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The document is the contents list for an issue of the journal Chemical Communications. It includes the titles and authors of various articles and features that will be included in the issue. The articles cover a range of topics in the field of chemistry, including recent advances in biosensing systems, continuous flow synthesis, electrochemical construction, and more. The journal is published by The Royal Society of Chemistry, a leading chemistry community. [Extracted from the article]

An efficient palladium-catalyzed cascade cyclization/carbonylation of indoles with aryl formates to access ester-functionalized indolo[2,1-a]isoquinoline scaffolds has been developed. In addition, an asymmetric variant is also achieved using a chiral phosphine ligand, affording the indolo[2,1-a]isoquinoline products in good yields and enantioselectivities. [ABSTRACT FROM AUTHOR]

Chemical Communications is a journal published by The Royal Society of Chemistry, which is a leading chemistry community. The journal features articles on various topics in the chemical sciences. The current issue includes a highlight on the cover, as well as feature articles on topics such as the inhibition of fibril formation by polyphenols and recent advances in circularly polarized luminescence. The journal also provides information on approved training courses offered by The Royal Society of Chemistry. [Extracted from the article]

The document is a contents list for the journal "Chemical Communications" published in 2024. It includes a variety of articles on topics such as cell-free synthetic biology, metal-organic framework-based materials for cancer therapy, and the formation of iminium ions in metal halide perovskites. The journal is published by The Royal Society of Chemistry, a leading chemistry community. The document provides a glimpse into the research and discoveries in the field of chemistry. [Extracted from the article]

In this study, a Rh(III)-catalyzed C–H/N–H [4+2] annulation of oxadiazolones with iodonium ylides has been developed, which afforded a series of diverse fused-isoquinolines and fused-pyridines in moderate to high yields. These divergent synthesis protocols featured mild conditions, broad substrate scope, and functional-group compatibility. In addition, scale-up synthesis, related applications and preliminary mechanistic explorations were also accomplished. [ABSTRACT FROM AUTHOR]

Co(III)-catalysed site-selective C8-allylation and vinylation of isoquinolones with allyl acetate and vinyl acetates has been accomplished. The oxo group of isoquinolone has been utilised as an inherent directing group. Based on preliminary mechanistic studies, a plausible mechanism for the developed reaction has also been delineated. Broad substrate scope with good to excellent yields and post-synthetic transformations of allylated and vinylated isoquinolines highlight the importance of the reaction. [ABSTRACT FROM AUTHOR]

A pyrrolo[2,1-a]isoquinoline core structure is prevalent in marine and other natural products. This article describes a tungsten-catalyzed [3+2] cycloaddition aromatization of dihydroisoquinoline ester and maleic anhydride or an acrylate. The photochemical reaction tolerates a range of functional groups such as ester, cyano, ketone, bromide, and alkene. It is shown that the cycloaddition-aromatization of 2-substitued acrylate catalyzed by a tungsten photocatalyst can be used to evaluate the leaving ability of the leaving group. Experiments done to determine the reaction mechanism revealed that the formation of an ion-pair intermediate generated in situ from dihydroisoquinoline ester and (Z)-4-methoxy-4-oxobut-2-enoic acid via the solvolysis of maleic anhydride with methanol is crucial for the cascade process to occur. The key cycloadduct acid intermediate derived from [3+2] cycloaddition was isolated and determined by X-ray crystallography. [ABSTRACT FROM AUTHOR]

A coordination polymer, [Cu(SCN)(iqi)]n (iqi = isoquinoline), containing copper(I) thiocyanate and a nitrogen-containing π-conjugated ligand, iqi, has been synthesized and its physical properties were evaluated. This coordination polymer has a two-dimensional (2D) sheet structure consisting of copper(I) thiocyanate and shows photoluminescence derived from 3MLCT and photoconductive properties. [ABSTRACT FROM AUTHOR]

We herein report regio- and enantioselective arylation of β,γ-alkynyl-α-imino esters with pyrroloisoquinolines. Using chiral phosphoric acid catalysts, a wide range of novel axially chiral tetrasubstituted α-amino allenoates were accessed in good yields with excellent enantioselectivities. Notably, this transformation occurred preferentially at the sterically more hindered C1-position of pyrroloisoquinolines. The potential scalability and late-stage functionalization demonstrated the utility of the current protocol. [ABSTRACT FROM AUTHOR]

Both chromenone and pyrrolo[2,1-a]isoquinolines (containing ring-junction nitrogen) are privileged scaffolds in the field of synthetic as well as medicinal chemistry. These fused hybrid moieties are found to be present in diverse natural products like lamellarins and in many biomaterials. Here, we summarize some synthetic methodologies in connection with the synthesis of 2- and 4-chromenones fused to the five-membered ring of pyrrolo[2,1-a]isoquinolines in diverse orientations and their biological significance as reported in the relevant research articles. Several methods for the synthesis of various such fused compounds have been reported in the literature by way of construction of either pyrrole, pyridine, isoquinoline, coumarin (2H-chromen-2-one), 4H-chromen-4-one or more rings simultaneously by the use of eco-friendly classical methods or transition metal-catalyzed methods. [ABSTRACT FROM AUTHOR]

Eighteen mononuclear copper(II) complexes with oxygen-containing N4O1 pentadentate ligands were prepared. The ligand library consists of 2-aminoethanol derivatives ((Ar1CH2)(Ar2CH2)NCH2CH2OCH2Ar3) bearing three nitrogen-containing heteroaromatics (Ars) including pyridine, quinoline and isoquinoline via a methylene linker. Systematic replacements of pyridine binding sites with quinolines and isoquinolines reveal the general trends in the perturbation of bond distances and angles, the redox potential and the absorption maximum wavelength of the copper(II) complexes, depending on the position and number of (iso)quinoline heteroaromatics. The small effect on the redox potentials resulting from quinoline substitution at the Ar3 position (near oxygen) of the ligand comes from the steric hindrance of the peri hydrogen atom in the quinoline moiety at this position, which removes the counter anion to enhance the coordination of quinoline nitrogen and ether oxygen atoms to the metal centre. In the absorption spectra of copper(II) complexes in the d–d transition region, the quinoline substitution at this site (Ar3) exhibits an opposite effect to those at the Ar1 and Ar2 sites. The electronic and steric contributions of the heteroaromatic binding sites to the ligand properties are comprehensively discussed. [ABSTRACT FROM AUTHOR]

A pair of high-efficiency deep-red emissive ionic iridophosphors (Ira and Irb) showing high photoluminescence quantum yields (PLQYs) are rationally designed by using 1-(thiophen-2-yl)isoquinoline as the cyclometalating ligand. Two bulky tetraarylborate anions (tetraphenylborate and tetrakis(3,5-bis(trifluoromethyl)phenyl)borate) are selected to improve their PLQYs in both solution and aggregated states, which enables efficient electroluminescence via a solution-processed approach. The variation of the tetraarylborate anions also aims to tune the photophysical properties of these deep-red emissive iridophosphors. Both ionic iridophosphors emit intense deep-red room-temperature phosphorescence in both solution and aggregated states. The phosphorescence spectra of both complexes are similar (630 nm with a shoulder emission of 686 nm) in CH2Cl2, originating from the same cationic species of the complexes. Both complexes show high PLQYs in CH2Cl2 (0.41 for Ira, 0.43 for Irb) and neat films (0.27 for Ira, 0.34 for Irb). Moreover, they serve as triplet emitters to evaluate their performance in solution-processed deep-red electroluminescent devices. The maximum external quantum efficiencies for the deep-red electroluminescence are 7.3% with an emission maximum of 649 nm for Ira, and 10.2% with an emission maximum of 635 nm for Irb, respectively, implying that they are good candidates for high-performance electroluminescence. [ABSTRACT FROM AUTHOR]

Visible-light-induced C–C bond breakage of cyclobutanone oxime esters reacted with 2-aryl indole derivatives to afford a variety of cyanoalkyl indolo[2,1-a]isoquinolinones in high yields was developed. The organophotocatalytic radical cascade cyclization reaction uses an inexpensive photosensitizer without any additives in a simple and scalable set-up, and allows the inclusion of many other functional groups. [ABSTRACT FROM AUTHOR]

A facile [3+3] annulation method for the construction of fused α-carboline or indolo[2,3-c]isoquinoline frameworks from easily synthesizable N,N′-cyclic azomethine ylides and 3-diazoindolin-2-imines using a Ru(II) catalyst is reported. This strategy was found to be efficient and effective for the syntheses of a variety of fused polycyclic molecules with a wide substrate scope, mild reaction conditions, and good to excellent yields. In addition, the mechanistic pathway of this transformation has been investigated by performing various control experiments with ESI-MS analyses. [ABSTRACT FROM AUTHOR]

A Cu(I)-promoted exclusive synthesis of pyrrolo[2,1-a]isoquinoline derivatives involving (E)-2-methoxyethene-1-sulfonyl fluoride (MESF) and isoquinolinium N-ylides is described. MESF was used as an acetylene substitute for [3+2] cycloaddition and a variety of C1/C2 non-functionalized pyrrolo[2,1-a]isoquinoline derivatives were prepared. [ABSTRACT FROM AUTHOR]

Optically-pure triptycene-based metallomacrocycles are, for the first time, synthesized by the coordination-driven self-assembly of enantiopure triptycene-derived ladder-type bis(benzo[f]isoquinoline) ligands with a cis-platinum(II) complex. A pair of enantiomeric homochiral metallomacrocycles is also produced by the coordination-driven homochiral self-sorting of the corresponding racemic ligands, which relies on the shape-persistent nature of the ladder-structured ligands. [ABSTRACT FROM AUTHOR]

Dearomatization reactions provide a rapid approach to construct complicated molecules that are difficult to synthesize by traditional methods from simple aromatic compounds. Herein, we report an efficient dearomative [3+2] cycloaddition reaction of 2-alkynyl pyridines with diarylcyclopropenones, leading to the synthesis of densely functionalized indolizinones in moderate to good yields under metal-free conditions. In addition, this strategy can also be employed in dearomative cyclization of isoquinolines to access a variety of benzo-fused indolizinones. Density functional theory (DFT) calculations revealed that an appropriate substituent at the 2-position of pyridine is crucial to the dearomatization process. [ABSTRACT FROM AUTHOR]

Herein, we report a metal/additive-free protocol for the activation of nitrile towards nucleophilic addition and subsequent annulation under an aqueous medium for the first time. The protocol divulges an efficient and atom economical route for the construction of diverse aminated isoquinolines. Differently substituted primary as well as secondary amines underwent the reaction in a highly regioselective manner. The reaction is operationally simple, shows high functional group tolerance and easier modification of well-known drugs, and can be successfully extended to gram-scale synthesis. [ABSTRACT FROM AUTHOR]

This manuscript reports the synthesis, X-ray characterization and DFT study of a series of all-cis 3a,6 : 4,5 : 7,9a-triepoxy and 3a,6 : 7,9a-diepoxybenzo[de]isoquinolines obtained by the tandem intramolecular [4 + 2]/[4 + 2] cycloaddition in bis-furans (the IMDAF reaction) between difurfurylamine derivatives and dimethyl acetylenedicarboxylate (DMAD) as a dienophile. In one compound instead of DMAD, 1-phenyl-1H-pyrrole-2,5-dione (N-phenylmaleimide) was used as a dienophile. The existence of a "through-space" alpha-effect is analyzed in these compounds, since in three of them N–H⋯O2 H-bonds are observed in the solid state promoting the formation of self-assembled dimers. That is, the close O⋯O distance between the O-bridge atoms due to the rigidity of these molecules causes a lone pair⋯lone pair (LP⋯LP) interaction that enhances the H-bond acceptor ability of the bridging atoms (through-space α-effect). This fact has been studied using DFT calculations, molecular electrostatic potential (MEP) surfaces, electron localization function (ELF), quantum theory of atoms-in-molecules (QTAIM) and noncovalent interaction plot (NCIplot) index computational tools. This is the third study of the literature where "α-effect" hydrogen bonds (AEHBs) are described. The novelty of the present work resides in the utilization of an amine linker between the furan rings that allows the incorporation of a good H-bond donor in the model system. As a result, NH⋯O2 instead of CH⋯O2 AEHBs described in previous works are established. The X-ray analyses of the synthesized di- and tri-epoxides reveal that the AEHBs are predominant in the X-ray architecture of these compounds. [ABSTRACT FROM AUTHOR]

An efficient and enantioselective phosphonation protocol for construction of chiral α-aminophosphates and α-aminodiarylphosphine oxides has been developed based on chiral phosphoric acid-catalyzed dearomatization of isoquinolines. A series of chiral 1,2-dihydroisoquinolines with dimethoxy phosphoryl or diphenylphosphono substituents at the C1-position were constructed with good to excellent yields and enantioselectivities under mild reaction conditions. [ABSTRACT FROM AUTHOR]

A novel and efficient catalyst-free and oxidant-free tandem aza-Mannich/cyclization/aromatization reaction of C,N-cyclic azomethine imines with enamides has been developed. This practical one-step protocol enables a simple and environmentally friendly route toward the straightforward synthesis of highly substituted 5,6-dihydropyrazolo[5,1-a]isoquinolines. Different types of enamides and enamines, especially enamides derived from marketed drugs as well as bioactive molecules, are suitable substrates. CB1 cannabinoid receptor antagonist could be synthesized efficiently based on this methodology, illustrating that this would be a practical strategy to synthesize valuable structural motifs. [ABSTRACT FROM AUTHOR]

Highly selective and switchable [4+2] annulations of 2-arylindoles with iodonium ylides were achieved by performing solvent-controlled Rh(III)-catalyzed C–H activations. When using DCM as a solvent, the C–H functionalization of 2-arylindoles with iodonium ylides selectively delivered indolo[2,1-a]isoquinoline derivatives. In contrast, the same catalytic system with a polar HFIP solvent predominately provided benzo[a]carbazole moieties. [ABSTRACT FROM AUTHOR]

Under transition metal catalyst-free conditions, we herein present a hydride transfer-initiated construction of novel 3-(2-aminomethyl)aryl quinolines from N-isoquinolinium salts and 2-aminobenzaldehydes, proceeding with the merits of operational simplicity, high step and atom efficiency, good substrate and functional group compatibility, and mild conditions. The products are formed by reacting with the isoquinolyl motif as a two-carbon synthon along with the cleavage of its C3–N bond. Given the interesting applications of 3-aryl quinolines, the developed chemistry is anticipated to be further applied to develop new functional products. [ABSTRACT FROM AUTHOR]

The reaction of dithiooxamide with aromatic aldehydes is a well-known method for the preparation of thiazolo[5,4-d]thiazoles (TzTz). However, we report here that, using adequately substituted 2-halobenzaldehydes, this reaction may afford selectively thiazolo[5,4-c]isoquinolines (TzIQ) or mixtures of TzTz and TzIQ. The use of lanthanum(III) triflate as the catalyst favors the formation of TzIQ. The results obtained using a large number of substituted benzaldehydes showed that the nature, number and position of halogen atoms and other substituents on the aldehyde have a great impact on the reaction outcome. The structures of six TzTz and six TzIQ were unveiled by single-crystal X-ray diffraction. [ABSTRACT FROM AUTHOR]

This new investigation describes an efficient three-component approach for the stereoselective synthesis of pyrrolo[2,1-a]isoquinolines from readily available isatins, chalcones and 1,2,3,4-tetrahydroisoquinoline without using a metal catalyst or additive. The synthetic methodology was found to be equally successful with differently functionalised secondary amines. A series of pyrrolo[2,1-a]isoquinolines were synthesised in good yields (up to 87%), and a single diastereomer product was formed exclusively in all the cases. The comprehensive analysis of the interaction between the ligand and the receptor obtained from in silico molecular docking on the active sites of ACP reductase (4OHU) indicates that our synthesised compounds have better anti-tuberculosis properties than the standard drug Rifampicin. [ABSTRACT FROM AUTHOR]

Covering: 2015 to 2020 Nitrogen heterocyclic natural products (NHNPs) are primary or secondary metabolites containing nitrogen heterocyclic (N-heterocyclic) skeletons. Due to the existence of the N-heterocyclic structure, NHNPs exhibit various bioactivities such as anticancer and antibacterial, which makes them widely used in medicines, pesticides, and food additives. However, the low content of these NHNPs in native organisms severely restricts their commercial application. Although a variety of NHNPs have been produced through extraction or chemical synthesis strategies, these methods suffer from several problems. The development of biotechnology provides new options for the production of NHNPs. This review introduces the recent progress of two strategies for the biosynthesis of NHNPs: enzymatic biosynthesis and microbial cell factory. In the enzymatic biosynthesis part, the recent progress in the mining of enzymes that synthesize N-heterocyclic skeletons (e.g., pyrrole, piperidine, diketopiperazine, and isoquinoline), the engineering of tailoring enzymes, and enzyme cascades constructed to synthesize NHNPs are discussed. In the microbial cell factory part, with tropane alkaloids (TAs) and tetrahydroisoquinoline (THIQ) alkaloids as the representative compounds, the strategies of unraveling unknown natural biosynthesis pathways of NHNPs in plants are summarized, and various metabolic engineering strategies to enhance their production in microbes are introduced. Ultimately, future perspectives for accelerating the biosynthesis of NHNPs are discussed. [ABSTRACT FROM AUTHOR]

Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. [ABSTRACT FROM AUTHOR]

A K2S2O8-catalyzed versatile C(sp2)–C(sp3) bond formation with N-heteroaromatics and γ-lactams/amides was developed. Quinoxalin-2(1H)-one, quinoline, isoquinoline, phthalazine, and benzothiazole reacted with γ-lactams/amides to give the corresponding C(sp2)–H amidoalkylation products in moderate to good yields with high regioselectivity. This visible-light-induced photocatalyst-free reaction was conducted in H2O at ambient temperature, which comply with the principles of "green chemistry". The new K2S2O8 catalytic mechanism was investigated with control experiments. [ABSTRACT FROM AUTHOR]

The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance. [ABSTRACT FROM AUTHOR]

An efficient sulfuration of isoquinolin-1(2H)-ones at the C-4 position is reported by employing ethyl sulfinates, and the corresponding products are obtained in moderate to excellent yields in the presence of iodine. This synthetic strategy provides a range of thioether-isoquinolin-1(2H)-ones while tolerating a number of functional groups on the isoquinoline nitrogen atom and benzene ring. In addition, pyridin-2(1H)-one is also reacted smoothly and afforded the corresponding thioether product in moderate yield. A plausible mechanism is suggested based on the preliminary mechanistic studies. [ABSTRACT FROM AUTHOR]

Rational molecular structure alterations of TQEN (N,N,N′,N′-tetrakis(2-quinolylmethyl)ethylenediamine) produced variable fluorescent sensors for specific metal ions and phosphate species. Utilization of methoxy-substituted quinoline and isoquinoline chromophores, conformational restriction and multidentate coordination structure allow discrimination between Zn2+ and Cd2+. Pyrophosphate (P2O74−, PPi) and phosphate (PO43−) also are selectively detected with dinuclear Zn2+ complexes of tetrakisquinoline-based ligands. Differential stability and structure of the metal complexes, as well as resulting fluorescence enhancement mechanism, such as intramolecular excimer formation via change in coordination geometry, play key roles in the discrimination of target ions. [ABSTRACT FROM AUTHOR]

The synthesis, X-ray characterization and Hirshfeld surface analysis of a series of tetrahydro-diepoxybenzo[de]isoquinoline derivatives obtained by the tandem [4+2] cycloaddition between perfluorobut-2-yne dienophile (F3C–C≡C–CF3) and a row of N,N-bis(furan-2-ylmethyl)-4-R-benzenesulfonamides (bis-dienes, R = Me, F, Cl, Br, I) are reported in this manuscript. The implementation of kinetic/thermodynamic control allowed us to obtain both "pincer"- and "domino"-type adducts in good/moderate yields. In the solid state, most of the pincer adducts form self-assembled dimers (R = Me, Cl, Br, I) and, contrariwise, the domino adducts form 1D supramolecular chains, which are described in detail herein. Remarkably, in the self-assembled dimers, bifurcated halogen bonds involving one fluorine atom of the CF3 group and both O-atoms of sulfonamide are formed, which have been analyzed using DFT calculations, and the QTAIM and NCIplot computational tools. [ABSTRACT FROM AUTHOR]

Two new bifunctional isolated hybrid compounds, [ε-PMo V8 Mo VI4 O37(OH)3Zn4][iql]4·6H2O (1) and [ε-PMo V8 Mo VI4 O38(OH)2Zn4][bipy]3[(CH3COO)(bipy)2Zn]·2H2O (2) (where iql = isoquinoline and bipy = 2,2′-bipyridine), based on Zn-ε-Keggin were successfully synthesized by self-assembly under hydrothermal conditions. It is interesting to note that acetate in 2 acted as a linker connecting the ε-Keggin anion with the one Zn atom (Zn5) and enabled the ε-Keggin anion to coordinate with more bipy ligands, culminating with a larger isolated system, which is the first reported isolated cluster of Zn5PMo12. Meanwhile, compounds 1–2 show great electrochemical behaviors and excellent electrocatalytic activity for the degradation of NaNO2. In addition, compound 2 displays better third-order NLO performance than 1 due to the presence of more conjugated rings, with a TPA cross section (σ) of 1819 GM, which suggests that compound 2 has the potential to function as a bifunctional material with tremendous prospects. [ABSTRACT FROM AUTHOR]

Signal amplification by reversible exchange (SABRE), a parahydrogen-based hyperpolarization technique, is valuable in detecting low concentrations of chemical compounds, which facilitates the understanding of their functions at the molecular level as well as their applicability in nuclear magnetic resonance (NMR) and magnetic resonance imaging (MRI). SABRE of 1-aminoisoquinoline (1-AIQ) is significant because isoquinoline derivatives are the fundamental structures in compounds with notable biological activity and are basic organic building blocks. Through this study, we explain how SABRE is applied to hyperpolarize 1-AIQ for diverse solvent systems such as deuterated and non-deuterated solvents. We observed the amplification of individual protons of 1-AIQ at various magnetic fields. Further, we describe the polarization transfer mechanism of 1-AIQ compared to pyridine using density functional theory (DFT) calculations. This hyperpolarization technique, including the polarization transfer mechanism investigation on 1-AIQ, will provide a firm basis for the future application of the hyperpolarization study on various bio-friendly materials. [ABSTRACT FROM AUTHOR]

Three new 1D chain structure type hybrid organic–inorganic lead(II) halides are presented: IQPbBr3, QPbBr3 and QPbI3, templated by large organic cations, isoquinolinium ([IQ+] = protonated isoquinoline) and its isomer quinolonium ([Q+] = protonated quinoline). All three compounds possess the same generic formula as cubic perovskite, ABX3, but adopt different structures. IQPbBr3 adopts a 1D face-sharing single chain hexagonal perovskite structure type, and the other two, QPbBr3 and QPbI3, adopt a non-perovskite structure which is built from 1D edge-sharing octahedral double chains. Crystal structures and preliminary photophysical properties are discussed. Two of them have lower bandgaps than the other reported materials with the same structure type, indicating the value of further exploratory studies for these types of materials. [ABSTRACT FROM AUTHOR]

An efficient asymmetric acyl-Mannich reaction of isoquinolines with α-(diazomethyl)phosphonate and diazoacetate has been developed using chiral spiro phosphoric acids as catalysts. This reaction allowed the construction of a series of chiral 1,2-dihydroisoquinolines bearing a tertiary stereocenter at the C1 position with up to 98% yield and 99% ee. [ABSTRACT FROM AUTHOR]

An effective and regioselective strategy for trifluoromethylation and perfluoroalkylation of isoquinolines and heteroarenes was developed. By combination of TMSCnF2n+1 (n = 1, 2, 3) with PIFA, the method achieved the corresponding perfluoroalkylated products with broad functional group tolerance. [ABSTRACT FROM AUTHOR]

For the first time, a new magnetic separation strategy for alkaloids from Coptis chinensis was developed in this study. For basic research, physical properties including thermal properties, solubility and magnetic properties of six Fe-containing magnetic compounds based on isoquinoline alkaloids (including isoquinoline, berberine, palmatine, tetrahydropalmatine, tetrahydropapaverine and berbamine) were characterized firstly, which showed good thermal stability (Tstart > 190 °C) and expected magnetic susceptibility (>1.35 × 10−5 emu g−1). The Gouy method measurement results were in agreement with the order determined using a vibrating sample magnetometer. Then the new integrated method of extraction–derivatization–magnetic separation was successfully applied for the target isoquinoline compounds from Coptis chinensis for the first time on the basis of the above studies, and the recovery of various samples was in the range of 96.85–101.4%. As the key operation in the whole process, derivatization/magnetization not only makes these alkaloids exhibit a good magnetic response in various states but also provides a new strategy of magnetic separation after their extraction. As a result, the effects of different extraction and derivatization conditions were investigated for target compounds from Coptis chinensis in detail. [ABSTRACT FROM AUTHOR]

A novel method for the synthesis of 3-(2-quinolyl) chromones through a tandem [3+2] cycloaddition/ring-opening/O-arylation from ynones and quinoline N-oxides has been developed. This protocol proceeds under transition metal- and additive-free conditions and can be amplified to the gram level in 91% yield. 3-(1-Isoquinolyl) and 3-(2-pyridyl) chromones are also successfully synthesized using isoquinoline and pyridine N-oxides under basic conditions. Various heteroarene-contaning chromones were afforded in 30–98% yields, which are difficult to be obtained and are compounds of interest in pharmaceutical chemistry and chemical biology. [ABSTRACT FROM AUTHOR]

A formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides via visible light-driven photoredox catalysis is reported. Under transition metal-free conditions using a dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst, the transformation was efficient and led to a series of important diazabicyclo[3.2.1]octane-based N-heterocyclic compounds. This work demonstrates the synthetic utility of N-aryl α-amino acids as 1,2-synthons and provides a new strategy for the dearomatization of isoquinolines. [ABSTRACT FROM AUTHOR]

An unprecedented sequential [3+3]/[3+3] annulation of allenoates and dienes catalyzed by phosphine has been developed, which provides novel and facile access to highly functionalized hydroisoquinoline derivatives. The reaction features a wide reaction scope and mild reaction conditions. δ-sulfonamido-allenoates, acting as a five-atom unit, represent a new synthon in the reactions of allenoates. [ABSTRACT FROM AUTHOR]

Two rhodium complexes Rh1 and Rh2 with isoquinoline derivatives were synthesized and characterized. Both complexes displayed strong anticancer activity against various cancer cells and low cytotoxicity against non-cancer cells. These complexes triggered apoptosis via mitochondrial dysfunction that increased the levels of ROS and Ca2+ and released cytochrome C which ultimately activated caspases and the apoptosis pathway. The different biological activities of Rh1 and Rh2 could be associated with the presence of methoxy substituents on the ligands. In vivo studies showed that Rh1 effectively inhibited tumor growth in a T-24 xenograft mouse model with a less adverse effect than cisplatin. Overall, Rh1 and Rh2 induced apoptosis via mitochondrial pathways and could be developed as effective anticancer agents. [ABSTRACT FROM AUTHOR]

An efficient and base-mediated one-pot regiospecific synthesis of structurally diversified isoquinolines and benzo[h] isoquinolines from easily accessible ortho-formyl-arylketones and aryl/(het)arylmethanamines has been described. Challenging 3-alkynyl/alkenyl isoquinolines and bis-isoquinolines were easily attained through this developed chemistry, which can be further used for various organic transformations. Operational simplicity, high atom-economy, broad substrate scope, functional group tolerance and applicability towards large scale synthesis are the advantageous features of this developed methodology. [ABSTRACT FROM AUTHOR]

An efficient copper-catalyzed synthesis of pyrazolo[5,1-a]isoquinolines from 2-gem-dipyrazolylvinylbromobenzenes under mild conditions has been developed. The reaction occurred in moderate to good yields and tolerated nitrile, ether, and halogen substituted 2-gem-dipyrazolylvinylbromobenzenes. [ABSTRACT FROM AUTHOR]

We describe a photocatalyzed transformation for the synthesis of the indolo[2,1-a]isoquinoline core structure. This redox neutral reaction features mild reaction conditions and exceptional functional group tolerance. A series of valuable indolo[2,1-a]isoquinoline derivatives bearing various functional groups were synthesized using this method in good to excellent yields. [ABSTRACT FROM AUTHOR]