Synthesis Of Chromene Derivatives Research Articles

Synthesis of Chromene Derivatives from α,β‐Unsaturated Aldehydes: A Review

Chromene derivatives are important oxygen heterocycles, which are met in numerous natural products, pharmaceuticals, and organic functional materials. This review survey the achievements in the synthesis of chromenes derivatives from α,β‐unsaturated aldehydes. Particular attention is paid to the use of catalytic systems, synthetic advantages and mechanistic aspects of the reactions. The works published over the past 15 years are covered.

Synthesis and Characterization of Novel 2,4-Diaryloctahydro-2H-Chromene Derivatives with Four Stereocenters

Chromene derivatives are among the natural compounds and they can also be easily obtained synthetically. They are one of the most commonly used skeletons in heterocyclic chemistry. Chromene derivatives are used in the cosmetic and pigment industries as well as having a wide spectrum of biological activity. Synthesis of chromene derivatives and their application areas is a current topic. In this study, it is aimed to synthesis and characterization of new chromene derivatives by catalysis of molecular iodine starting from 1,5-diol derivatives with chiral centers. In this context, 8 new 2,4-diaryloctahydro-2H-chromene derivatives were synthesized in high yields and their structure determinations were made by spectroscopic methods (1H-NMR, 13C-NMR, 2D-NMR, GCMS and FTIR) and their stereochemistry was determined.

Bimetallic nanoparticles supported ionic liquid as an effective heterogeneous nanocatalyst for green synthesis of chromenes under solvent‐free conditions

In this research, a novel bimetallic nanoparticles supported by 1,3‐bis (triethoxysilylpropyl) imidazolium hydrogen sulfate ionic liquid (Ni.Cu@SiO2.BSPIm/HSO4) are designed and prepared, and its catalytic activity is investigated in organic reaction. The prepared nanocatalyst was characterized using Fourier‐transform infrared spectroscopy (FT‐IR), energy‐dispersive X‐ray, thermogravimetric analysis, field emission scanning electron microscopy, and X‐ray powder diffraction techniques. This catalyst exhibited great activity in the one‐pot synthesis of chromene derivatives through condensation reaction. The products were obtained with high purity in high to excellent yields and short reaction times. The organic products were identified by melting points, FT‐IR, and 1H NMR analyses.

A new approach for the synthesis of biologically active chromene compounds using a photo catalyst TiO2-Ag

A green and efficient method for the synthesis of chromene derivatives using TiO2 doped Ag as a photocatalyst under visible light irradiation at room temperature is reported. The advantages of our method are clean reaction condition, easy workup procedure, use of eco-friendly solvent, and recyclable catalyst and most importantly higher yield of the product. The photocatalyst was found to be highly efficient for the synthesis of chromene derivatives within a short reaction time. The photocatalyst was prepared and characterized by Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), scanning electron microscope (SEM), energy dispersive X-ray spectroscopy (EDS), and powder XRD technique and thermogravimetric analysis (TGA). In addition, the in-vitro study of helminths against S. obvelata were investigated and it was found that chromene derivatives were active against S. obvelata and showed no sign of acute toxicity in mice.

Gold(I)-Catalyzed Intermolecular Formal [4+2] Cycloaddition of O-Aryl Ynol Ethers and Enol Ethers: Synthesis of Chromene Derivatives.

Gold(I)‐catalyzed formal [4+2] cycloaddition of O‐aryl ynol ethers 1 and enol ethers 2 is described. This intermolecular reaction between two electron‐rich unsaturated systems takes place, under mild conditions, in the presence of 5 mol% [IPrAu(CH3CN)]SbF6 as catalyst giving chromene derivatives with good yields. The cycloaddition is completely regio‐ and stereoselective, as well as versatile for both reactives. Silyl enol ethers can also react in the same way and under the same reaction conditions with quantitative yields. A plausible mechanism through a selective addition of the enol ether to the alkyne gold activated complex followed by an intramolecular aromatic electrophilic substitution is proposed. Several experimental results support the presence of a cationic oxonium intermediate prior to the aromatic substitution. The reaction represents a new entry to the chromene core.

Magnesium ferrichromate nanoparticles: an efficient and recyclable catalyst in the synthesis of pyrano[2,3-c]pyrazole derivatives

Magnetically separable magnesium ferrichromate nanoparticles (MgFeCrO4 NPs) were synthesized by aqueous combustion synthesis (ACS) using glycine as the fuel. The as-synthesized powder was characterized using XRD, FTIR, SEM–EDX and SQUID techniques. Rietveld refinement studies inferred the single-phase cubic structure of the nanoferrite. Using Williamson–Hall plot, the lattice strain and the crystallite size were evaluated. Small value of lattice strain is indicative of absence of strain in the crystal lattice. The M–O bonding at the tetrahedral as well as the octahedral position was confirmed by FTIR Spectroscopy. Morphological investigations demonstrated sphere-like nanostructures with 50–100 nm particle size using SEM. Absence of any impurity in the EDX spectrum suggests formation of extremely pure MgFeCrO4 NPs. The room temperature magnetization was studied using vibrating sample magnetometer, and the nanoferrite exhibits superparamagnetic behaviour. The pyrano[2,3-c]pyrazole derivatives were synthesized in water/ethanol solvent system using MgFeCrO4 NPs heterogenous catalyst. A very short reaction time, maximum yield, easy method of separation of product and environmentally safer and milder reaction conditions are some of the advantages of our work along with the retention of catalytic activity up to five cycles. Synthesis of chromene derivatives using magnetically separable magnesium ferrichromate (MgFeCrO4).

Synthesis of the organic–inorganic hybrid catalyst via covalently anchored basic organomoieties on to the SBA-15: a recyclable catalyst for the preparation of chromene derivatives in water

In this work, for the first time, SBA supported homogeneous basic catalyst (piperazine–ethyl urea) was synthesized via a simple and convenient method. Briefly, the active homogeneous catalyst is chemically immobilized onto the SBA through silylation of hydroxyl groups to form heterogeneous catalyst that contains basic moieties. The formation of this catalyst was confirmed by elemental analysis, Fourier transform infrared spectroscopy, transmission electron microscopy, X-ray diffraction spectroscopy, thermal gravimetric analysis and Brunauer Emmett Teller. All of the characterization methods revealed that basic moieties were conveniently immobilized on to SBA as support. Therefore, it provides a novel heterogeneous basic catalyst for achieving synthetic goals. The immobilized basic catalyst provides a green and useful method for one-pot synthesis of chromene derivatives by multicomponent condensation of 4-hydroxycoumarin, 4-chlorobenzaldehyde and malononitrile. The promising points for the presented methodology are clean reaction profiles, short reaction times, simplicity in operation, catalyst with high catalytic activity and good recycle exploitation.

Silica-coated magnetic nanoparticles functionalized with piperidinium benzene-1,3-disulfonate: An efficient nanocatalyst in the synthesis of chromene derivatives

Silica-coated magnetic nanoparticles functionalized with piperidinium benzene-1,3-disulfonate: An efficient nanocatalyst in the synthesis of chromene derivatives

Protein-Promoted Synthesis of Chromene Derivatives via Biocatalytic Domino Reaction

Protein-Promoted Synthesis of Chromene Derivatives via Biocatalytic Domino Reaction

Synthesis of Chromene Derivatives via Three‐Component Reaction of 4‐hydroxycumarin Catalyzed by Magnetic Fe3O4 Nanoparticles in Water

An easy and effective procedure for one‐pot three components coupling of 4‐hydroxycumarin, isothiocyanates, and isocyanides in water by employing magnetically recoverable Fe3O4 nanoparticles is described. Variety of chromene were produced a derivatives in high yields by using of this procedure. The catalyst can be recovered and recycled without a considerable decrease in the catalytic activity.

Synthesis of Chromene Derivatives Using PS-Supported PTSA

Key words toluenesulfonic acid - heterogeneous catalysis - Brønsted acids - polystyrene - indolylchromene-carbonitriles - solvent-free

Mesoporous niobiosilicate NbMCF modified with alkali metals in the synthesis of chromene derivatives

We report the synthesis, characterization and activity of new series of catalysts based on Niobium Mesoporous Cellular Foams (NbMCF), modified with alkaline metal elements. These materials exhibit very different acid-base properties attributed to the Nb source for the preparation of the catalysts and the presence and loading of different alkaline metals.The Me/NbMCF materials (where Me are alkaline metals) were tested in the reaction of 2-hydroxybenzaldehyde and ethyl cyanoacetate, under solvent-free conditions, at room temperature, leading to mixtures of the corresponding chromenes 4 and 5, as mixtures of diastereomers erythro/threo, in a 2:1 ratio, respectively, with good to excellent yields.Our experimental results indicate that the metal loading on the catalysts and the acid-base character, and the texture parameters are probably determining factors in the reactivity and the observed diastereoselectivity.The computational study suggests that the presence of alkaline oxides on Me/NbMCF catalyst, exhibiting strong basicity, activates the formation of the nucleophile species, the corresponding enolate, and initiates the reaction. However, the cation size has a deep impact on the stability of the reactant complex so that the effective aldolization could be obstructed by the presence of the bulkier centers.

Novel domino procedures for the synthesis of chromene derivatives and their isomerization.

Novel tricyclic keto diesters have been synthesized by a one-pot three-component procedure via DABCO-catalyzed domino Knoevenagel-Michael addition reactions. Also, an efficient four-component reaction for the synthesis of another new group of tricyclic keto diesters has been developed via domino Knoevenagel-intramolecular oxo-Diels-Alder reactions. A selective thermal isomerization of the synthesized chromenes to fumarates is also described. X-ray analyses confirm unambiguously the structures of the products.

ChemInform Abstract: Iodine‐Catalyzed Synthesis of Chromene Derivatives in One Pot.

AbstractSalicylaldehydes react with 2 equiv.

Expeditious Solvent-Free Synthesis of Chromene Derivatives via Three- Component Reactions of N-Nucleophiles

Multicomponent reactions involving 4-hydroxycumarine, activated acetylenic compounds and N-nucleophiles under solvent-free conditions were investigated. The reactions could also be extended to quinoline or CH-acides. Substituted chromen could be obtained from this routine, which may have potential applications in drugs fields.