Abstract Long-chain alka-2,3-dienoates were synthesized via the Wittig reaction from the corresponding fatty acids, and the subsequent triphenylphosphine-catalyzed [3+2]-cycloaddition to fullerene C60 afforded new lipophilic cyclopentafullerenes.

Abstract Ethyl 1,2,4-trioxo-2,4-dihydro-1H-pyrrolo[2,1-c][1,4]benzoxazine-3-carboxylates reacted with ethyl (2Z)-[2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]acetates to give ethyl 3a-[2-ethoxy-2-oxo-1-(2-oxo-2H-1,4-benzoxazin-3-yl)ethyl]-2-hydroxy-1,4-dioxo-3a,4-dihydro-1H-pyrrolo[2,1-c][1,4]benzoxazine-3-carboxylates. The product structure was confirmed by X-ray analysis.

Abstract An efficient acid-catalyzed condensation between substituted benzohydrazides and 2,3,5,6-tetrafluoroterephthalic acid to form 1,4-bis(5-aryl-1,3,4-oxadiazol-2-yl)-2,3,5,6-tetrafluorobenzenes is reported. The products were isolated in 74–87% yield and were characterized by 1H NMR, IR, and mass spectra.

Abstract The reaction of 4-acyl-2-amino-6-chloropyridine-3,5-dicarbonitriles with aromatic thiols in 1,4-dioxane in the presence of triethylamine led to the formation of 4-acyl-2-amino-6-(arylsulfanyl)pyridine-3,5-dicarbonitriles.

Abstract Diaryl sulfides have been synthesized in moderate to excellent yield by S-arylation of arenethiols with arylboronic acids using copper slag as a catalyst. Copper slag is a by-product obtained from smelting and refining of copper. Conventional heating method has been compared with the microwave-assisted technique. The proposed microwave-assisted synthesis provides excellent yields of diaryl

Abstract 1,6-Diarylhexane-1,3,4,6-tetraones reacted with 2-aminophenol and acetone according to previously unknown pathway leading to the formation of 3-aryl-3-hydroxy-1-{5-[(2-hydroxyphenyl)amino][1,1′-biphenyl]-3-yl}prop-2-en-1-ones. Similar three-component reactions with benzylamine or 2-methoxyaniline afforded mainly 2-(4-aroyl-3-hydroxy-5,5-dimethyl-1,5-dihydro-2H-pyrrol-2-ylidene)-1-arylethan-1-ones

Abstract A one-pot synthesis of papaverine hydrochloride with 99.6% purity was performed using xylene as solvent for the entire process. The critical parameters of each step, as well as the impurities generated, were identified. The overall yield was improved to 63%. The proposed synthetic procedure is suitable for industrial production.

Abstract Base-catalyzed reaction of 3-aroyl-6-halopyridine-3,5-dicarbonitriles with alcohols involved successive regioselective pyrrole ring fusion at the pyridine [c] side and nucleophilic substitution of chlorine. Pyrrole ring closure is the result of initial formation of furan ring with participation of the carbonyl and cyano groups, followed by iminolactone–lactam rearrangement. The reaction in

Abstract Yamaguchi esterification of (2Z,5S,6E)-5-(hydroxymethyl)-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienal with (2R,5R,6S,7S)-2-(methoxymethoxy)-3,3,5,7-tetramethyl-4-oxo-9-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl-6-[(triethylsilyl)oxy]nonanoic acid afforded the expected acyclic ester. Acid- and base-catalyzed Z,E-isomerization in the 2-methyl enal fragment of acyclic precursors was revealed

Abstract Three-component condensation of ethyl 1-R-2-phenyl-4,5-dihydro-4,5-dioxo-1H-pyrrole-3-carboxylates, malononitrile, and acyclic enols (acetylacetone, alkyl acetoacetates, and ethyl benzoylacetate) afforded substituted ethyl 9-amino-10-cyano-1-oxo-3-phenyl-8-oxa-2-azaspiro[4.5]deca-3,6,9-triene-4-carboxylates. The products are interesting from the viewpoint of medicinal chemistry.

Abstract 3-(2-Methylprop-2-en-1-yl)-2-sulfanylidene-7-(trifluoromethyl)-2,3-dihydroquinazolin-4(1H)-one reacted with halogens (bromine and iodine), chalcogen tetrahalides, and p-methoxyphenyltellurium trichloride in a regioselective manner to give linearly fused 2-halomethyl-2-methyl-5-oxo-8-(trifluoromethyl)-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolinium trihalides, 2-methyl-5-oxo-2-[(trihalo-λ

Abstract Chiral oxazoline ligands containing an aromatic ring were prepared from norephedrine and pyrrole-2-carbonitrile or 2-hydroxybenzoyl chloride. The synthesized ligands were used in the copper-catalyzed asymmetric addition of diethylzinc to aromatic aldehydes to provide optically active 1-arylpropan-1-ols with high conversion (92%) and enantioselectivity (up to 99% ee).

Abstract A new method has been proposed for the synthesis of pyranopyrimidinone and xanthene derivatives using zinc oxide–starch nanocomposite as catalyst under microwave irradiation. The ZnO–starch nanocomposite was characterized by X-ray diffraction and scanning electron microscopy data, and the size of the ZnO-starch nanocomposite particles was estimated at 70–90 nm. The catalyst was used in the

Abstract 2,5-Disubstituted 1,4-bis(4,5-diphenyl-1H-imidazol-2-yl)benzenes have been synthesized, and their electrochemical properties have been studied by cyclic voltammetry, in particular the effect of substituents on the redox characteristics has been examined. The reversible electrochemical redox transformation quinone–biradical of the title compounds occurs at positive potentials.

Abstract An economically and environmentally sustainable protocol has been proposed for the synthesis of N-[4-(1H-benzazole-2-yl)phenyl]phthalimides via stepwise and tandem reactions of phthalic anhydride, 4-aminobenzaldehyde, and o-phenylenediamine, N-methyl-o-phenylenediamine, 2-aminobenzenethiol, or 2-aminophenol in PEG-600 for 2–3 h in the presence of boric acid as catalyst. Binding of the synthesized

Abstract Some tert-butylcalix[4]arene derivatives were synthesized by thermal and microwave methods. The microwave method was conducted in two ways: (1) all the reactants were added in one batch and (2) the reactants were added in two batches under different conditions. Tetrabutylammonium iodide (TBAI) was used in both methods, and its effect on the reaction rate was studied. In general, the duration

Abstract A preparative procedure was developed for the synthesis of 4-[5-(1-R-1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acids which were converted to acid chlorides, and the latter reacted with aromatic and heterocyclic amines to afford a series of previously unknown 4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides. The synthesized

Abstract Methyl N-alkyl-, N-cycloalkyl-, and N-arylcarbamates were synthesized by reaction of the corresponding amines with dimethyl carbonate in the presence of binder-free FeHY zeolite. The optimal conditions (reactant ratio, amount of the catalyst, temperature, reaction time) were found to afford the target products with high yields.

Abstract Successive reactions of pentafluoronitrobenzene with resorcinol, orcinol, and tetrafluororesorcinol in acetonitrile in the presence of triethylamine afforded polyfluorinated ABAB and ABAC tetraoxacalix[4]arenes. Analysis of the1H and 19F NMR spectra of the synthesized oxacalixarenes indicated high conformational mobility of the resorcinol and tetrafluororesorcinol fragments of their molecules

Abstract The condensation of salicylaldehyde with CH acids [p-methoxyacetoacetanilide, ethyl 3-amino-3-sulfanylidenepropanoate, 3-amino-N-aryl-3-sulfanylidenepropanamides, and ethyl 2-(1,3-thiazol-2- and -4-yl)acetates] afforded 3-substituted chromen-2-ones. Some properties of the products were studied. The structures of 3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-2H-chromen-2-one, 2-oxo-2H-chromene-3-carboxamide

AbstractReaction of 2,2′,2″-(2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)triacetic acid derivatives with nucleophiles in aqueous medium involved opening of the triazinane ring with elimination of carbonyl group, followed by recyclization to 1-carbamoylhydantoins.

Abstract[2,3,7,8,12,13,17,18-Octabromo-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) and [2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) were synthesized by halogenation of [5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]zinc(II) with N-bromosuccinimide and N-chlorosuccinimide, respectively, in a mixture of chloroform with methanol. Treatment

AbstractA series of novel 5-(1,2,3-triazolylmethylsulfanyl)tetrazole derivatives were synthesized by the click reaction from 1-phenyl-5-(prop-2-yn-1-ylsulfanyl)-1H-tetrazole and the corresponding azide. The reaction optimization results showed that higher yields are obtained using CuSO4 and sodium ascorbate in DMF–water (2:1). The product structures were established on the basis of various spectral

AbstractThe synthesis of diastereoisomers via diastereoselective hydrogenation of unreactive endocyclic enamine system of ethyl 4-hydrazinyl- and 4-(2-hydroxyethylamino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylates using palladium-based catalyst was developed. The steric and electronic properties of substituents, especially of the C2 substituent, influenced both the yield and diastereoselectivity. Despite

Abstract1-Alkoxy-4-amino-3,6-dioxo-1-phenyl-2,3,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles have been synthesized with high yields by reaction of 4-amino-1-hydroxy-3,6-dioxo-1-phenyl-2,3,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitrile with the corresponding alcohols in the presence of p-toluenesulfonic acid.

AbstractThe reaction of N-(4,4-diethoxybutyl)phosphamides with chloro(diphenyl)phosphine in chloroform in the presence of acetic acid gave previously unknown 2-(diphenylphosphoryl)pyrrolidines, and hydrolysis of the latter afforded 2-(diphenylphosphoryl)pyrrolidine.

AbstractAn efficient procedure has been developed for the synthesis of analogs of the alkaloid norhygrine by reaction of 3-(arylmethylidene)-1-pyrrolines with acetone. The synthesized compounds have been converted to hydrazones by treatment with the corresponding substituted arylhydrazines.

AbstractThree-component condensations of ethyl acetoacetate with 1,3-thiazol-2-amine and aromatic aldehydes in isopropyl alcohol at 20°C under ultrasonic activation lead to the formation of ethyl 5-aryl-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylates, ethyl 5-aryl-7-hydroxy-7-methyl-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylates, or ethyl 2-hydroxy-2-methyl-2H-chromene-3-carboxylate

AbstractThe reaction of 1,3-dehydroadamantane with alkylbenzenes was studied for the first time. It involved the C–H bond of the alkyl substituent in the α-position with respect to the aromatic ring. The proposed radical mechanism of the reaction was confirmed by the isolation of 1,1′-biadamantane and 1,2-diphenylethane derivatives. Difficultly accessible (adamantan-1-ylmethyl)arenes were synthesized

Abstract2-Aminocyclododecan-1-ol and 6(3)-aminodecahydro-1,4-ethanonaphthalen-5(2)-ols (mixture of isomers) were synthesized in two steps via oxidative hydroxybromination of cyclododecene and 1,2,3,4,4a,5,6,8a(1,4,4a,5,6,7,8,8a)-octahydro-1,4-ethanonaphthalines with the system hydrogen peroxide–HBr. In the first step, oxidation of hydrogen bromide with hydrogen peroxide generated intermediate dioxidanium

AbstractA convenient synthetic route to 4-arylpyridine-2,6-dicarboxylic acid has been proposed on the basis of substituted benzaldehydes according to the Kröhnke method, followed by oxidation of methyl group.

AbstractAn asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. Based on the asymmetric methylation of chiral (S)-4-benzyloxazolidin-2-one, the carbon chain of the target molecule was assembled through a C1+C10+C4+C3 procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid and then, with the induction of Evan’s template, a

Abstract2-Acyl-4,5,6-trialkyl-3-aminothieno[2,3-b]pyridines, 8′-ethyl-7′,9′-dimethyl-1′H-spiro[cyclohexane-1,2′-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin]-4′(3′H)-one, and 7,8,9-trimethylpyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4-amine have been synthesized by one-pot three-component condensation of 3-methyl(ethyl)pentane-2,4-diones with cyanothioacetamide and α-halocarbonyl compounds, cyclohexanone,

AbstractCommercially available p-aminobenzoic acid was used as a precursor for the synthesis of novel fused, non-fused, and spiro polyheterocyclic derivatives bearing indene, imidazole, pyrazole, and/or triazine nucleus via addition to simple and accessible reagents such as ninhydrin, o-phenylenediamine, and carbon disulfide. The experimental procedures were straightforward and simple, the products

AbstractA series of N-(4-oxoadamantan-1-yl)-N′-[fluoro(chloro)phenyl]ureas have been synthesized in 27–73% yields by reaction of 1-isocyanatoadamantan-4-one with fluoro- and chlorosubstituted anilines. The products are promising as human soluble epoxide hydrolase inhibitors.

AbstractThe kinetics of the reaction of L-tyrosyl-L-proline (Tyr–Pro) with di- and trinitrophenyl benzoates in aqueous 1,4-dioxane (40 wt % of water) were studied in the temperature range 298–313 K. The reaction rate constant k298 was found to vary in the range from 0.035 to 0.564 L·mol–1·s–1, and the activation barrier changed from 39 to 51 kJ/mol. The neutral and anionic forms of the dipeptide were

Abstract2-Bromoethanesulfonyl bromide reacts with tricyclo[4.1.0.02,7]heptane and 1-methyltricyclo[4.1.0.02,7]heptane according to a radical mechanism to give products of both anti and syn addition across the C1–C7 central bicyclobutane bond having a norpinane (bicyclo[3.1.1]heptane) structure. Treatment of the adducts with triethylamine leads to the formation of vinyl sulfones as a result of 1,2-dehydrobromination

AbstractA general procedure has been developed for the rapid synthesis of 8-aryl-7H-acenaphtho[1,2-d]imidazoles in high yields using Fe3O4 NPs@GO@C4H8SO3H as a green and recyclable magnetic nanocatalyst under reflux conditions. The nanocatalyst was prepared and characterized by FT-IR, XRD, and EDX data. A variety of aromatic aldehydes underwent condensation with NH4OAc and acenaphthenequinone to give

AbstractReformatsky reagent prepared from methyl 1-bromocyclohexanecarboxylate reacted with N,N′-(1,4-phenylene)bis(1-arylmethanimines) to produce 2,2′-(1,4-phenylene)bis[3-aryl-2-azaspiro[3.5]nonan-1-ones] as a result of successive nucleophilic additions to the C=N double bonds of the substrate and intramolecular cyclization of the corresponding intermediates. The stepwise reaction mechanism was proved

AbstractDiazotization of aminopyridines in the presence of trifluoromethanesulfonic acid gives the corresponding pyridinyl trifluoromethanesulfonates instead of expected diazonium salts. Pyridinyl trifluoromethanesulfonates can be converted to N,N-dimethylaminopyridines on heating in dimethylformamide via replacement of the trifluoromethanesulfonyloxy group. The reaction is accelerated under microwave

AbstractDiastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with 3-(bromomethyl)but-3-enoate, followed by reduction with zinc, gave homoallylic alcohol which was subjected to lactonization. Opening of the lactone ring in the latter afforded methyl (3S)-5,5-dimethoxy-3-methylpentanoate with a high yield and enantioselectivity. This compound is a valuable intermediate product in

AbstractThe review systematizes published data on the use of 2-acylcycloalkanones in organic synthesis. The data are arranged in accordance with the type of products formed.

AbstractTwenty new bithiazole derivatives were synthesized by condensation of 2-{2-[(1-arylethylidene)hydrazinylidene]thiazolidin-4-ylidene}hydrazine-1-carbothioamides with halo ketones, halo esters, and α-keto hydrazonoyl halides. The structures of all prepared compounds were proposed on the basis of their IR,1H and 13C NMR, and mass spectra. All the synthesized compounds were screened for their cytotoxicity

AbstractSe-Phenyl methane-, benzene-, and 4-methylbenzenesulfonoselenoates PhSeSO2R (R = Me, Ph, 4-MeC6H4) react with 1-X-tricyclo[4.1.0.02,7]heptanes (X = Me, Ph, SiMe3) under photochemical initiation to give products of addition at the C1–C7 central bicyclobutane bond with a bicyclo[3.1.1]heptane (norpinane) skeleton, where the R-sulfonyl group is attached to C7 and is oriented syn and the phenylselanyl

AbstractThe addition of 2-bromoethanesulfonyl bromide to the central C1–C7 bond of 1-phenyltricyclo[4.1.0.02,7]heptane proceeds in a highly anti-stereoselective fashion to form 1 : 1 adducts with the norpinic structure. The action of some bases and nucleophiles on the anti-addition product was studied. It was found that, depending on the reaction conditions, the adduct undergoes solvolysis, 1,2-dehydrobromination

AbstractThe conditions of the reaction of trichloroethylene with sulfur and amines were optimized (the modified Willgerodt–Kindler reaction). The reaction of tetrachloroethylene with sulfur and some basic primary and secondary amines of the aliphatic series in DMF under mild conditions leads to N,N'-disubstituted dithiooxamides in 30–70% yields and with a 100% conversion of tetrachloroethylene.

AbstractA convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.

AbstractThe reactions of ethyl 1-aryl-4-(2-bromoacetyl)-5-methyl-1H-pyrazolocarboxylates with ortho-hydroxybenzonitrile and 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile gave previously unknown 2-aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones and 2-aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones, respectively. It was found

AbstractPreviously unknown carbofunctional organosilicon derivatives of azoles are synthesized by the reactions of sulfanyl derivatives of benzoxazole, benzothiazole, benzimidazole, and triazole with (iodomethyl)dimethyl(phenyl)silane and (iodomethyl)(ethynyl)dimethylsilane.

AbstractA simple one-pot synthesis of N-substituted benzimidazoles from aromatic carboxylic acids and aromatic 1,2-diamines in the presence of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate/hydroxybenzotriazole (HATU/HOBT) and N,N-diisopropylethylamine in DMF at 100°C, featuring good to excellent yields and easy workup, is developed. The protocol can

AbstractA novel series of 1,2,3-triazolylthiazolidinedione analogs have been synthesized by the condensation of the corresponding 1-aryl-1H-1,2,3-triazole-4-carbaldehydes with thiazolidine-2,4-dione in the presence of KOH. The title compounds were evaluated for their in vitro anticancer activity using MTT assay against four cancer cell lines: A549 (lung), HT-29 (colon), MCF-7 (breast), and A375 (melanoma)

AbstractA highly regioselective ring opening reaction of terminal epoxides with 2-bromobenzoic acid catalyzed by tetrabutylammonium bromide was accomplished. The procedure is operationally simple and practical for the synthesis of a series of β-hydroxy esters. Using this protocol, oxetan-3-ol could be prepared efficiently in a good yield.

AbstractPoly(styrene-co-maleic anhydride) (SMA) was reacted with 4-amino-6-methyl-3-thioxo-1,2,4-triazine-5-one to obtain the corresponding imide [SMI] which was used as a substrate for immobilization of PdCl2 and preparation of palladium nanoparticles (PdNPs). The supported PdNPs were fully characterized using scanning electron microscopy (SEM), energy dispersive X-ray (EDAX) and FTIR spectroscopy

AbstractAn ecofriendly, simple, and efficient one-pot protocol has been developed for the synthesis of 1,2,4,5-tetrasubstituted imidazoles by the reaction of benzil, aryl aldehydes, aliphatic or aromatic amines, and ammonium acetate, catalyzed by the acidic halogen-free ionic liquid [bmim]HSO4 under solvent-free conditions. The advantages of the proposed protocol include high yields, short reaction

AbstractChiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion

AbstractA novel series of 3,5-disubstituted-1a,3,4-oxadiazole derivatives was synthesized and screened for in vitro anticancer activity. The newly synthesized compounds were characterized by 1H, 13C NMR, IR spectroscopy and mass spectrometry. Among all the synthesized compounds, Oxaprozin derivatives containing 1,3,4-oxadiazole ring with 4-fluorobenzyl, 4-methoxybenzyl, methyl, and butyl substituents

AbstractThe enantiospecific synthesis of 3-acetoxy-trans-β-lactams via the Staudinger [2+2] cycloaddition reaction of polyaromatic imines with bicyclic (+)-car-3-ene was investigated. The sterically hindered polyaromatic substituent at the N1 position in the imines plays a significant role, directing the cycloaddition reaction to stereoselective formation of trans-(3R,4R)-N-azetidin-2-ones. The results

AbstractPotassium salts of arylmethylidene derivatives of malononitrile trimer were obtained by the reactions of aromatic aldehydes with malononitrile trimer in an aqueous medium under micellar catalysis. The optical properties of the synthesized salts were studied to show they absorb in the range of 313–436 nm, depending on the substituent. Exchange reactions with various metal salts showed that the

AbstractThe reaction of 5-(arylmethylidene)-2,4,6-pyrimidine-2,4,6(1H,3H,5H)-triones with morpholine in the presence of hydrogen peroxide and catalytic amounts of sodium tungstate leads to the synthesis of 2-aryltetrahydro-1'H,2H-spiro(isoxazole[3,2-c][1,4]oxazine-3,5'-pyrimidine)-2',4',6'(3'H)-triones.

AbstractPhenylethynyl sulfones of the general formula RSO2C≡CPh (R = p-Tol, Ph, CH3) undergo a photochemically induced anti-stereoselective addition to the central C1–C7 bond of 1-bromotricyclo[4.1.0.02,7]heptane to form monoadducts of the bicyclo[3.1.1]heptane (norpinic) series containing a syn-sulfonyl group in position 7 and a phenylethynyl moiety on C6. Treatment of the synthesized adducts with