Abstract The reactions of 2,2-dichlorovinyl ketones with hydroxylamine hydrochloride give the corresponding oximes. The subsequent heterocyclization of the latter under the action of t-BuOK in t-BuOH results in selective formation of 5-chloro-3-alkyl- or 5-chloro-3-aryl-substituted isoxazoles in good yields.

Abstract The reactions of benzamidine, 4-methyl-, 4-iso-butoxy-, and 4-butoxybenzamidine hydrochlorides with chalcone and substituted chalcones in alcohol in the presence of KOH yielded 2,4,6-triarylpyrimidines. 4-Phenyl-2,6-bis(4-methylphenyl)pyrimidine and 1,3-bis(4-phenyl-6-{4-[(E)-styryl]phenyl]pyrimidin-2-yl}benzene) were reacted with (2-chlorophenyl)[(1E)-phenylmethylene]amine in the system KOH/LiH/DMF

Abstract The Michael adducts of levoglucosenone and cyclohexanone were used to develop a rapid synthesis of nonano-9-lactones fused to a pyran ring containing a pharmacophoric dichloromethylene substituent. The key step in the synthesis is a cleavage, under the action of pyridinium chlorochromate, of the bridge in the hexahydrochroman formed by the etherification of the keto function by the hydroxyl

Abstract The catalytic activity of C,N-chelate diaminocarbene palladium(II) complexes containing a 3,4-diaryl-1H-pyrrol-2,5-diimine fragment in a copper-free Sonogashira reaction was studied. Reactions catalyzed by C,N-chelate diaminocarbene palladium(II) complexes do not require preliminary degassing, since such catalysts are air- and moisture-stable. In this work, comparative analysis of the catalytic

Abstract A simple and efficient method for derivatization of the pyrimidine nucleus is developed. The readily available 6-amino-2-thioxo-2,3-dihydropyrimidin-4(1H)-one has been used as a versatile building block for the synthesis of thioxopyrimidine derivatives. A variety of novel fused pyrimidines has been prepared via nucleophilic and/or electrophilic reactions of thioxopyrimidine derivatives. The

Abstract The reaction of 5,7-dinitroquinolin-8-ol with NaBH4 produces a reactive hydride σ-complex, the treatment of which with a solution of acetic acid gives 5,7-dinitro-5,6-dihydroquinolin-8-ol. The protonation of the acetone σ-complex of 5,7-dinitroquinolin-8-ol forms a mixture of the tautomers 5,7-dinitro-6-(2-oxopropyl)-6,7-dihydroquinoline-8(5H)-one and 5,7-dinitro-5,6-dihydro-6-(2-oxopropyl)quinolin-8-ol

Abstract The first stereoselective total synthesis of the linear pentaketide Modiolin has been performed via Jacobsen’ hydrolytic kinetic resolution and 2C-Wittig homologation as key steps.

Abstract Methyl (E)-3-[(4S,5S)-5-acetyl-2,2-dimethyl-1,3-dioxolan-4-yl)]prop-2-enoate obtained from D-ribose eliminates water on storage and transforms into a bicyclic crystalline “dimer”.

Abstract The reaction of 3-aryl-1-(2-hydroxyphenyl)prop-2-en-1-ones with methyl 1-bromocyclohexanecarboxylate and zinc resulted in the isolation, after hydrolysis of the reaction mixture, of spirodihydropyran-2-ones containing a 1-(2-hydrohybenzoyl)cyclohexyl substituent in the 6-position. The structure of the products was confirmed X-ray diffraction analysis.

Abstract A one-pot synthesis of 3-amino-2-aryl-1,2,5,6,7,8-hexahydroisoquinolin-1-ones by the nucleophilic substitution at position 1 of the pyridine ring was developed. The synthesized compounds were used to prepare 1-amino-7,8,9,10-tetrahydropyrimido[4,5-c]isoquinoline derivatives. The biological properties of the products were studied.

Abstract An efficient and simple continuous-flow synthetic protocol for novel quinoline-tethered pyrazoline derivatives, which involves condensation of 2-chloroquinoline-3-carbaldehydewith arylmethyl ketones followed by cyclisation with phenyl hydrazine, was developed. The newly synthesized pyrazolines were characterized by IR, 1H and 13C NMR spectroscopy, mass spectrometry, and elemental analysis

Abstract A number of chiral chelating conjugates combining a bispidine central backbone and one or two pinene side fragments were synthesized. It was shown for the first time that the synthesized compounds are capable to act as catalysts in the Henry reaction both individually and in the presence of metal salts. It was found that the best catalytic results were shown for bis-tertiary amine combining

Abstract A new series of chalcones bearing two or more 3,4-ethylenedioxythiophene fragments were synthesized, and their optical properties were studied. The Stokes shifts (Δλ) and band gaps (Egopt) were calculated on the basis of the absorption and emission spectra. The largest Stokes shift (115 nm) was found for a symmetrical product of the terephthalaldehyde and 3,4-ethylenedioxythiophene-2-carbaldehyde

Abstract The review presents analysis of the literature on the intramolecular cyclization of N-(2-acylaryl)amides, known as the Camps reaction, as well as close analogs of these compounds, N-(3-oxoalkenyl)- and N-(3-oxoalkyl)amides, which contain an amide and a carbonyl groups and react by the aldol–crotonic type. The potential, limitations, and regularities of these reactions leading to quinoline-2(1H)-ones

Abstract 2-[(2-Sulfanyl-1H-benzo[d]imidazol-5-yl)iminomethyl]phenyl naphthalene-2-sulfonate was obtained as a result of the reactions of 5-amino-2-sulfanylbenzimidazole with 2-(2-naphthylsulfonyloxy)benzaldehyde. The newly synthesized compound was characterized using IR, 1H and 13C NMR spectroscopy. Theoretical investigations of the thione–thiol tautomerism of the molecule were performed using DFT/

Abstract A new synthetic approach to fused azepines was demonstrated on an example of the synthesis of 2-methyl-2,3,4,5-tetrahydro-1H-[1]benzothieno[2,3-c]azepine. The key stage of the synthesis is the formation of the azepine ring under the Eschweiler–Clark reaction conditions. The Gibbs energy of activation for the inversion of the azepine ring was determined by dynamic 1H NMR spectroscopy. Molecular

Abstract In the present paper we synthesized 10 unique pyrimidine scaffolds (Lanso Aminopyrimidines) derived from 4-(2,2,2-trifluoroethoxy)-2-(chloromethyl)-3-methylpyridine as a core molecule, which can be used for the design of more potent and effective anticancer agents. The in vitro anticancer activities of the synthesized new pyrimidine derivatives were screened at the National Cancer Institute

Abstract A series of 1,3-disubstituted ureas containing a bicyclic lipophilic group of natural origin were synthesized by the reactions of bicyclo[2.2.1]heptane-2-yl isocyanate with amines in yields of up to 82% and by the reactions of bicyclo[2.2.1]heptan-2-amine and 1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine with 1,1'-carbonyldiimidazole in yields of up to 94%. The synthesized ureas are potent inhibitors

Abstract The intermolecular cyclization of N-benzyl-2-cyanoacetamide with carbon disulfide followed by intramolecular cyclization gave thioxothiazinone 3. This compound was used to synthesize a series of novel fused furopyrrole, pyridine, pyrimidine and other azine and azole derivatives. The Michael-type reaction of compound 3 with maleic anhydride followed by pyrrole and furan cyclizations and aromatization

Abstract The reactions of aliphatic amines containing terminal acetylene groups with Finland trityl afford its mono-, bi-, and triacetylene derivatives. These derivatives are valuable reagents for targeted insertion of spin labels via the CuAAC click reaction.

Erratum

Abstract Trifluoroacetic anhydride was used as an efficient activator of the acylation of aryl methyl ketones with carboxylic acids in the presence of Brønsted and Lewis acids (SF3SO3H, MeSO3H, 4-MeC6H4SO3H·H2O, BF3·Et2O). In all cases, the products were the corresponding β-diketones. In the reactions in the presence of boron trifluoride–diethyl ether complex, the products were isolated as BF2-chelates

Abstract The alkylation of 3-hyroxycycloalka[c]- and 6-hydroxypyrano[3,4-c]pyridines with ethyl chloroacetate and ethyl 4-chlorobutanoate gave the corresponding oxy esters which were converted to amides by reaction with various amines. The synthesized acetamide derivatives underwent base-catalyzed Smiles type rearrangement to 3-aminotetrahydroquinolines or intramolecular cyclization to 1-aminofuro[2

Abstract Treatment of 2-[(4-hydroxybutyl)amino]-1H-benzimidazole with ω-bromoacetophenones gave 1-aroylmethyl-substituted derivatives which underwent cyclization to 2-aryl-1-(4-bromobutyl)imidazo[1,2-a]benzimidazole hydrobromides on heating in concentrated hydrobromic acid when Ar = Ph, 4-ClC6H4, 4-BrC6H4, and 4-O2NC6H4. The corresponding bases were readily converted into peri-fused tetrahydro[1,3]diazepino[1

Abstract The reaction of 2-imino-2,5-dihydrofuran-3-carboxamides with benzaldehyde in pentan-1-ol in the presence of piperidine gave new dihydrofuran derivatives with a fused pyrimidine ring and two phenyl rings, 2-phenyl-5-(2-phenylethylidene)-5,6-dihydrofuro[2,3-d]pyrimidin-4(3H)-ones. The product structure was confirmed by spectroscopic methods (1H and 13C NMR) and independent synthesis from previously

Abstract A new, simple, metal-free, and eco-friendly procedure has been proposed for the oxidation of alcohols with Oxone (potassium peroxymonosulfate) in water in the presence of six phase-transfer catalysts (PTC). Phase-transfer catalysts were found to display high catalytic activity in water solution. Furthermore, the oxidation of alcohols was also carried out with relatively good conversion and

Abstract Isotianil [N-(2-cyanophenyl)-3,4-dichloro-1,2-thiazole-5-carboxamide] has been synthesized in a good yield with high purity by reaction of the key intermediate product, N-(2-carbamoylphenyl)-3,4-dichloro-1,2-thiazole-5-carboxamide, with thionyl chloride in N,N-dimethylformamide at 60°C. The structure of isotianil was studied by X-ray analysis. It crystallized in triclinic space group P1 with

Abstract cis-8-Methoxy-1,3-diazaspiro[4.5]decane-2,4-dione, the key intermediate in the synthesis of spirotetramat, was synthesized by catalytic hydrogenation, oxidation, and Bucherer–Bergs reaction with 4-methoxycyclohexan-1-one as raw material. Spirotetramat was obtained in an overall yield of 20.4% by a multi-step reaction sequence including hydrolysis, esterification, acylation, intramolecular

Abstract A modified version of the three-component Biginelli reaction of 4-hydroxy-6-methyl-2H-pyran-2-one with aromatic aldehydes and 1H-benzimidazol-2-amine has been studied under thermal and microwave activation. Depending on the substituent in the initial aldehyde, angularly fused 5,6-dihydro-4H-benzo[4,5]imidazo[1,2-a]pyranopyrimidin-4-ones or 2-amino-1H-benzimidazol-3-ium arylbis(4-hydroxy-6

Abstract Successive treatment of potassium 1,1,3,3-tetracyano-2-(2-(methoxycarbonyl)benzoyl)prop-2-enide with concentrated sulfuric acid and water gave 2-(5′-amino-4′-cyano-3-oxo-3H,3′H-spiro[[2]benzofuran-1,2′-furan]-3′-ylidene)propanedinitrile. The reaction of the title compound with sodium hydroxide, followed by neutralization with sulfuric acid afforded 4′-amino-3,3′,6′-trioxo-2′,3′,5′,6′-tetr

Abstract The addition of saturated monobasic C3–C5 carboxylic acids to unsaturated tricyclic ester, tricyclo[5.2.1.02,6]dec-3-en-8-yl propanoate, in the presence of boron trifluoride–diethyl ether complex gave the corresponding tricyclic diesters in 76.8–88.5 wt % yield. The product structure was confirmed by IR and 1H and 13C NMR spectra. The synthesized diesters possess a pleasant odor and can be

Abstract A series of novel coronene-based fluorescent materials have been synthesized through well-defined protocol from 1,2-dimethoxybenzene, with the key steps including Suzuki–Miyaura coupling and oxidative cyclodehydrogenation with ferric chloride. Fluorescence spectra investigations proved that they have emissions in the range λ 460-470 nm with excitation wavelength at λ 373 nm. It is found that

Abstract 3-Phenyl-2-(prop-2-en-1-ylsulfanyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one reacted with 4-methoxyphenyltellurium trichloride in a regioselective manner to give angularly fused 1-{[dichloro(4-methoxyphenyl)-λ4-tellanyl]methyl}-4-oxo-5-phenyl-1,2,4,5,6,7,8,9-octahydrobenzo[4,5]thieno[3,2-e][1,3]thiazolo[3,2-a]pyrimidinium chloride. Electrophilic cyclization of 2-(prop-2-en-1-ylsulfanyl)-

Abstract N-Methyl- and N-benzyl-4H-thieno[3,2-b]pyrrole-5-carboxylic amides containing cytisine, (R)-(+)-α-methylbenzylamine, aniline, and some amino acid fragments have been synthesized.

Abstract Michael adduct of levoglucosenone and cyclohexanone, 1,6-anhydro-3,4-dideoxy-4-C-(2-oxocyclohexan-1-yl)-β-D-erythrohexo-2-ulose, was treated with ethylene glycol in the presence of oxalic acid, and the resulting mixed ketal, 2-{(4a′S,6a′S,10a′R,10b′R)-octahydrospiro[1,3-dioxolane-2,2′-pyrano[2,3-c]chromen]-6a′(1′H)-yloxy}ethanol, was used a chiral auxiliary in the synthesis of vicinal diols

Abstract The alkylation of 5,5′-diaryl-2,2′-biimidazole-1,1′-diols with an equimolar amount of methyl iodide gave the corresponding N-methyl derivatives, and the reaction with 3 equiv of methyl iodide afforded alkylation products at the nitrogen atom and both hydroxy groups. 5,5′-Diaryl-1H,1′H-2,2′-biimidazoles were obtained by treatment of the title compounds with triphenylphosphine.

Abstract The effect of chemical modification of the tetrapyrrole macrocycle structure on the spectral, acid–base, and complexing properties of tetrakis[5,6-bis(4-tert-butylphenyl)pyrazino]porphyrazine, tetra(4-tert-butyl)phthalocyanine, and octakis(4-tert-butylphenyl)porphyrazine in acetonitrile at 298–318 K has been studied by 1H NMR, electronic spectroscopy, and mass spectrometry. The obtained results

Abstract Possible synthetic routes to 4-bromo-1,1′:4′,1″-terphenyl and 4-methyl-1,1′:4′,1″-terphenyl have been studied. Stevens rearrangement of quaternary ammonium salts containing 3-phenylprop-2-en-1-yl and 3-(4-bromo- or 4-methylphenyl)prop-2-yn-1-yl groups gave 1-(4-bromophenyl)-N,N-dimethyl-4-phenylhex-5-en-1-yn-3-amine, 1-(4-bromophenyl)-N,N-diethyl-4-phenylhex-5-en-1-yn-3-amine, 1-(4-bromophenyl)-4-phenyl-N

Abstract Reactions of 5-(1,3-benzothiazol-2-yl)furan-2-carbaldehyde with 2-acetylfuran, 2-acetylthiophene, and some compounds containing an active methylene group gave a number of new 3-[5-(1,3-benzothiazol-2-yl)furan-2-yl]-1-(furan- or thiophen-2-yl)prop-2-en-1-one, 3-[5-(1,3-benzothiazol-2-yl)furan-2-yl]acrylonitrile, 3-[5-(1,3-benzothiazol-2-yl)furan-2-yl]-2-cyanoacrylamide, and 5-{[5-(1,3-benz

Abstract DFT quantum chemical calculations at the B3PW91/6-31G(d) level of theory have shown that the addition of secondary phosphine sulfides and phosphine selenides with alkyl, phenyl, and phenylalkyl substituents to pentyl vinyl and hexyl vinyl selenides follows a molecular mechanism against the Markovnikov rule through energetically favorable eight-membered transition state, leading to the formation

Abstract Heating of 2-halopyridine-3,4-dicarboxylic acids in propionic anhydride led to the formation of 4-halofuro[3,4-c]pyridine-1,3-diones as a result of intramolecular dehydration of the vicinal carboxy groups. The subsequent reduction of 4-halofuro[3,4-c]pyridine-1,3-diones with sodium tetrahydridoborate in THF at room temperature afforded 4-halofuro[3,4-c]pyridin-3(1H)-ones as the major products

Abstract A simple and efficient microwave-assisted protocol has been developed for the synthetic of a series of novel pyrazole–indanone hybrid analogs. The target compounds have been synthesized by the Claisen–Schmidt condensation of different 1,3-diphenyl-1H-pyrazole-4-carbaldehydes with 2,3-dihydro-1H-inden-1-one in the presence of potassium hydroxide. The compounds were characterized by IR, 1H and

Abstract Multicomponent condensation of cyanothioacetamide, 4-fluoro-2-methylbenzaldehyde, methyl 4-methyl-3-oxopentanoate, and 3-(2-bromoacetyl)-2H-chromen-2-one afforded a new heterocyclic system, substituted chromeno[3″,4″:5′,6′]pyrido[2′,3′:4,5]thieno[3,2-e]pyridine. The molecular and crystal structures of the product were determined by X-ray analysis.

Abstract Treatment of peroxide ozonolysis products of the bicyclic monoterpenes (–)-α-pinene and (+)-3-carene with 4-hydroxybenzohydrazide in methylene chloride or tetrahydrofuran gave the corresponding keto acids, whereas keto esters were formed in methanol.

Abstract Treatment of 1,3-benzothiazol-2(3H)-one and its 3-methyl derivative with chlorosulfonic acid afforded the corresponding 2-oxo-2,3-dihydro-1,3-benzothiazole-6-sulfonyl chlorides which reacted with water, alcohols, and amines to give 2-oxo-2,3-dihydro-1,3-benzothiazole-6-sulfonic acids and their esters and amides.

Abstract Electrophilic amination of methyl N-(hydroxyphenyl)carbamates and methyl N-(4-methoxyphenyl)carbamate with sodium azide in 86% polyphosphoric acid (PPA) at 55–60°C regioselectively afforded methyl N-(3-amino-2-hydroxyphenyl)-, N-(4-amino-3-hydroxyphenyl)-, N-(3-amino-4-hydroxyphenyl)-, and N-(3-amino-4-methoxyphenyl)carbamates, i.e., the amino group entered the ortho position with respect

Abstract Maghemite–copper oxide nanocomposite catalyzed oxidative coupling of formamides with β-dicarbonyl compounds in the presence of tert-butyl hydroperoxide as an oxidant to produce the corresponding enol carbamates in excellent yields (up to 92%) under the optimized conditions. The simple preparation and the ability to be recycled and magnetically separated are salient features of this catalytic

Abstract New N-substituted enamino ketones were synthesized by directed transformation of 3-acetyl- and 3-benzoyl-5,6,7,8-tetrafluoro-4H-chromen-4-ones by the action of highly basic primary amines as a result of opening of the pyranone ring and deacylation. The synthesizedN-hexyl and N-octyl derivatives were evaluated for fungistatic and bacteriostatic activities.

Abstract Modification of the isopropenyl group of biologically active azepanobetulin via oxidation with ozone and selenium dioxide, allylic bromination, azidation, amination, reduction, 1,3-dipolar cycloaddition, and Claisen–Schmidt condensation afforded a series of C30-derivatives with oxygen- and nitrogen-containing aliphatic and heterocyclic substituents.

Abstract Treatment of 3-methylcyclohexanone with ethyl formate in the presence of sodium methoxide afforded sodium (2-methyl-6-oxocyclohexylidene)methanolate which reacted with aminopyrazoles, aminotriazole, and aminotetrazole to produce fused quinazoline derivatives; its reactions with cyanothioacetamide, cyanoacetamide, and cyanoacetohydrazide gave tetrahydroquinoline-3-carbonitrile derivatives.

Abstract A new approach has been proposed to the synthesis of optically active 4H-3,1-benzoxazine derivatives based on α-amino acids. The target products have been obtained by reaction of o-(cyclopent-1-en-1-yl)aniline with N-Boc-protected amino acids, followed by removal of the protecting group and heterocyclization by the action of dry hydrogen chloride in methylene chloride.

Abstract 4-(4-Aminophenyl)-2,6-diphenylpyrimidine was synthesized by reaction of (E)-1-(4-aminophenyl)-3-phenylprop-2-en-1-one with benzamidine and was involved in a number of transformations at the amino group, which afforded N-(2,4-dinitrophenyl) and N-acyl derivatives, N-[4-(2,6-diphenylpyrimidin-4-yl)phenyl]-6-methyl-2-(methylsulfanyl)pyrimidin-4-amine, and substituted quinazolines containing a

Abstract A convenient method has been developed for the synthesis of 3,5-bis(hydroxymethyl)adamantan-1-ols via successive nitroxylation of 1,3-bis(acetoxymethyl)adamantanes with fuming nitric acid, alkaline hydrolysis of intermediate 3,5-bis(acetoxymethyl)adamantane-1-yl nitrates, and reaction of the resulting 3,5-bis(hydroxymethyl)adamantan-1-yl nitrates with hydrazine hydrate. 3,5-Bis(hydroxymethyl)adamantan-1-ols

Abstract Reactions of 3-(furan-2-ylmethyl)-2-sulfanyidene-1,3-thiazolidin-4-one with aromatic and heterocyclic aldehydes afforded a series of previously unknown 5-[(het)arylmethylidene]-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-ones. Treatment of 3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one with thionyl chloride gave in a good yield 3,3′-bis(furan-2-ylmethyl)-2,2′-disulfanylidene-5

Abstract Acylation of 4-substituted 4H-thieno[3,2-b]pyrrole-5-carbohydrazides with chloroacetyl chloride, dichloroacetyl chloride, and methacryloyl chloride afforded the corresponding mixed bis-acylhydrazines. Likewise, the reaction of 4-benzyl-4H-thieno[3,2-b]pyrrole-5-carbonyl chloride with ethyl 5-(hydrazinocarbonyl)pyridine-2-carboxylate gave ethyl 5-[2-(4-benzyl-4H-thieno[3,2-b]pyrrole-5-carb

Abstract A new and convenient protocol has been proposed for the transformation of aldoximes to nitriles using trifluoromethanesulfonic anhydride and triethylamine. The proposed method allows a range of aldoximes, including aromatic, heterocyclic, aliphatic, and cycloaliphatic aldoximes, to be converted to the corresponding nitriles in good to excellent yields.

Abstract A series of novel 3H-benzo[f]chromen-3-one derivatives bearing non-steroidal anti-inflammatory drug moieties were synthesized with good yields. Benzo[f]coumarin chalcone was prepared via Claisen–Schmidt condensation between 2-acetyl-3H-benzo[f]chromen-3-one and 4-hydroxybenzaldehyde in basic medium and was then esterified with carboxylic acids (drugs) in the presence of phosphoryl chloride

Abstract New methods have been developed for the synthesis of previously unknown ω-(hexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetradecan-10-exo-yloxy)alkan-1-ols and hexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetradecan-10-exo-yl carboxylates by reactions of heptacyclo[8.4.0.02,12.03,8.04,6.05,9.011,13]tetradecane (binor-S) with α,ω-diols and organic acids in the presence of inorganic ionic liquids at 120–150°C

Abstract Methionine-coated Fe3O4 nanoparticles, a magnetically reusable and environmentally friendly heterogeneous catalyst, was synthesized. The new catalyst was characterized by FT-IR spectra, XRD, SEM, and EDX analysis and was used to catalyze the cycloaddition of nitriles and sodium azide in DMSO at 120°C to give the corresponding 5-substituted 1H-tetrazoles. Methionine-coated Fe3O4 nanoparticles

Abstract The reaction of pyrrolo[3,2,1-ij]quinoline-1,2-diones with methyl (het)aryl ketones gave the corresponding 1-(het)arylmethylidenepyrroloquinolin-2-ones, and 1,3-dipolar cycloaddition of the latter to azomethine ylide generated from sarcosine and paraformaldehyde afforded 4-acyl-1,4′,4′,6′-tetramethylspiro[pyrrolidine-3,1′-pyrrolo[3,2,1-ij]quinolin]-2′(4′H)-ones. The synthesized compounds were