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[Display omitted] • Novel approach for seven-membered benzazepinone core of tolvaptan. • First report on the synthesis of tolvaptan by haloamine cyclization. • Inexpensive starting materials. • Concise synthesis of benzazepinone. • Improved yield of (S)-tolvaptan. A novel and concise approach has been developed for the total synthesis of (S) - tolvaptan, which is used for the treatment of hyponatremia. The key intermediate, benzazepinone has been synthesized in three steps through ortho -acylation of N -Pivalamide protected aryl amine followed by an intramolecular haloamine cyclization. The total synthesis of (S) - tolvaptan from p -chloroaniline has been accomplished in seven steps with 43% overall yield. [ABSTRACT FROM AUTHOR]

[Display omitted] A highly efficient telescopic synthesis of a nitrogen-fused heterocycle dihydrodibenzonapthyridinedione has been developed via imine formation, then the Castagnoli-Cushman reaction followed by nitro-reduction and intramolecular lactamization starting from 2-nitrobenzaldehyde, aliphatic/aromatic amines, and homophthalic anhydride. This one-pot stepwise synthesis strategy offers a practical and simple approach to produce structurally diverse dihydrodibenzonaphthyridinediones without isolating intermediates. [ABSTRACT FROM AUTHOR]

• Myo-inositol, a cardiovascular medicine, was used as tridentate O -donor ligand for Cu-catalyzed amination reaction in water. • The C N coupling reaction of aryl halides with amines were achieved by Cu powder/myo-inositol catalytic system. • The broad scope of substrates was participated in the coupling. Myo-inositol is originally applied as a cardiovascular medicine in clinic, which can be multi-ton manufactured via extraction from the byproducts in agricultural product processing such as defatted rice bran and corn-soaking water. Herein, the application of myo-inositol (MI) as a novel versatile tridentate O -donor ligand has been first described for promoting Cu-catalyzed amination reaction in aqueous medium. [ABSTRACT FROM AUTHOR]

A- and d -ring modified luotonin-inspired heterocyclic systems have been synthesized starting from phenylalanine following a six-step route that includes the final key stage an intramolecular Povarov reaction. • A- and D-ring modified luotonin-inspired heterocyclic systems have been synthesized. • The six-step route that starts from phenylalanine has the final key stage an intramolecular Povarov reaction. • The synthesized analogues with reduced planarity were characterized by spectroscopic studies. A small library of A- and D-ring modified luotonin-inspired heterocyclic systems have been synthesised in moderate to good yields following a six-step route that starts from phenylalanine and has the final key stage an intramolecular Povarov reaction of imines obtained from a tetrahydroquinoline-derived alkynyl aldehyde and various arylamines. [ABSTRACT FROM AUTHOR]

• A novel [(NHC)NiCpCl] complex was synthesized and successfully applied to a Ni catalyzed Chan-Lam coupling. • A well-defined NHC-Ni complex aptly catalyzed Chan-Lam coupling of aryl- and alkyl-amines. • 4,4′-Dimethyl-2,2′-bipyridine was a useful co-ligand to make the developed Ni catalysis highly effective. In this study, a well-defined, novel NHC-Ni complex was developed and used to catalyze the N -arylation of alkyl- and arylamines with arylboronic acids in a rare version of Chan-Lam coupling. Although the same coupling using copper catalysts has been widely studied, the nickel-catalyzed version is rare and normally requires 10–20 mol% catalyst loading. This novel NHC-Ni complex in combination with 4,4′-dimethyl-2,2′-bipyridine, however, proved to be an effective catalyst that lowered the required catalyst loading to only 2.0 mol%. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • Metal-free conversion of alkynes into secondary amines. • One-pot three-step process. • Atom-, step-economy. Abstract A metal-free one-pot synthesis of secondary amines from aryl alkynes via hydration-condensation-reduction three-step process in the presence of TfOH and B 2 (OH) 4 has been developed. A series of secondary amines were obtained with good functional group tolerance and satisfied yields. [ABSTRACT FROM AUTHOR]

[Display omitted] Methods of copper-catalyzed alkylation of indoles and anilines with tertiary alkyl bromides were reported. These protocols provided various N - tert -alkyl 3-substituted indoles and electron-deficient N - tert -alkyl anilines in moderate to good yields via C N coupling. [ABSTRACT FROM AUTHOR]

[Display omitted] A novel methodology for the primary amination of aromatic C(sp2)-H bond utilizing hydroxylamine derivative as ammonia surrogates has been developed. With a cost-effective and convenient copper oxide, a variety of aromatic primary amines were synthesized without external oxidant with moderate to good yields under the mild conditions. This amination exhibits excellent functional group tolerance, wide substrate scope, the use of readily available substrates, and a facile work-up procedure. Furthermore, the late-stage modification of drug-like small molecules with complex structures was also allowed. [ABSTRACT FROM AUTHOR]

An efficient method was developed for the synthesis of N -arylhexaoxazadispiroalkanes by the ring transformation of heptaoxadispiroalkanes with arylamines in the presence of lanthanide salts as catalysts. [ABSTRACT FROM AUTHOR]

A facile protocol for the synthesis of acridone derivatives has been developed through palladium-catalyzed carbonylation/C H activation sequence from 2-bromo-diarylamines in moderate to excellent yields. The reactions occurred smoothly and allowed both electron-rich and electron-deficient substrates converted to the corresponding acridones. [ABSTRACT FROM AUTHOR]

The Buchwald-Hartwig Pd-catalyzed C-N coupling reaction of 5-substituted 3-chloro-4 H -1,2,6-thiadiazin-4-ones with primary (het)arylamines is described, affording twenty new 3,5-disubstituted 4 H -1,2,6-thiadiazin-4-ones in 56–99% yield. The protocol enables the mild preparation of difficult to access 3,5-dianilino-1,2,6-4 H -thiadiazin-4-ones. The reaction scope and limitations are discussed. [ABSTRACT FROM AUTHOR]

An efficient and catalyst-free for the synthesis of 1,2,4,5-tetrasubstituted imidazoles has been developed using a one-pot, two-step reaction of arylamins, benzonitriles, arylglyoxals, and Meldrum’s acid. All the products were obtained in good to excellent yields and their structures were established from their spectroscopic data. [ABSTRACT FROM AUTHOR]

Photoredox-catalyzed radical reactions have attracted intense interest from synthetic chemists over the past several years. The photoredox-catalyzed C(sp 2 )–N coupling reactions, including Ullmann type C–N coupling (C–X/N–H type coupling), redox neutral C–N coupling (C–H/N–X type coupling) and oxidative C–N coupling (C–H/N–H type coupling), have been summarized in this digest. [ABSTRACT FROM AUTHOR]

A novel and green synthesis of 2-((2-aryl-3-oxoisoindolin-1-yl)methyl)quinazolin-4(3 H )-one is described. The one-pot three-component reaction between 2-methylquinazolin-4(3 H )-ones, aryl amines and 2-formylbenzoic acid, through a sequential condensation, sp 3 C H bond functionalization and cyclization reactions in aqueous media leads to formation of desired compounds in good to excellent yields. [ABSTRACT FROM AUTHOR]

We herein report a serendipitously observed acid mediated rearrangement of monoethylene ketal of 2-methyl-2-(3-methylbut-2-en-1-yl)cyclohex-4-ene-1,3-diones to Dihydrobenzopyran and demonstrated the application of this methodology in the construction of core carbon scaffolds of dimethoxyajacareubin, cariphenone-A and crotamadine. [ABSTRACT FROM AUTHOR]

A new class of 2-arylamino-dihydroxyindenopyrroles were prepared by the one-pot multicomponent reaction of ninhydrin, N -methyl-1-(methylthio)-2-nitroethenamine and aromatic amines in EtOH at room temperature. The advantages of this procedure are short reaction times, good to high yields, easy separation of products and good functional group tolerance. [ABSTRACT FROM AUTHOR]

An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the N C bond in isocyanates, reacted with aryne precursors to afford various aniline derivatives in moderate to excellent yield and tolerated various substituents on the o -silyl aryl triflate and the isocyanate. [ABSTRACT FROM AUTHOR]

The scope of an unexpected Mitsunobu cyclisation to prepare N -arylated F sp 3 -enriched azacycles was investigated. In the current study, we have identified whether a p Ka-dependent Mitsunobu cyclodehydration or a p Ka-independent Mitsunobu intra molecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intra molecular nucleophilic displacement was determined to be the dominant pathway. [ABSTRACT FROM AUTHOR]

The one-pot copper/manganese co-catalyzed heterocyclization of arylamine derivatives with styrene and acetone to produce a series of 2-methyl-1,5-diaromatic-1 H -pyrroles was investigated. The described reaction combines 1,4-dicarbonyl synthesis and Paal-Knorr type condensation reactions. [ABSTRACT FROM AUTHOR]

[Display omitted] A visible light-mediated photocatalyst-free N -demethylation of aryl tertiary amines via EDA mechanism is described here. The N -demethylation of the arylamine is effectively enabled by forming an EDA complex of amine and PIDA, giving the corresponding secondary amines in moderate to good yields under irradiation with visible light. Relevant mechanistic experiments have demonstrated the reaction process is mediated by EDA complexes. [ABSTRACT FROM AUTHOR]

[Display omitted] We present a sodium trifluoroacetate (CF 3 CO 2 Na) mediated copper-catalyzed aza -Michael addition of aromatic amines with activated olefins under mild, aqueous reaction conditions. This simplistic protocol employs a copper catalyst (10 mol%) and water as solvent. This transformation occurs precisely with aromatic substituted amines containing both electron-donating (EDG) and electron-withdrawing (EWG) groups. A broad range of substrates were tested under the optimized conditions, which are producing good to moderate yields. [ABSTRACT FROM AUTHOR]

A new macrocyclic AIE emitter composed of triarylamine backbone was successfully synthesized through convenient homocoupling procedure and easily purified by silica gel column chromatography, and recrystallization. The optical and electrochemical properties of the compound have been investigated. Intriguingly, the compound shows dual emission both 423 nm and 505 nm. This result implied that the violet emission was originated from an isolated component of the emitter, whereas the yellowish-green emission simultaneously exhibited AIE nature. The compound exhibits enough thermal stability and high glass transition temperature to be applied for organic devices. [ABSTRACT FROM AUTHOR]

A simple procedure for the synthesis of organo-chalcogenides has been developed by the reaction of aryl/heteroaryl amines with di-aryl/heteroaryl dichalcogenides in the presence of t BuONO and Fe(0) nanoparticles. The reaction proceeds via in situ diazotization followed by chalcogenation. A series of functionalized diaryl/aryl heteroaryl/diheteroaryl/aryl-alkyl selenides, sulfides and tellurides have been obtained by this procedure. Significantly, using this procedure 2,4-dinitroaniline is converted to (2,4-dinitrophenyl)(phenyl)selane which is known as thioredoxin reductase (TR) and glutathione reductase (GR) inhibitor. The reaction goes by a radical pathway and a plausible mechanism has been suggested. [ABSTRACT FROM AUTHOR]

Treatment of N-[(4-hydroxy-6-phenyl)pyrimidin-2-yl]cyanamide with 1° alkyl or arylamines in isopropyl alcohol for only 10 min at 110–120 °C under microwave conditions gave the corresponding N′-alkyl(aryl)guanidine derivatives in excellent yields (65–84%). Isolated yields were greatest when >1.0 equiv. of amines were employed, but excellent results were also obtained when aryl and alkylamines were reacted with a more atom-economical loading (1.0 equiv.; 70% and 72% ave. yields, respectively). Arylamines with either highly electron withdrawing substituents (e.g. CO 2 H) or pi-deficient heterocycles (e.g. variously substituted aminopyridines) did not work well under these conditions, and reaction with ureas and/or amino acids did not give detectable products. Work-up was exceedingly simple, and involved simple collection and washing of product on a sintered glass funnel. Products were obtained in analytically pure form and required approximately 1 h to prepare, start to finish. [ABSTRACT FROM AUTHOR]

A copper-catalyzed, 2,2,6,6-tetramethyl piperidine N-oxy radical-assisted intermolecular diamination of styrenes with N-fluorobenzenesulfonimide has been developed. The current protocol proved amenable to a diverse array of styrenes via cascade radical addition to readily afford synthetically useful aromatic vicinal diamines with exclusive diastereoselectivity. [ABSTRACT FROM AUTHOR]

A novel visible-light (blue LEDs: hν = 425 ± 15 nm) photocatalyzed one-pot method for the synthesis of electronically diverse aryl glyoxals in good to excellent yields from acetoarylones and green regents such as air, vitamin C and dioxane dibromide has been described. In addition, an application of the current methodology has been demonstrated for the oxidation of monoamine oxidase-B inhibitors, i.e., 1-(4-((4-fluorobenzyl)oxy)phenyl)ethanone and 1-(3-((4-chlorobenzyl)oxy)phenyl)ethanone. This finding may serves as a valuable alternative to the traditional acetoarylones oxidation reactions conducted using selenium dioxide a harmful and unselective reagent known to simultaneously oxidize allylic, benzylic, CH 3 and so on. [ABSTRACT FROM AUTHOR]

Described herein is a CoCl 2 –TBHP ( t- butyl hydroperoxide) system that efficiently catalyzes the oxidative annulation of aromatic tertiary amines with a typical electron-deficient alkene, N- substituted maleimides, producing the corresponding polycyclic tetrahydroquinoline derivatives. This oxidizing system could also be applied to the annulation of an electron-rich alkene. [ABSTRACT FROM AUTHOR]

[Display omitted] • The transamidation approaching N -substituted amides from various primary amides and amines was achieved with high yields. • The transamidation was catalyzed by non-harmful PVP-I instead of molecule I 2. • Several drugs were successfully acquired with a better performance than those previous reported references. Non-harmful Povidone iodine (PVP-I) was applied in the transamidation to gain N -substituted amides from various primary amides and amines. Diverse aromatic, heterocyclic and aliphatic primary amides/amines were applied in our developed method and more than 45 N -substituted amides were obtained with excellent yields in most cases. Several drugs such as Melatonin and Efaproxiral were successfully acquired with a better performance than those previous reported results. [ABSTRACT FROM AUTHOR]

[Display omitted] A highly efficient and straightforward synthetic protocol for the synthesis of 2-benzyl-3-arylquinoline derivatives is developed from aryl amines and styrene oxides in the presence of 20 mol% p -toluenesulfonic acids under metal- and solvent-free conditions by employing a pseudo-three-component reaction. Using similar reaction conditions, the synthesis of 2,3-dialkylquinoline derivative can also be accomplished using aliphatic epoxide. The methodology has several advantages such as ease to handle, a broad substrate scope, good yields, metal- and solvent-free reaction conditions, and the formation of one C N and two C C bonds in a single step. [ABSTRACT FROM AUTHOR]

We disclose an efficient molecular I 2 /[bmim]OH-catalyzed activation of carbohydrates as aldehyde equivalent for synthesis of imino/-thiosugar annulated β-lactams in excellent yield (86–94%) and high cis diastereoselectivity (96–99%). The envisaged method involves reaction of unprotected d -glucose/ d -xylose as 1C, masked amino/-mercapto acid as 2C, and aromatic amines as N source in the present three-component synthesis. The reaction is effected via intramolecular aza-Michael addition followed by amino/-mercaptoacetylative cyclization in a one-pot procedure. The developed methodology for β-lactam synthesis has advantage of its operational simplicity, ambient reaction conditions, and the ionic liquid, [bmim]OH could be easily recycled for further use without any loss of efficiency. [ABSTRACT FROM AUTHOR]

A convenient and efficient metal free borylation of aromatic amines has been achieved using tertiary butyl nitrite and B 2 Pin 2 (bis(pinacolato)diborane) under irradiation with blue LED light at room temperature. This protocol has been successfully extended to subsequent Suzuki coupling in the same pot. Thus a series of functionalized aryl boronates and biaryls are obtained in high yields in a shorter reaction period starting from relatively cheap aryl amines in one-pot avoiding isolation of potentially unstable and hazardous intermediates. [ABSTRACT FROM AUTHOR]

Boron trifluoride monohydrate is an excellent Brønsted acid catalyst system for a wide range of reactions. It is a non-oxidizing acid catalyst prepared easily by bubbling BF 3 into water. We have found boron trifluoride monohydrate/sodium azide combination to be an efficient reagent system for aromatic electrophilic amination. The present method avoids the use of expensive superacids such as trifluoromethanesulfonic acid and provides a facile access to aromatic amines directly from aromatics. [ABSTRACT FROM AUTHOR]

A silver-catalyzed formation of C–C bond for the construction of a series of polysubstituted quinolines from arylamines, aldehydes, and ketones or arylamines and 1,3-diketones has been developed. The transformation is effective for a broad range of substrates, thus enabling the expansion of constituent architectures on the heterocyclic framework. This use of a single catalytic system to mediate chemical transformations in a synthetic operation is important for the development of new atom-economic strategies and this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion. [ABSTRACT FROM AUTHOR]

A series of novel pyrrolo[3,4- b ]quinolines have been synthesized from N -alkynyl aldehydes and various substituted arylamines in good to excellent yields utilizing an intramolecular Povarov reaction catalyzed by boron trifluoride diethyl etherate as the key final step. [ABSTRACT FROM AUTHOR]

The CuSO 4 /ascorbate-mediated ‘click’ reaction of 2-(2-azidophenyl)-4,5-diaryloxazoles and arylacetylenes proceeded through an alternate pathway whereby reduction of the azide predominated over formation of the 1,2,3-triazole-forming cycloaddition. The unimolecular product, 2-(2-aminophenyl)-4,5-diphenyloxazole, was isolated which appears to be a formal reduction of the arylazide to the corresponding arylamine. A series of oxazoles which possessed various substituents (F, Cl, Br, OCH 3 ) on the 4,5-diaryl rings and having the 2-azido group on the 2-oxazolylphenyl position were submitted to the same ‘click’ conditions and gave the corresponding arylamine products (73–99%). The reaction appears to be specific toward the ortho -azido substitution of the polycyclic system, as the corresponding azidomethyl-substituted phenyl oxazoles do not give the ‘reduction’ products but gave the expected click products with the acetylenic co-reactants. [ABSTRACT FROM AUTHOR]

[Display omitted] An efficient, rapid and green synthesis of indolo-furo-quinoline and chromeno-furo-indoles has been developed by one-pot reaction of 2,4-quinolinediol or 4-hydroxycoumarin, phenylglyoxal and aromatic amine in the presence of acetic acid as an reaction medium cum promoter at room temperature. This scalable tandem reaction affords a series of novel dihydro-indolo-furo-quinoline and dihydro-chromeno-furo-indole derivatives with two adjacent stereogenic centers in good to excellent yields and with high regioselectivity and stereoselectivity. Moreover, this cascade reaction provides a distinct Knoevenagel, Michael and through intramolecular cyclization in sequential manner under mild reaction conditions to access the diversely decorated indolo-furo-quinoline and chromeno-furo-indoles of considerable importance to natural product synthesis and medicinal chemistry. [ABSTRACT FROM AUTHOR]

Excellent catalytic stereoselectivity (up to > 99:1) with good yields (up to 88%) for Mannich reaction process under the solvent-free conditions at room temperature has been developed. [Display omitted] A series of indole-based organocatalysts (4b,9b-aryl-4b,5,9b,10-tetrahydroindolo[3,2- b ]indole derivatives) (2a-2f) have been designed and synthesized for the three-component direct Mannich reaction of aromatic aldehydes and aromatic amines with ketones. Significantly, the organocatalyst 2a delivered excellent catalytic stereoselectivity (up to >99:1) with good yields (up to 88 %) for above reaction process under the solvent-free conditions at room temperature. X-ray diffraction analysis reveals that organocatalyst 2a is of eight-membered central ring structure with interesting strained quadricyclic ring connectivity. The characteristic rigid V-shape indole ring structure contained in 2a and the formed hydrogen-bonding interaction between 2a and intermediate prefer to the anti-stereoselective product. [ABSTRACT FROM AUTHOR]

A rapid and efficient single-step synthesis of substituted anilines has been developed. The aromatic nitro compounds were reduced by using reducing systems generated by the action of an excess of LiAlH 4 on TiCl 4 . Anilines substituted with different functional groups were synthesized in high yields and purity starting from the corresponding nitro compounds. The developed procedure is applicable to nitroaromatics containing both electron withdrawing and electron donating substituents. Substrates with electron donor substituents require a larger excess of LiAlH 4 . The reducing power of the prepared reactant systems depends on the used molar ratio of LiAlH 4 and TiCl 4 . [ABSTRACT FROM AUTHOR]

A transamidation reaction of thioacetamide with primary and secondary amines is described. The use of catalytic amounts of SbCl 3 notably increases the yields and diminishes the reaction times. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. This is one of the few examples where antimony has been used as a catalyst in organic reactions. [ABSTRACT FROM AUTHOR]

A simple and convenient N-devinylation and N-deallylation strategy for N -vinyl and N -allyl arylamines in the presence of TFA/oxone is presented with the formation of selective ortho -hydroxylated and N -trifluoroacylated arylamine product in good yields. This method is important for protection/deprotection of arylamines in organic synthesis and useful as a medicinal chemistry tool at late stage modifications in drug discovery programs. [ABSTRACT FROM AUTHOR]

A practical and efficient strategy has been described for the preparation of 4-quinolone derivatives. Using commercially available diethyl acetylenedicarboxylate and aromatic amines as starting materials, the synthetic protocol has been achieved and afforded the product via hydroamination at room temperature followed by PPA-catalyzed intramolecular ring closure. The products can be easily obtained in high yields. Conditions and mechanism of the reaction have also been investigated. This protocol is environmentally friendly and transition-metal-free, with advantages including short reaction time, convenient operation, and mild reaction conditions. [ABSTRACT FROM AUTHOR]

A concise and efficient synthetic approach was developed for the synthesis of functionalized chromeno[4,3- b ]pyrrol-4(1 H )-ones via a one-pot, three-component reaction of 4-aminocoumarin, arylglyoxal monohydrates, and aromatic amines promoted by KHSO 4 in toluene under reflux condition. The attractive features of this protocol are operational simplicity, short reaction time, easy purification of products and good to excellent yields. [ABSTRACT FROM AUTHOR]

A mild and efficient synthesis of 3,3-disubstituted oxindoles is achieved. The corresponding diazonium salts are generated in situ from aromatic amines before these salts undergo a homolytic bond cleavage to produce the aryl radicals. Various oxindoles are obtained by homolytic aromatic substitution and radical cyclization. This procedure is an alternative method to oxindole synthesis. [ABSTRACT FROM AUTHOR]

Using palladium(II)-catalyzed intramolecular C–H activation/C–C cross coupling we synthesized three natural carbazoles (clauraila A, clausenal, and 6-methoxymurrayanine) from formyldiarylamines. The versatile strategy used here allowed us to obtain these alkaloids with fewer synthetic steps and in similar overall yields to methods previously reported. We present the first use of Pd(acac) 2 as a catalyst for this cyclodehydrogenation, which is a novelty that reveals mechanistic details about the reaction. [ABSTRACT FROM AUTHOR]

Convenient and environmentally benign methods for the syntheses of α-amino ketones and pentasubstituted pyrrole derivatives are reported. Initially, α-amino ketones are prepared from the reaction of benzoin derivatives and aromatic amines using a catalytic amount of silica tungstic acid. Next, the α-amino ketones synthesized are reacted with dimethyl acetylenedicarboxylate in the presence of silica sodium carbonate as a new solid basic catalyst to form the corresponding pyrrole derivatives. [ABSTRACT FROM AUTHOR]

[Display omitted] This article reports an efficient method for the synthesis of amide derivatives by the direct reactions of aromatic amines with 1,3-diketones promoted by pyridine hydrochloride under metal-free and solvent-free conditions. This transformation was accomplished by cleavage of C C bond in the presence of pyridine hydrochloride as additive, which excludes the use of transition-metals and harsh reaction conditions. This method has a broad substrate scope and good tolerance for sensitive functional groups. A multi-gram scale reaction is also performed to ensure the scalability of the reaction. [ABSTRACT FROM AUTHOR]

A PhI(OAc) 2 -mediated four-component tandem annulation with basic modules of amine, aldehyde, alkyne and halide salt for concise and efficient synthesis of functionalized 3-haloquinolines has been established. This strategy merging A3-coupling and redox reaction of halide salt, namely A3-X type tandem reaction, is step economic, functional groups flexible, and potentially applicable to complex molecules. [Display omitted] Utilizing simple precursors for the exquisite construction of molecules with diversity and complexity is urgent. Herein, a novel A3-X type reaction for functionalized 3-haloquinolines has been developed by PhI(OAc) 2 -mediated four-component tandem addition/cyclization/oxidation/aromatization process with simple aromatic amine, aldehyde, alkyne and halide salt. Broad functional group tolerance, very mild condition, easy for further transformation illustrate the concision, high efficiency and practicability of this A3-X type reaction. [ABSTRACT FROM AUTHOR]

An efficient and general selective method for the synthesis of 8-aminoquinoline derivatives has been disclosed through transition metal direct C–N coupling from fluoroquinolines and arylamines. Significantly, good chemo- and regio-selectivity was observed for polyfluoroquinolines in which only C–F bond on 8-substituted position was broken. Thus, this methodology proves its value as an inexpensive and efficient synthetic way to access quinolin-8amine derivatives in moderate to good yields. [ABSTRACT FROM AUTHOR]

Aryl amines undergo smooth annulation with O -phenylpropynyl sugar aldehyde in the presence of the Ph 3 PAuCl (10 mol %)/AgSbF 6 (10 mol %) catalytic system to afford the corresponding tetrahydro-3a H -spiro[[1,3]dioxolo[4″,5″:4′,5′]furo[3′,2′:5,6]pyrano[4,3- b ]quinoline-2,1′-cyclohexane] derivatives in good yields and selectivity. [ABSTRACT FROM AUTHOR]

An efficient one-pot synthesis of N α -protected S-linked 1,3,5-triazine tethered peptidomimetics is described. The protocol involves a three-component condensation reaction employing N α -protected amino alkyl isothiouronium salt, formaldehyde and amino acid ester or aryl amine as reactants. Various aryl amines with substitutions and amino acids with simple as well as bifunctional side chains were employed to obtain triazine tethered peptidomimetics in good yield. [ABSTRACT FROM AUTHOR]