Search

A commercially scalable five-step synthetic process starting from cis/trans (7:3) mixture of dimethyl 1,4-cyclohexanedicarboxylate is devised for preparation of tranexamic acid with more than 99.5% purity. All impurities are controlled as per monograph. 47% overall yield over five steps has been achieved based on recovery. Epimerization of a cis-predominant isomeric mixture to trans predominant isomeric mixture under mild conditions followed by exploiting the difference in solubility to obtain trans isomer in very high purity is the key feature of the synthesis. In addition to this, use of readily available and cost efficient raw materials/reagents, recycling of cis isomer, explicit design of downstream processing enabling the retention of the trans-stereochemistry until final API are some of the highlights of this synthesis. This process also circumvents the use of hazardous chemicals and harsh reaction conditions making it greener and safer compared to the previous reports." [ABSTRACT FROM AUTHOR]

Sugar nucleotides are essential substrates used for synthesizing bioactive oligosaccharides in enzymatic reactions, however, their preparation via chemical and enzyme reactions is challenging. Therefore, we investigated the synthesis of sugar nucleotides under optimal conditions using a facile one-step reaction. Seven sugar nucleotides were synthesized via an optimized one-step reaction in 40–80% yield, exhibiting a preference for 1,2-trans glycoside. Moreover, a gram-scale synthesis of UDP-galactose resulted in a 46% (578 mg) yield. [ABSTRACT FROM AUTHOR]

The Doebner reaction is the chemical reaction of an aniline with an aldehyde and pyruvic acid to form quinoline-4-carboxylic acids. Although Doebner reaction is a simple procedure for synthesis of 4-carboxyquinolines, which the product precipitates from the reaction mixtures with high purity, its yield is not high due to the formation of different reaction by-products. In the present study we found a new by-product (2-methylquinoline-4-carboxilic acid derivative), in Doebner reaction. We synthesized new 2-methylquinoline-4-carboxilic acid derivatives simply by stirring pyruvic acid and aromatic amine in ethanol with high purity. Generally, we found that aniline derivatives possessing electron donating groups are needed for the synthesis of 2-methylquinoline-4-carboxilic acid derivatives in ethanol. 1H-NMR data of products revealed that this reaction is regioseletive and ring closure occurs on the position with less steric hindrance. The order of mixing of the reactants plays a key role in determining the type of products in the Doebner reaction. [ABSTRACT FROM AUTHOR]

An electrochemical oxidative iodination of imidazo[1,2-a]pyridines is achieved in this study. This reaction utilizes NaI as an iodine source and a supporting electrolyte under metal-free and exogenous chemical oxidant-free reaction conditions. The present protocol provides an efficient route to prepare 3-iodoimidazo[1,2-a]pyridines derivatives. [ABSTRACT FROM AUTHOR]

Benzyl imidazole was successfully lithiated using n-BuLi at −78 °C and verified by deuterium incorporation. The chemical reaction of the lithiated benzimidazole was explored with a series of different electrophiles. This approach was utilized to synthesize new anti and syn diphenyl organocatalysts for trans-diol functionalization. [ABSTRACT FROM AUTHOR]

In an attempt to further exploit multicomponent reactions in the field of 1,4 naphthoquinone-based compounds, we describe an Ugi-type multicomponent approach for the synthesis of novel 3-substituted 1,4 naphthoquinone molecules. The process relies on the execution of an enol-Ugi reaction between an enol-3-nitro-1,4 naphthoquinone with different secondary diamines and isocyanides. The novel methodology showed great chemical efficiency and versatility. [ABSTRACT FROM AUTHOR]

An efficient tandem route to obtain novel spiro[indazolo[3,2-b]quinazoline-7,3′-indolines has been explored. The one-step domino reaction proceeds via in situ generation of the 1H-indazol-3-amines followed by its reaction with the cyclic 1,3-dicarbonyls and isatin derivatives to furnish complex N-fused spiro-polyheterocyclic frameworks. This protocol describes a valuable route to concisely and feasibly obtain spiro[indazolo[3,2-b]quinazoline-7,3′-indolines from isatin derivatives. The present protocol is particularly attractive because of the following features: group-assisted-purification (GAP) chemistry process, low-cost solvent, convenience of operation, excellent atom economy, and high yields. [ABSTRACT FROM AUTHOR]

A facile method to synthesize 2-nitromethyl aromatic ketones was developed. In the method, benzyne was generated in situ for the insertion to α-Nitroketones in one pot to achieve 2-nitromethyl aromatic ketones under mild conditions. Aromatic and aliphatic α-nitroketones were applied in the reaction, and the results show that aliphatic α-nitroketones gave excellent yields (up to 96%), while aromatic α-nitroketones gave moderate yields. The synthesized 2-nitromethyl aromatic ketones could be potential substrates to synthesize isoindoles. [ABSTRACT FROM AUTHOR]

The chemical reactivity of 3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (1) towards some phosphorus reagents was studied. The enaminone 1 was cyclized into diethyl 2-phosphonochromone 2 via its treatment with diethyl phosphite in basic medium. However, its reaction with triethoxy phosphonoacetate gave the substituted pyrone phosphonate 3. In addition, two novel examples of 4-(dimethylamino)-6-(2-hydroxyphenyl)-2-sulfido-4H-1,3,2-oxathia-phosphinines 6 and 7 were obtained from treatment of enaminone 1 with O,O-diethyl dithiophosphoric acid and Lawesson's reagent. When enaminone 1 was also treated with phosphorus decasulfide, it was turned into 4H-thiochromene-4-thione while its treatment with phosphorus tribromide, phosphorus oxychloride, or phenylphosphonic dichloride, 4H-4-oxo-chromene was isolated in all cases. The possible reaction mechanisms of the formation of these products were discussed. The structures of newly isolated products were established by elemental analysis and spectral tools. [ABSTRACT FROM AUTHOR]

Morita-Baylis-Hillman adducts, prepared from 2-nitrobenzaldehyde precursors and either methyl acrylate or methyl vinyl ketone, have been used as critical synthons in the preparation of α-[(alkylamino)methyl]cinnamate esters and their but-3-en-2-one analogs, cinnamate ester-azidothymidine (AZT) conjugates, 2-quinolone and quinoline derivatives. Computer docking studies have been conducted to explore the potential of the cinnamate ester-AZT conjugates as potential dual-action HIV-1 integrase-reverse transcriptase (IN-RT) inhibitors. The results further demonstrate the applicability of Morita-Baylis-Hillman methodology in the construction of complex drug-like scaffolds. [ABSTRACT FROM AUTHOR]

A series of spirocyclohexane-1,4′-pyrazolothiazepinones were synthesized by one-pot multicomponent cyclocondensation reactions between 5-amino-1-arylpyrazoles, cyclohexanone and mercaptoacetic acid with good yields and easy purification protocols. Some control experiments involving isolation of reaction intermediates were performed leading to the proposal of three alternative mechanistic pathways conducting to the named spiroheterocycles. All target molecules were fully characterized by IR, NMR, melting point and HRMS. [ABSTRACT FROM AUTHOR]

The synthesis of a library of 2,6-disubstituted-azaindoles relying on Sonogashira cross-coupling and intramolecular cyclization is described. Eleven examples of 6-alkynyl derivatives and three examples of 3-bromo-5-azaindoles are reported. One of the 3-bromo-5-azaindoles was also further functionalized with two different aryl trifluoroborate salts via Suzuki-Miyaura coupling reaction. [ABSTRACT FROM AUTHOR]

Heterocyclic imines provide biaryl products by a two-step transformation. The first transformation involves a Diels-Alder reaction with a multiply protonated imine to give a tetrahydroquinoline product, whereas the second step involves oxidation with elemental sulfur at 260 °C. [ABSTRACT FROM AUTHOR]

Benzoxazinoids (BXs), alkaloids frequently found in Gramineae species, are natural defensives that can potentially be exploited to the development of novel antimicrobial agents. Here, BXs analogs were synthesized from 2-nitrophenol (benzoxazinone series) and 3-hydroxy-2-nitropyridine (pyridoxazinone series) and tested against fungal and bacteria of medical interest. The starting materials were submitted to adequate nucleophilic substitution in order to functionalize of analogs, followed by a reductive cyclization catalyzed by palladium on carbon. Next, the biological assays showed that pyridoxazinone serie has a good antibacterial activity, especially against Enterococcus faecalis (Minimum inhibitory concentration—MIC: 7.8-15.6 μg.mL−1) and Acinetobacter baumannii (MIC 31.25-125 μg.mL−1). Antifungal activity, in turn, was related to compound 2e which showed a MIC of 62.5 μg.mL−1 against Candida albicans, Candida glabrata, and Candida tropicalis. All analogs complied with Lipinski's rules and were predicted to have a low toxicity. [ABSTRACT FROM AUTHOR]

Facile and efficient synthesis of sulfoxide esters using menthols as chiral auxiliary is described. Phenylthio/benzylthio/naphthylthioacetic esters act as an efficient substrate for chiral sulfoxides via oxidation in one step. The structural and stereochemical aspects of target product were established on the basis of various spectroscopic studies, namely FT-IR, NMR (1H NMR and 13C NMR) and elemental analysis. This method is simple, fast, convenient and very efficient. [ABSTRACT FROM AUTHOR]

The present work emphasizes on a green methodology using designed and synthesized basic ionic liquid, [n-butyl Urotropinium]OH, and commercially available aqueous solution of choline hydroxide [Ch]OH as catalysts for executing Aza-Michael addition of N-heterocycles to α,β-unsaturated compounds at room temperature. The highlighting features of these catalysts include using low concentration of both catalysts along with [Ch]OH being low cost and biodegradable, [n-butyl Urotropinium]OH significantly enhancing the high substrate/catalyst ratio to obtain the desired products in high yield and purity in most cases. Further, both catalysts were recyclable and recoverable up to five cycles. [ABSTRACT FROM AUTHOR]

Piperlotines are natural products characterized by an α,β-unsaturated amide moiety. These compounds found wide applications in Medicinal Chemistry like antibacterials, cytotoxic agents, anticoagulants, among others. To date, diverse methods of synthesis have been reported for piperlotines, but involving the use of catalysts, hazard reagents, anhydrous media or coupling reagents. Thus, in this work, we developed a greener method of synthesis of piperlotines A, C, and derivatives, through mechanochemical activation under solvent-free conditions. The reaction of a β-amidophosphonate, K2CO3, and an aromatic aldehyde afforded target compounds in moderate to good yields (46-77%), in an open atmosphere by grinding. It is worth to mention that this mechanochemical process was under thermodynamic control because just E isomer was isolated for every reaction. Moreover, synthesized piperlotines have been predicted by means of chemoinformatic analysis as potential therapeutic agents for the treatment of arthritis or cancer. [ABSTRACT FROM AUTHOR]

A new class of phenethylamine-derived tridentate P,N,N-ligands has been successfully developed. These ligands exhibited good performance in the Ir-catalyzed asymmetric hydrogenation of β-keto esters, affording the corresponding β-hydroxy esters in moderate to good enantioselectivities. [ABSTRACT FROM AUTHOR]

A solution phase method was adopted for the synthesis of proline-containing cyclic pentapeptide 2 and total synthesis of naturally occurring cyclic heptapeptide Reniochalistatin B 3. For the synthesis of 3, both divergent and convergent strategies were used to improve the overall yield from 12 to 25%. Different N and C terminal modified linear analogs and congeners of 2 and 3 were synthesized. Both cyclic peptides 2 and 3 and their linear analogs/congeners were evaluated for anti-cancer activity against HeLa cell line, among which pentapeptide 2 h and hexapeptide 3n with N-terminal protected hexafluoroisopropyl carbamates (HFIPC) interestingly showed higher cytotoxicity with an IC50 of 2.73 and 4.3 µM, respectively compared to their Boc-protected analogs 2a (IC50 20 µM) and 3c (IC50 38.51 µM) and cyclic peptides 2 (>100 µM) and 3 (47 µM). These results were further validated by biological experiments such as colony formation and wound healing assays. [ABSTRACT FROM AUTHOR]

In the present study, the reactions of p-chloranil (1a) and 2,3-dichloro-1,4-naphthoquinone (DCNQ) (1b) with some aryl phenols were investigated. The structures of all compounds were characterized using spectroscopic methods (FT-IR, 1H NMR, 13C NMR, and MS) and microanalysis. The electrochemical behaviors of some benzoquinone and naphthoquinone derivatives have also been investigated in unbuffered aprotic solutions. [ABSTRACT FROM AUTHOR]

Sonogashira cross coupling is a well-known reaction for the formation of carbon-carbon bond. It involves the coupling of aryl halides with terminal alkynes to synthesize versatile functionalized alkyne scaffolds having diverse applications. Many of the natural products and important pharmaceutical drugs can be obtained through this reaction. In this regard, hectic progress has been put by the synthetic chemists to make this cross coupling more effective. This review article discloses mild and environmental friendly reaction conditions of Sonogashira cross coupling developed during 2013-2018. [ABSTRACT FROM AUTHOR]

N-acylation of substituted sulfonamides with different anhydrides in the presence of Cesium salt of Wells-Dawson heteropolyacid (Cs5HP2W18O62) as an efficient and reusable catalyst was investigated for the first time.  Cs5HP2W18O62 was used with a catalytic amount in water as a green solvent. At room temperature, a series of N-acylsulfonamides were synthesized, while under refluxing conditions, new cyclic imides containing sulfonyl group were obtained. Atom-economy, high yields, easy work-up, as well as simple catalyst recovery and reusability are the key features of this procedure. [ABSTRACT FROM AUTHOR]

A facile synthesis of 2,3-disubstituted benzofurans from ortho oxyether aroylformates has been developed. Under the mediation of DBU, the intramolecular annulation of ortho oxyether aroylformates proceeds smoothly to provide the corresponding 2,3-disubstituted benzofurans in moderate to good yields under mild conditions. Furthermore, a one-pot two-step synthesis of 2,3-disubstituted benzofurans has also been demonstrated from readily available ortho hydroxy aroylformates. [ABSTRACT FROM AUTHOR]

1,2- and 2,1-benzothiazines, for example, 1,2-benzothiazine-1,1-dioxides. 2,benzothiazine-2,2-dioxides, 1-alkyl/aryl-1,2-/2,1-benzothiazine-S-oxides, dibenzothiazine and polyheterocycle containing benzothiazine moiety are considered to be one of the privileged heterocyclic scaffolds with huge importances both in synthetic organic chemistry and medicinal chemistry especially in the drug industry. Numerous pioneering methodologies for asymmetric and non-asymmetric scaffold constructions have been developed. Comprehensive visions of different powerful methodologies for the synthesis of these scaffolds have been presented in this review. [ABSTRACT FROM AUTHOR]

A highly efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes has been developed that proceeds smoothly under mild and neutral conditions and provides a general and practical route for the synthesis of a variety of α-halomethyl ketones with high atom-economy, excellent yield, and recyclability of the gold(I) catalyst. The presented method delivers an attractive alternative to classical α-halogenation of ketones. [ABSTRACT FROM AUTHOR]

A series of β‐hydroxyazides were effectively synthesized from the regioselective ring opening of epoxides by sodium azide using montmorillonite K10 as a novel heterogeneous catalyst in aqueous acetonitrile in good to excellent yields. The utility of this method has been demonstrated by achieving a short synthesis of phenylglycine in 33.5% overall yield. [ABSTRACT FROM AUTHOR]

2-(3-Cyano-5-hydroxy-4,5-dimethyl-1H-pyrrol-2(5H)-ylidene)malononitrile was synthesized by the interaction between malononitrile dimer and diacetyl. It reacts with aldehydes in ethanol in the presence of ammonium acetate at room temperature and results 2-(3-cyano-5-hydroxy-5-methyl-4-vinylene-1H-pyrrol-2(5H)-ylidene)malononitriles in 66-86% yield. The developed method is of interest as a promising approach to a novel group of push-pull chromophores, which are functionalized analogs of widely used chromophores of the tricyanofuran (TCF) series.GRAPHICAL ABSTRACT [ABSTRACT FROM AUTHOR]

The first example of recyclable Zn(ANA)2Cl2 catalyzed tandem one-pot three-component protocol reaction between aromatic aldehydes, malononitrile, and phenylmethylpyrazolone to furnish 4-substituted-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (4a-l) in a short reaction time (∼10 min) in aqueous media at room temperature is described. [ABSTRACT FROM AUTHOR]

An efficient solvent-free access towards highly substituted pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine-3-carbonitrile derivatives has been established through multi-component reaction of 1H‐pyrazolo[3,4‐b]pyridin‐3‐amine, aldehyde, 3-(1H-indol-3-yl)-3-oxopropanenitrile catalyzed by 1,1,3,3-tetramethylguanidine (TMG). The reaction allows the formation of one C−C and two C−N bonds with high yield. The significant features of this solvent-free reaction include mild reaction condition, readily accessible substrates, short reaction time, excellent yield, and broad substrate scopes as well as simple one-pot operation, no column chromatographic purification, which makes this strategy highly attractive. [ABSTRACT FROM AUTHOR]

Cyclization of 2-aryl amides with base lead to quinolone derivatives. Both graveoline and graveolinine were synthesized.GRAPHICAL ABSTRACT [ABSTRACT FROM AUTHOR]

In the presence of I2, a simple method for the preparation of arylselanyl anilines from anilines and diselenides is developed. This metal-free iodine-promoted procedure proceeds efficiently under mild reaction conditions, providing a series of arylselanyl anilines with high regioselectivity, and mostly in moderate to good yields. [ABSTRACT FROM AUTHOR]

In this article, we report the approach to the substituted ureas based on the reaction of 1-(3,3-diethoxypropyl)ureas with phenols. Depending on the nature of the phenol and urea the reaction leads either to diarylpropane and dibenzoxanthene derivatives or calixarenes. The proposed method benefits from mild reaction conditions, high product yields and operational simplicity. [ABSTRACT FROM AUTHOR]

3-Aminopyrrolidine building block was used as the intermediate for many pharmaceutically active substances. Starting from L-aspartic acid, optically active (S)-tert-butyl-3-aminopyrrolidine-1-carboxylate was synthesized, and the reaction conditions were optimized in each step. The procedure of each step was discussed in detail and could be useful for the industrial preparation. This process was featured by readily available starting material, mild reaction conditions, easy work-up, and economy. [ABSTRACT FROM AUTHOR]

Reliable reactions for the synthesis of two interesting anthracenetetrones have been identified and optimized. Both syntheses start from dihydroxy-9,10-anthraquinones and were selected for maximized efficiency and minimized workload. Work-up of all reactions can be achieved without column chromatography, which facilitates further scale-up. So far, both target compounds are considerably underexplored despite their promising molecular structure for use in devices and in organic synthesis, especially as building blocks for π-conjugated compounds. The crystal structure of 1,4,5,8-anthracentetrone is reported. [ABSTRACT FROM AUTHOR]

A general method is presented for the preparation of homochiral 3-hydroxy fatty acid nicotinyl ester. The pyridine moiety of the esters strongly moderates the reactivity of the borane. Incomplete conversion, however, was overcome by Lewis acid catalysis. Additionally, his structural element seems to be responsible for an improvement of the enzymatic resolution compared to the respective alkyl esters. The resolved enantiomers will be the basic material for liposome building molecules of different chirality. [ABSTRACT FROM AUTHOR]

An efficient and eco-friendly procedure for the synthesis of 2-amino-5-oxo-4-aryl-4H,5H-pyrano[3,2-c]chromene-3-carboxamide has been developed through a one-pot three-component condensation of 4-hydroxycoumarin with aldehydes and cyanoacetamide, in the presence of catalytic amount of polystyrene-supported p-toluenesulfonic acid (PS-PTSA) as a highly active and reusable heterogeneous acid catalyst in EtOH at 80 °C conditions. This new procedure offers several advantages such as shorter reaction times, excellent yields, a wide range of functional group tolerance, easy experimental work-up procedure, operationally simple under metal-free reaction conditions and C-C/C-O bond formation. The catalyst can be recovered and reused for at least four runs without any significant impact on the product yields. [ABSTRACT FROM AUTHOR]

A series of novel 6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives were obtained in good yields from ethyl 4,4,4-trifluoro-3-oxobutanoate, urea, and aryl aldehyde via Biginelli multicomponent reaction. All the corresponding products 4a-4p were examined against four human cancer cell lines (A549, HepG2, COLO205 and DU145) and compounds 4e, 4i, and 4 m which showed promising anticancer activity have been identified. [ABSTRACT FROM AUTHOR]

A simple and general method for the synthesis of new imidazopyridines bearing an aminopyridinyl, chromenyl, or quinolinyl moiety in the C2 position was developed. The Knoevenagel reaction between imidazo[1,2-a]pyridine-2-carbaldehyde 1 and malononitrile resulted in the formation of starting material 2. Subsequently, intramolecular cyclization between the cyano group of 2 and acetophenones, naphtols, hydroxyquinolines, or phenols, gave 3, 4, 5, and 6 compounds, respectively. This is a simple, reproducible, and environmentally friendly method of synthesizing substituted imidazopyridines using water as a solvent or under solvent-free conditions. [ABSTRACT FROM AUTHOR]

In situ generated 2,4-diaryl substituted münchnones from 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido)acetic acids react with acetic anhydride in the presence of 2-nitromethylene thiazolidine, which is most likely acting as a base, and unexpectedly undergo a Dakin-West type reaction and a concurrent autoxidation reaction leading to the formation of (E)-1-(N,4-dimethylbenzamido)-1-(4-fluorophenyl)prop-1-en-2-yl acetate, 4-substitutedphenyl-N-methyl-N-(4-substitutedbenzoyl) benzamides and p-substituted benzoic acids. In addition, a novel and efficient access to N-acyl urea derivatives is described by the reaction between 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido)acetic acids and cyclohexyl, isopropyl carbodiimides in the presence of a base. The structures of all new products were identified on the basis of NMR and IR spectra, along with X-ray diffraction data and HRMS measurements. [ABSTRACT FROM AUTHOR]

Photochemical mediated synthesis in organic chemistry is a highly expanding area. This is a widely exploited area of research for the construction of new pharmaceutically significant heterocycles. Recently many reports appeared for the synthesis of heterocycles photochemically due to a wide range of biological activities associated with them. In this article, I have described the synthesis of a number of oxygen-bearing five-membered heterocycles. [ABSTRACT FROM AUTHOR]

Microwave-assisted green approach is developed for an efficient synthesis of thiazol-2-imines under catalyst-free conditions. The desired products are formed by one-pot three-component reaction which is an improvised method for Hantzsch thiazole synthesis. The microwave-assisted protocol gives excellent yields with high purity in just 10-15 min. All the synthesized compounds have been screened for antifungal activity and some of the derivatives show a broad spectrum against fungal pathogens. [ABSTRACT FROM AUTHOR]

Unexpected formation of β, meso-directly linked diporphyrin products has been described in the reactions of β-formyl porphyrins with pyrrole under Adler-Longo reaction conditions. Preliminary mechanistic studies indicates that β-dipyrromethane substituted porphyrin structure is the crucial intermediate for the formation of diporphyrin product. [ABSTRACT FROM AUTHOR]

A simple and efficient synthesis of 6-substituted 2-(4-aryl-1,2,3-triazol-1-yl)pyrimidines and 7-deazapurines from readily available 6-chloro-2-methylthiopyrimidine and 6-chloro-2-methylthio-7-deazapurine derivatives is described. The synthetic strategy is based on sequential reactions: substitution of 6-chlorine group with amines or (2-pyridyl)tributylstannane, oxidation of the obtained 6-substituted 2-methylthiopyrimidines, and 7-deazapurines to the corresponding 2-methylsulfonyl derivatives, their conversion to 2-azido derivatives and Cu(I)-catalyzed azide − alkyne cycloaddition reaction with arylethynes. [ABSTRACT FROM AUTHOR]

An efficient method for direct α-sulfonyloxylation of various sterically hindered 1,3-dicarbonyl compounds has been developed under mild reaction conditions. The yields of desired products is up to 90% and a plausible mechanism was accordingly proposed. [ABSTRACT FROM AUTHOR]

Many naturally occurring 5-ethylidenehydantoins and their derivatives exhibit extensive biological activities; this characteristic has inspired us to prepare analogues. Fourteen such analogues with the core structure of 5-ethylidenehydantoin were synthesized from readily available components with yields of up to 82%. [ABSTRACT FROM AUTHOR]

An iron(III)-catalyzed protocol towards 2-sulfonyl quinolines from quinoline N-oxides and sodium sulfinates was herein illustrated. The general and direct option featured for high efficiency (up to 91% yields) and good functional compatibilities (27 examples) in the Fe(III)-catalysis. Moreover, free radical mechanism was proposed for the one-pot deoxygenation and sulfonylation reaction based on the results of the control reactions. [ABSTRACT FROM AUTHOR]

A simple and efficient synthesis of 6-substituted 2-(4-aryl-1,2,3-triazol-1-yl)pyrimidines and 7-deazapurines from readily available 6-chloro-2-methylthiopyrimidine and 6-chloro-2-methylthio-7-deazapurine derivatives is described. The synthetic strategy is based on sequential reactions: substitution of 6-chlorine group with amines or (2-pyridyl)tributylstannane, oxidation of the obtained 6-substituted 2-methylthiopyrimidines, and 7-deazapurines to the corresponding 2-methylsulfonyl derivatives, their conversion to 2-azido derivatives and Cu(I)-catalyzed azide − alkyne cycloaddition reaction with arylethynes. [ABSTRACT FROM AUTHOR]

The investigation for replacement of organic solvents in organic synthesis is a growing area of interest due to increasing environmental issues. The use of ionic liquid salts as solvents and catalysts in organic reactions has gained extensive interest. Ionic liquids provided a new environmentally benign and improved alternative to traditional methods in modern synthetic chemistry. The aim of present review is to focus on the applications of ionic liquids for the synthesis of O-heterocycles. [ABSTRACT FROM AUTHOR]

Coumarins units have recently emerged as a hot topic of research due to their diverse applications. Their synthesis is partly based on classical methodologies such as Pechmann reaction or Knoevenagel condensation, but it also sparked the discovery of completely new pathways. In very recent years so-called vertically expanded coumarins were synthesized, effectively expanding the portfolio of existing architectures. This review serves as a guide through synthesis strategies to coumarins. [ABSTRACT FROM AUTHOR]

Phenacyl bromides are used as a building blocks in synthetic organic chemistry, which serves as a key model for the development of various biologically important heterocyclic compounds and other industrially important scaffolds. This review covers recent synthetic advances in the preparation of heterocyclic compounds utilizing various phenacyl bromides. A wide range of five- and six-membered heterocyclic compounds as well as fused heterocyclic compounds were synthesized efficiently from the phenacyl bromide precursors through one-pot multicomponent reactions. [ABSTRACT FROM AUTHOR]