One-pot multicomponent green LED photoinduced synthesis of chromeno[4,3-b]chromenes catalyzed by a new nanophotocatalyst histaminium tetrachlorozincate

Histaminium tetrachlorozincate nanoparticles are prepared, characterized and applied as an effective and recoverable photocatalyst in the one-pot, green and multi-component synthesis of various chromenes by the reaction of dimedone and/or 1,3-cyclohexanedione, arylaldehyde and 4-hydroxycoumarin in high yields under solventless conditions at ambient temperature. This new catalyst is characterized by FT-IR, XRD, EDX, NMR, SEM and TEM techniques. The incorporation of histaminium ions into the framework of ZnCl₄²⁻ significantly affected the photocatalytic activity of tetrachlorozincate such that good reusability and recyclability are attained. Moreover, reactive species such as ˙O₂⁻ and hydroxyl radicals have proved to be active species in the presented photocatalytic reaction. In addition, the hot filtration test confirms enough stability of the photocatalyst and no significant leaching and destruction of the framework in the course of the reaction. The major advantages of the presented methodology include easy work-up, cost effectiveness, nontoxic nature, broad substrate scope, 100% atom economy, ease of separation, and environment friendly reaction conditions. Finally, the catalyst could be reused many times without significant loss of activity.

(His.)ZnCl₄ nanocatalyst is realized for the preparation of chromenes with a green LED. ˙O₂⁻, OH˙ and h⁺ are reactive species for this reaction. Complementary tests assured good stability and reusability of the nanophotocatalyst.     

One-pot synthesis and property study on thieno[3,2-b]furan compounds

Based on the regioselective intermolecular Suzuki coupling and subsequent intramolecular Ullmann C–O coupling reactions, one-pot synthesis of benzo[4,5]thieno[3,2-b]benzofurans (BTBFs) was developed after optimization of the reaction conditions including catalysts, solvents, bases, ligands and reaction times. The one-pot reaction, with only 2 mol% Pd(PPh₃)₄ and 2 mol% copper(i) thiophene-2-carboxylate (CuTc) as the catalysts, K₃PO₄·3H₂O as the base and tert-butanol as the solvent, afforded moderate to good yields (up to 70%) for a variety of substrates.

Based on the regioselective intermolecular Suzuki coupling and subsequent intramolecular Ullmann coupling reactions, one-pot synthesis of benzo[4,5]thieno[3,2-b]benzofurans (BTBFs) has been developed.     

An efficient multicomponent synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetic nanoparticle supported Lewis acidic deep eutectic solvent

A mild and highly efficient reaction for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetically supported Lewis acidic deep eutectic solvent on magnetic nanoparticles (LADES@MNP) has been developed via one-pot multicomponent processes under solvent-free sonication. These reactions have good to excellent yields, mild conditions, and work-up simplicity. This method represents a new method for the preparation of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. More importantly, LADES@MNP can be easily recovered by magnetic separation and reused five times without significant loss of catalytic activity.

A mild and highly efficient method for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a Lewis acidic deep eutectic solvent on magnetic nanoparticles (LADES@MNP).     

Correction: An efficient multicomponent synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetic nanoparticle supported Lewis acidic deep eutectic solvent

Correction for ‘An efficient multicomponent synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetic nanoparticle supported Lewis acidic deep eutectic solvent’ by Thanh Thi Nguyen et al., RSC Adv., 2019, 9, 38148–38153, DOI: 10.1039/C9RA08074K.

The authors apologise that a related reference, given here as ref. 1–5, was not cited in the original article. On page 38148, in the first paragraph of the Introduction, a citation to the reference should be added at the end of the sentence beginning “Among them, Lewis acidic…”. The paragraph should be changed as follows “In past decade, deep eutectic solvents (DESs) have attracted much attention in both reaction media and catalysts due to their unique properties such as wide liquid range, biodegradability, excellent thermal stability, and negligible vapor pressure.^1,2 Among them, Lewis acidic deep eutectic solvents (LADESs) have been intensively studied as efficient media for organic syntheses.^3–5”.The Royal Society of Chemistry apologises for these errors and any consequent inconvenience to authors and readers.     

Convenient construction of tetrahydrochromeno[4′,3′:2,3]indolizino[8,7-b]indoles and tetrahydroindolizino[8,7-b]indoles via one-pot domino reaction

The functionalized tetrahydrochromeno[4′,3′:2,3]indolizino[8,7-b]indoles were conveniently synthesized in high yields by one-pot domino reaction of tryptamines, alkyl propiolates and 2-aryl-3-nitro-2H-chromenes. Under similar conditions, the one-pot reaction of tryptamines, alkyl propiolates and β-nitroalkenes resulted in functionalized tetrahydroindolizino[8,7-b]indoles. The reaction mechanism involved sequential generation of β-enamino ester, Michael addition, Pictet–Spengler reaction and annulation process. The reaction showed high atomic economy and met the goals of sustainable chemistry.

The functionalized tetrahydrochromeno[4′,3′:2,3]indolizino[8,7-b]indoles were conveniently synthesized in high yields by one-pot domino reaction of tryptamines, alkyl propiolates and 2-aryl-3-nitro-2H-chromenes.     

Structure-based discovery and bio-evaluation of a cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one as a phosphodiesterase 10A inhibitor

Phosphodiesterase10A (PDE10A) is a potential therapeutic target for the treatment of several neurodegenerative disorders. Thus, extensive efforts of medicinal chemists have been directed toward developing potent PDE10A inhibitors with minimal side effects. However, PDE10A inhibitors are not approved as a treatment for neurodegenerative disorders, possibly due to the lack of research in this area. Therefore, the discovery of novel and diverse scaffolds targeting PDE10A is required. In this study, we described the identification of a new PDE10A inhibitor by structure-based virtual screening combining pharmacophore modelling, molecular docking, molecular dynamics simulations, and biological evaluation. Zinc42657360 with a cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one scaffold from the zinc database exhibited a significant inhibitory activity of 1.60 μM against PDE10A. The modelling studies demonstrated that Zinc42657360 is involved in three hydrogen bonds with ASN226, THR187 and ASP228, and two aromatic interactions with TYR78 and PHE283, besides the common interactions with the P-clamp residues PHE283 and ILE246. The novel scaffold of Zinc42657360 can be used for the rational design of PDE10A inhibitors with improved affinity.

Phosphodiesterase10A (PDE10A) is a potential therapeutic target for the treatment of several neurodegenerative disorders.     

Antifungal properties in a novel series of triazino[5,6-b]indoles.

GR99060 and GR99062 are representatives of a series of 1,2,4-triazino[5,6-b]indole compounds. This series possessed broad-spectrum antifungal activity in vitro. The MIC ranges of the two compounds were as follows: 0.25 to 4 micrograms/ml for Candida albicans, 0.25 to 16 micrograms/ml for Candida sp., 1 to 8 micrograms/ml for Aspergillus spp., and 0.25 to 16 micrograms/ml for Cryptococcus neoformans. GR99062 was metabolized in vitro by a mouse liver microsomal preparation, while GR99060 was stable. GR99060 was efficacious in a murine model of systemic candidiasis by oral or parenteral administration, although no clear dose-response was achieved, suggesting that other factors adversely affected the compound's in vivo activity.     

Recent advancements in the multicomponent synthesis of heterocycles integrated with a pyrano[2,3-d]pyrimidine core

Heterocyclic compounds incorporated with a pyranopyrimidine skeleton have received substantial consideration owing to their privileged, and intelligible biodiversity. Accordingly, this review highlights the multicomponent synthetic routes adopted to prepare heterocyclic compounds incorporated with the pyrano[2,3-d]pyrimidine skeleton in the preceding two years. The different sections comprise the synthesis of bicyclic, tricyclic, polycyclic, and spirocyclic systems along with the estimation of the probable mechanistic routes for the reaction pathways. Commonly, the pyran ring closure was the major idea of most studies, and the mechanistic pathways of these reactions involved Knoevenagel condensation, Michael addition, and intramolecular cyclocondensation. Besides, the significant biological potency of the compounds recently synthesized from multicomponent reactions is deliberated.

The present review highlighted the recent developments of the multicomponent synthesis of heterocyclic compounds with pyrano[2,3-d]pyrimidine skeleton applying the diverse strategies.     

Microwave-assisted multicomponent synthesis of antiproliferative 2,4-dimethoxy-tetrahydropyrimido[4,5-b]quinolin-6(7H)-ones

In this study, we demonstrate a simple, highly efficient, rapid and convenient series of 2,4-dimethoxy-tetrahydropyrimido[4,5-b]quinolin-6(7H)-ones 4a–v. Microwave irradiation facilitates the one-pot multicomponent reaction of different aromatic aldehydes, 6-amino-2,4-dimethoxypyrimidine and dimedone using glacial acetic acid. Metal-free multicomponent synthesis, shorter reaction time, higher product yield, easy product purification without column chromatography and outstanding green credential parameters are the key features of this protocol. We analysed 4a–v against six human tumour cell lines for antiproliferative activity. 4h, 4o, 4q and 4v show good antiproliferative activity with a good in silico ADMET profile. Furthermore, 4h, 4o, 4q and 4v also show drug-likeness properties by obeying drug-like filters.

Herein, we demonstrate a simple, rapid and green synthesis of 2,4-dimethoxy-THPQs under microwave irradiation and their antiproliferative activity, in silico ADMET and drug-likeness studies were carried out.     

Nano-kaolin/Ti4+/Fe3O4: a magnetic reusable nano-catalyst for the synthesis of pyrimido[2,1-b]benzothiazoles

Herein, nano-kaolin/Ti⁴⁺/Fe₃O₄ as a new magnetic nano-catalyst was synthesized, and its structural properties were characterized using various techniques such as Fourier transform infrared (FTIR) spectroscopy, field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), a vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA) and energy-dispersive X-ray spectroscopy (EDX). This catalyst was used for the synthesis of pyrimido[2,1-b]benzothiazoles via the one-pot condensation of 2-aminobenzothiazole, an aldehyde and β-keto ester under solvent-free conditions at 100 °C. This simple protocol has many advantages such as easy workup, high product yields, short reaction times and reusability of the catalyst.

Herein, nano-kaolin/Ti⁴⁺/Fe₃O₄ as a new magnetic nano-catalyst was synthesized, and its structural properties were characterized using various techniques such as FTIR spectroscopy, FE-SEM, TEM, XRD, VSM, TGA and EDX.     

Nano-[Fe3O4@SiO2/N-propyl-1-(thiophen-2-yl)ethanimine][ZnCl2] as a nano magnetite Schiff base complex and heterogeneous catalyst for the synthesis of pyrimido[4,5-b]quinolones

Nano-[Fe₃O₄@SiO₂/N-propyl-1-(thiophen-2-yl)ethanimine][ZnCl₂] as a nano magnetite Schiff base complex was designed and fully characterized by various analyses such as Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric analysis (DTA), vibrating sample magnetometry (VSM), scanning electron microscopy (SEM), and transmission electron micrographs (TEM). The presented nano magnetite Schiff base complex was used as a heterogeneous catalyst for the synthesis of pyrimido[4,5-b]quinolones by the reaction of aryl aldehyde, dimedone and 6-amino-1,3-dimethyluracil in EtOH : H₂O (7 : 3) as a solvent at 60 °C.

Nano-[Fe₃O₄@SiO₂/N-propyl-1-(thiophen-2-yl)ethanimine][ZnCl₂] as a nano magnetite Schiff base complex was designed and successfully tested for the synthesis of pyrimido[4,5-b]quinolones.     

One-pot synthesis of 2-amino-4H-chromene derivatives by MNPs@Cu as an effective and reusable magnetic nanocatalyst

In this research, MNPs@Cu as an effective and recyclable nanocatalyst was prepared and characterized using different methods including Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), vibrating sample magnetometry (VSM), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), and X-ray diffraction (XRD). After the characterization of this new nanocatalyst, it was efficiently used for the promotion of the one-pot synthesis of 2-amino-4H-chromene derivatives via one-pot three-component reaction of the enolizable compound, malononitrile, and arylaldehydes under solvent-free conditions at 90 °C. The procedure gave the desired products in high-to-excellent yields in short reaction times. Also this catalyst, because of its magnetic nature, can be simply restored by a permanent magnetic field and comfortably reused several times without any significant loss of its catalytic activity.

MNPs@Cu as an effective, recyclable nanocatalyst was prepared and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis vibrating sample magnetometry, scanning electron microscopy, energy dispersive X-ray spectroscopy and X-ray diffraction.     

Eco-friendly synthesis of fused pyrano[2,3-b]pyrans via ammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds

Various substituted polycyclic pyrano[2,3-b]pyrans were synthesized via the condensation of 4H-chromene-3-carbaldehydes and their areno-condensed analogues with hetero- and carbocyclic 1,3-dicarbonyl compounds in acetic acid. Ammonium acetate was used as a green catalyst for the reaction. The process also involves the subsequent Knoevenagel condensation and 6π-electrocyclization of the 1-oxatriene intermediates formed. Fused pyridines were isolated as the products of the conjugated addition of ammonia to 1-oxatriene intermediates while using carbocyclic 1,3-dicarbonyl compounds and increasing the reaction time, indicating the reversibility of the electrocyclization stage. The calculated values of the Gibbs free energies and reaction rate constants for the 1-oxatriene – 2H-pyran equilibrium also testified to the irreversibility of pyrano[2,3-b]pyran formation in the case of using of heterocyclic 1,3-dicarbonyl compounds.

We report the eco-friendly synthesis of fused pyrano[2,3-b]pyrans via ammonium acetate-mediated formal oxa-[3 + 3]-cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds.     

A multicomponent,facile and catalyst-free microwave-assisted protocol for the synthesis of pyrazolo-[3,4-b]-quinolines under green conditions

A facile, swift and ecofriendly microwave-assisted multi-component/one-pot protocol is designed for the synthesis of novel pyrazolo-[3,4-b]-quinolines at ambient temperature in aqueous ethanol as a reaction medium. The 18 novel pyrazolo-[3,4-b]-quinoline derivatives were synthesized by fusion of chosen aryl aldehyde, dimedone and 5-amino-3-methyl-1-phenylpyrazole in excellent yields (91–98%). All the molecular structures were confirmed by ¹H-NMR, ¹⁵N-NMR, ¹³C-NMR, and HRMS data analysis. Operational simplicity, easy handling, one-step simple workup procedure, mild reaction conditions, short reaction time (≤10 min), high selectivity and no by-product formation are the striking features of the protocol.

A facile, swift and ecofriendly microwave-assisted multi-component/one-pot protocol is designed for the synthesis of novel pyrazolo-[3,4-b]-quinolines at ambient temperature in aqueous ethanol as a reaction medium.     

An attempt to synthesize a terthienyl-based analog of indacenedithiophene (IDT): unexpected synthesis of a naphtho[2,3-b]thiophene derivative

We report herein our attempt to synthesize an analog of indacenedithiophene (IDT) based on a tetraphenylhexyl substituted, covalently bridged syn-terthienyl unit. Instead of the expected compound the adopted synthetic route led to the formation of an unexpected, new naphtho[2,3-b]thiophene derivative. The structure of this compound was fully characterized by NMR and HRMS as well as single crystal X-ray diffraction and its electronic properties have been analyzed by UV-vis absorption spectroscopy and cyclic voltammetry. A possible mechanism for the formation of this compound is also proposed on the basis of detailed theoretical investigations.

Serendipitous synthesis of a novel naphtho[2,3-b]thiophene derivative. Detailed investigation of the structure and properties as well as a possible mechanism for its formation.     

Enantioselective Michael reaction of anthrone catalyzed by chiral tetraoxacalix[2]arene[2]triazine derivatives

A highly enantioselective Michael addition reaction of anthrone with nitroalkenes by chiral tetraoxacalix[2]arene[2]triazine catalysts was investigated as a novel topic. The stereoselective conversion progressed smoothly by employing 10 mol% of the catalyst and afforded the corresponding Michael adducts with acceptable to high enantioselectivities (up to 97% ee) and very high yields (up to 96%).

A highly enantioselective Michael addition reaction of anthrone with nitroalkenes by chiral tetraoxacalix[2]arene[2]triazine catalysts was investigated as a novel topic.     

Facile synthesis of 2-substituted benzo[b]furans and indoles by copper-catalyzed intramolecular cyclization of 2-alkynyl phenols and tosylanilines

A catalytic amount of CuCl and Cs₂CO₃ was employed to synthesize a variety of 2-substituted benzo[b]furans and indoles by an intramolecular cyclization of 2-alkynyl phenols and tosylanilines. This protocol features mild conditions, high yields and broad substrate scope, which makes it a practical method for the synthesis of 2-substituted benzo[b]furans and indoles.

A facile and inexpensive copper-catalyzed method was developed for the synthesis of 2-substituted benzo[b]furans and indoles.     

Synthesis of 2-ethoxycarbonylthieno[2,3-b]quinolines in biomass-derived solvent γ-valerolactone and their biological evaluation against protein tyrosine phosphatase 1B

A series of 2-ethoxycarbonylthieno[2,3-b]quinolines were synthesized in the bio-derived “green” solvent γ-valerolactone (GVL) and evaluated for their inhibitory activities against PTP1B, the representative compound 6a displayed an IC₅₀ value of 8.04 ± 0.71 μM with 4.34-fold preference over TCPTP. These results provided novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs.

A series of 2-ethoxycarbonylthieno[2,3-b]quinolines were synthesized in the bio-derived “green” solvent γ-valerolactone and evaluated for their inhibitory activities against PTP1B, compound 6a displayed an IC₅₀ value of 8.04 ± 0.71 μM with 4.34-fold preference over TCPTP.     

ACI/EG eutectic mixture mediated synthesis,characterization and in vitro osteoblast differentiation assessment of spiropyrrolo[1,2-b]isoquinoline analogues

An eco-friendly acetylcholine iodide–ethylene glycol (ACI/EG) deep eutectic mixture mediated green protocol has been developed for the synthesis of hitherto unexplored multi-functionalized linear tricyclic spiropyrrolo[1,2-b]isoquinoline analogues. The effects of the synthesized compounds on the osteoblast differentiation of hBMSC-TERT cell lines were investigated and promising results were observed with significant IC₅₀ values. In addition, molecular modeling simulations were also performed with the 3D structure of BMP-2 to reveal binding interactions and orientations of highly potent spiropyrrolo[1,2-b]isoquinoline analogues.

An eco-friendly acetylcholine iodide–ethylene glycol (ACI/EG) deep eutectic mixture mediated green protocol has been developed for the synthesis of unexplored multi-functionalized linear tricyclic spiropyrrolo[1,2-b]isoquinoline analogues.