to be suitable solvents for the acylative cleavage of a series of cyclic and acyclic ethers. Difunctionalised ω-iodobenzoate adducts have been isolated from the cleavage of cyclic ethers performed in Lewis acidic ionic liquids (i.e. AlCl 3:emimI ratio is greater than 1:1) in the presence of benzoyl chloride.

Gas transport properties of siloxane polyurethanes

AbstractPolyurethanes (PUs) were synthesized from toluenediisocyanates (TDIs) and a polymeric diol having polydimethylsiloxane and polyoxyethylene blocks of the ABA type, ended with OH groups. Prepolymers, prepared in toluene solution using ratios [NCO]/[OH] ≥ 2, were crosslinked with triisopropanolamine (TIPA) (ratio [OH]/[NCO] = 1.1) (two‐step process). PUs were also obtained with a one‐step process using, contemporaneously, TDI, block copolymer, and, as crosslinking agent, TIPA or the glyceride of ε‐hydroxyhexanoic acid. Polydimethylsiloxane (PDMSO) was prepared as a reference material. The course of the reaction between block copolymer and TDI was studied by differential scanning calorimetry in the absence and presence of benzoyl chloride (BzCl). Without BzCl, with ratios [NCO]/[OH] > 2, uncontrolled crosslinking side reactions occur. The properties of the PU films obtained with the two methods were studied both for the density of crosslinking and for gas transport properties. The two‐step polymers are less crosslinked than the others and are characterized by higher diffusion coefficients and by higher permeability to gases. The permeability order is 10−9 (N cm3 cm−1 cm−1 cm Hg−1 s−1) for CH4, O2, CO, and N2 and is 10 times higher for CO2. The selectivity for the couple O2/N2 is higher than that obtained with PDMSO films. Considerable selectivities are shown for the couples CO2/N2 and CO2/CO. © 1995 John Wiley & Sons, Inc.

A new fluorescent triphenodioxazine dye derived from 4-aminodiphenylamine

A new substituent triphenodioxazine compound containing the 3,10-di(N-benzoyl-N-phenyl) amino has been synthesized. The benzoyl groups were introduced into the molecule during the cyclization of the dianilide derived from 4-amino-diphenylamine in the presence of benzoyl chloride as ring closure agent. The absorption and fluorescence spectra of the dye were measured in five solvents and it was found that the fluorescence quantum yields, Stokes shifts and molar extinction coefficients varied linearly with E T of the solvents. When using p-toluene sulphonyl chloride as ring closure agent, p-toluene sulphonyl groups were also introduced.

ChemInform Abstract: 5‐Benzopyridyl‐Substituted 2‐Methyl‐ and 2‐Methyleneindolines.

AbstractQuinoline (I) or isoquinoline (V) react with the tetramethylindoline (II) in the presence of benzoyl chloride (III) to give the adducts (IV) and (VI) respectively.

5-Benzopyridyl-substituted 2-methyl- and 2-methyleneindolines

A method of synthesis of 5-(isoquinol-l-yl)- and 5-(quinol-2-yl)-1,3,3-trimethyl-2-methyleneindolines has been developed consisting of hetarylation of 1,2,3,3-tetra-methylindoline with isoquinoline and quinoline in the presence of benzoyl chloride, followed by oxidation and aromatization of N-benzoyl-1,2-dihydrobenzopyridine derivatives of 1,2,3,3-tetramethylindoline formed at the first stage to 5-benzopyridyl-substituted 2-methylene-indolines.

Naphthyridines in hetarylation reactions

The reaction of indole (2-methylindole) with 1,5-, 1,6-, and 1,8-naphthyridines at 20‡C, in the presence of benzoyl chloride, leads to the preferential formation of dihydro structures with one indolyl substituent at the α-position to the hetero atom. With increase in temperature, dibenzoyl and monobenzoyl tetrahydro-substituted naphthyridines with two indolyl residues in both pyridine rings are formed besides the above compounds.

ChemInform Abstract: STUDIES ON TERTIARY AMINE OXIDES. LXXIX. REACTIONS OF 2‐ETHOXYCARBONYL‐1‐HYDROXYINDOLE IN THE PRESENCE OF ACYLATING AGENTS

The Vilsmeier-Haack reaction of 2-ethoxycarbonyl-1-hydroxyindole (2) did not give 3-formylindoles but gave 3-chloro-2-ethoxycarbonylindole (3). The electrophilic reaction of 2 with quinoline 1-oxide (4) in the presence of benzoyl chloride or tosyl chloride also failed, 1-benzoyloxy-2-ethoxycarbonylindole (6) or 3 being formed, respectively. The reaction of 2 with tosyl chloride, benzoyl chloride or acetic anhydride gave the corresponding 3-acyloxy-2-ethoxycarbonylindoles (7, 8 and 11) in unsatisfactory yields. Treatment of 2 with tosyl chloride and 1-morpholinocyclohexene in pyridine-dimethylformamide afforded 2-ethoxycarbonyl-3-(2-oxocyclohexyl) indole (13) after hydrolysis of the reaction mixture.