2161-85-5

Usage

Uses

Used in Chemical Synthesis:
4,6-Diacetylresorcinol is used as a key intermediate in the synthesis of various chemical compounds, including Schiff base ligands, hexadentate chalcogenated bisimine ligands, 1,5-benzodiazepines, ketimine of chitosan, Mannich bases, hydrazone ligands, thiosemicarbazone, semicarbazone, and thiocarbohydrazone ligands.
Used in Coordination Chemistry:
4,6-Diacetylresorcinol is used as a ligand in the formation of binuclear complexes of cobalt(II) and copper(II), as well as europium(III) complexes. These complexes have potential applications in various fields, such as catalysis, materials science, and luminescent materials.

Preparation

Preparation by Friedel–Crafts acylation of resorcinol, ? with acetic anhydride, – in the presence of zinc chloride at 142–150° for 15 min (96%) or at 150–160° for 20 min (68%); – in the presence of ferric chloride. – in the presence of concentrated sulfuric acid at 130° for 15 min (15%) ; – in the presence of 70% perchloric acid at 125–135° for 15–20 min (42%) . ? with acetyl chloride, – in the presence of zinc chloride, at 120°; – in the presence of ferric chloride, at 150° for 15 min (60%) or at reflux for 30 min ; – in the presence of concentrated sulfuric acid (18%) . ? by a typical Friedel–Crafts reaction (24%).

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 108-24-7 acetic anhydride 
• 108-46-3 recorcinol 
• 64-19-7 acetic acid 
• 2049-73-2 2,4-diethoxybenzene 
• 75-36-5 acetyl chloride 
• 3098-67-7 1,1'-(4,6-dimethoxy-1,3-phenylene)diethanone 
• 7664-93-9 sulfuric acid 
• 7446-70-0 aluminium trichloride 
• 151-10-0 1,3-Dimethoxybenzene 
• 10025-87-3 trichlorophosphate 
• 42059-48-3 acetic acid 4-acetyl-3-hydroxyphenyl ester 
• 98-95-3 nitrobenzene 
• 108-58-7 Resorcinol diacetate 

Downstream Products

• 483282-31-1 1-(2,4-dibenzoyloxy-5-acetylphenyl)-ethanone 
• 261167-21-9 4,6-diacetylbenzene-1,3-diyl bis(4-methoxybenzoate) 
• 52597-56-5 3,7-dibenzoyl-2,8-diphenyl-pyrano[3,2-g]chromene-4,6-dione 
• 858790-28-0 3,7-bis-(4-methoxy-benzoyl)-2,8-bis-(4-methoxy-phenyl)-pyrano[3,2-g]chromene-4,6-dione 
• 64857-82-5 2,4,6-triacetyl-resorcinol 
• 115540-51-7 (2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(furan-2-yl)prop-2-en-1-one) 
• 84422-38-8 3,3',5,5'-tetraacetyl-2,2',6,6'-tetrahydroxy-biphenylmethane 
• 39251-52-0 5-acetyl-2,4-bis(3-methylbut-2-enyloxy)acetophenone 
• 117690-94-5 4-(4-cyanobutoxy)-5-acetyl-2-hydroxy-acetophenone 
• 118024-34-3 C₂₆H₁₈O₁₀ 
• 87533-42-4 C₁₂H₁₈N₈O₂*2ClH 
• 109380-54-3 3,7-diphenyl-4,6-dimethyl-benzopyrane-2,8-dione 
• 85460-70-4 6-acetyl-7-hydroxy-3-phenyl-4-methylbenzopyran-2-one 
• 115705-35-6 1,1'-(4,6-dihydroxy-1,3-phenylene)bis(ethanone) dihydrazone 

Relevant academic research and scientific papers

Conductance studies on complex formation of nano Cu(NO3)2.2.5H2O with 4,6-diacetylresorcinol in mixed solvents

The different complexation thermodynamic parameters for example, formation constants (Kf), free energies of formation (?Gf), enthalpies of formation (?Hf) and entropies of formation (?Sf) for nano copper nitrate hemi pentahydrate (Cu(NO3)2.2.5H2O) with 4,6-diacetylresorcinol as a ligand in pure DMF and in mixed solvents of DMF and water are calculated at different temperatures, 293.15, 303.15, 313.15 and 323.15 K by using conductance measurements. By drawing the relation between molar conductance and ratio of metal to ligand, the figures indicate the formation of two types of complexes with M:L ratios 1:2 and 1:1 stoichiometric complexes.

Design, synthesis and characterization of bimetallic palladium complexes for terminal olefin epoxidation

A series of aromatic ring spaced binuclear Pd(II) complexes were synthesized from sterically tuned Schiff base ligands derived from 4,6-diacetylresorcinol and 2,6-dialkyl substituted anilines to provide a general and flexible set of complexes for terminal olefin epoxidation studies using "green" oxidant 30 % hydrogen peroxide as a terminal oxidant. All the compounds were fully characterized by analytical and spectrometric methods. Additionally, the ligands L1 and L2 were characterized by single crystal X-ray diffraction technique. The complexes C1 and C2 displayed high activity and substrate selectivity in the oxidation of 1-octene, whereas mixed products were observed in case of styrene with reasonable yields, arguably assignable to stringent steric and electronic factors of the complexes employed. Up to 98.5 % conversion is observed for epoxidation of 1-octene with high substrate selectivity, whereas up to 95 % conversion is observed for styrene with poor selectivity. Graphical Abstract: A series of Pd(II) complexes were synthesized from sterically tuned Schiff base ligands derived from 4,6-diacetylresorcinol and 2,6-dialkyl substituted anilines to provide a flexible set of complexes for olefin epoxidation studies using hydrogen peroxide as a terminal oxidant. The complexes C1-C3 showed substrate selectivity in the oxidation of 1-octene, where as mixed products were observed in case of styrene with reasonable yields.[Figure not available: see fulltext.]

Spectroscopic and biological studies of mono- or binuclear complexes derived from thio-Schiff bases of some transition metals

Two novel Schiff base ligands, 4,6-bis((E)-1-(2-mercaptophenylimino)ethyl) benzene-1,3-diol, H4La, and 1,2-((E)-1-(6-((E)-1-(2-mercaptophenylimino)ethyl) pyridine-2-yl)ethylideneamino)benzenthiol, H2Lb, have been synthesized by the condensation of 4,6-diacetyl resorcinol (DAR) or 2,6-diacetyl pyridine (DAP) with 2-aminobenzenthiol (ABT), in the molar ratio 1:2 [1 (DAR or DAP):2 ABT]. The structures of ligands were elucidated by elemental analysis, infrared (IR), UV-VIS as well as 1H-NMR. Reaction of the Schiff base ligands with the transition metals Co(II), Ni(II), Cu(II), Zn(II), VO(IV) and Ru(III) afforded two series of the corresponding transition metal complexes in the molar ratio 1:2 or 1:1. The ligand, H4La, behaves as tetrabasic hexadentate, which hosts the two metal ions at the centers of two SNO sites, while H2Lb acts as a compartmental dibasic pentadentate ligand forming mono- or binuclear complexes through the coordinate sites N3S2. The structures of the newly prepared complexes were characterized on the basis of the elemental analysis, spectroscopic data (IR, UV-VIS, 1H-NMR and ESR spectra along with magnetic susceptibility measurements) besides the molar conductance measurements and thermal gravimetric analyses. The bonding sites are the azomethane, sulfur atoms and phenolic oxygen for H4La or pyridine nitrogen for H2Lb. The complexes exhibit mono- or binuclear structures, distorted octahedral, tetrahedral, square planar or square pyramid structure. Synthesized compounds have also been screened for their biological activity against species of pathogenic fungi and bacteria and were found to possess appreciable fungicidal and bactericidal properties.

Spectroscopic investigations of new binuclear transition metal complexes of Schiff bases derived from 4,6-diacetylresorcinol and 3-amino-1-propanol or 1,3-diamino-propane

The bifunctional carbonyl compound; 4,6-diacetylresorcinol (DAR) serves as precursor for the formation of different Schiff base ligands, which are either di- or tetra-basic with two symmetrical sets of either O2N or N2O tridentate chelating sites. The condensation of 4,6-diacetylresorcinol with 3-amino-1-propanol (3-AP) or 1,3-diaminopropane (DAP), yields the corresponding hexadentate Schiff base ligands, abbreviated as H4La and H2Lb, respectively. The structures of these ligands were elucidated by elemental analyses, IR, mass, 1H NMR and electronic spectra. Reaction of the Schiff base ligands with copper(II), nickel(II), cobalt(II), zinc(II), cadmium(II), iron(III), chromium(III), vanadyl(IV) and uranyl(VI) ions in 1:2 molar ratio afforded the corresponding transition metal complexes. A variety of binuclear complexes for the metal complexes were obtained with the ligands in its di- or tetra-deprotonated forms. The structures of the newly prepared complexes were identified by elemental analyses, infrared, electronic, mass, 1H NMR and ESR spectra as well as magnetic susceptibility measurements and thermal gravimetric analysis (TGA). The bonding sites are the azomethine and amino nitrogen atoms, and phenolic and alcoholic oxygen atoms. The metal complexes exhibit different geometrical arrangements such as square planar, tetrahedral, square pyramid and octahedral arrangement.

Spirochromone-chalcone conjugates as antitubercular agents: Synthesis, bio evaluation and molecular modeling studies

A new series of spirochromone annulated chalcone conjugates were synthesized and evaluated for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain. These compounds were subjected to molecular modeling studies using docking and chemoinformatics based approaches. The docking simulations were performed against a range of known receptors for chalcone derived compounds to reveal MTB phosphotyrosine phosphatase B [MtbPtpB] protein as the most probable target based on the high binding affinity scores. Five compounds exhibit significant inhibition, showing minimum inhibitory concentration values i.e. MIC values ranging from 3.13-12.5 μg mL-1. Further analysis of the synthesized compounds with known and in-house developed chemoinformatics tools unequivocally established their potential as anti-tubercular compounds. QSAR modeling revealed a quantitative relationship between biological activities and frontier molecular orbital energies of synthesized compounds. The predictive model can be employed further for virtual screening of new compounds in this series.

Metal free Friedel-Crafts di-acetylation of resorcinol in acetic acid

Conventionally, the metal catalyst used for Friedel-Crafts acetylation is poisonous and the acetylating agent is not readily available. Herein, methane sulfonic acid is developed to perform Friedel-Crafts diacetylation of aromatics instead of metal catalyst. Furthermore, acetic acid is employed as acetylating agent to replace acetic anhydride. By this approach, 4,6-diacetylresorcinol, known as an indispensable intermediate in superior fiber polybenzoxazole synthesis, is prepared in high yield from resorcinol. The results obtained by 1H NMR, FT-IR and HPLC analysis indicate that methane sulfonic acid is an efficient catalyst for Friedel-Crafts acetylation and acetic anhydride can be avoid by replacement with acetic acid, in which phosphorus pentoxide is helpful to improve conversion of desired product.

Design, Synthesis and In Vivo Anxiolytic Activity of Novel Flavonoids

Worldwide millions of peoples are suffering from psychological disorders of which anxiety is one of the major and common problems. Knowing statistical reports of anxiety, the present research focused on design of new flavonoid derivatives through molecular docking by using Schr?dinger (Maestro 10.5 v), the well-known computational software on the basis of ligand – protein interaction. The most effective flavonoid derivatives with potent Glide score (IC50) values – compounds 3a (–6.824), 3b (–7.215), 3e (–6.239), 3f (-6.679), and 3j (–7.123) – were selected for the synthesis under microwave irradiation in two-step reaction involving the Claisen-Schmidth condensation to form chalcones and oxidative cyclization to form flavonoids. Then, in vivo anxiolytic activity of synthesized derivatives was studied in adult Swiss albino mice using the elevated plus-maze test model. Diazepam (2 mg/kg, IP) was used as standard drug. Compound 3b exhibited most significant anxiolytic activity against GABAA receptor, but other compounds also showed significant anxiolytic effect in mice at 100 and 200 mg/kg doses when compared to Diazepam.

4,6-Diacetylresorcinol in heterocyclic synthesis Part II: Synthesis of some novel 4,6-bis(azolyl/azinyl/ azepinyl)resorcinols

– A series of new 4,6-bis(azolyl/azinyl/azepinyl)resorcinols was synthesized in a combinatorial manner besides, (2E,2'E)-4,6-bis[3-(aminophenyl-substituted)prop-2-en-1-oxo-1-yl]resorcinols were also obtained. Heterocyclization of (2E,2'E)-4,6-bis[3-(dimethylamino)prop-2-en-1-oxo-1-yl]resorcinol (2) with nitrogen-containing binucleophiles afforded the target compounds. All the newly synthesized compounds were characterized by spectral tools.

Coordination behavior of new bis(tridentate ONO, ONS and ONN) donor hydrazones towards some transition metal ions: Synthesis, spectral, thermal, antimicrobial and antitumor studies

Three new hydrazone ligands, H2L1, H2L2 and H4L3, were prepared by condensation of 4,6-bis(1-hydrazonoethyl)benzene-1,3-diol with furan-2-carboxaldehyde, thiophene-2-carboxaldehyde and 1H-pyrrole-2-carboxaldehyde, respectively. The ligands reacted with copper(II), nickel(II), cobalt(II), zinc(II), cadmium(II) and dioxouranium(VI) ions to yield binuclear complexes formulated as [(L)M2(OAc)2(H2O)n(EtOH)m]·xH2O·yEtOH where L = L1 or L2; M = Cu, Ni, Co, Zn or Cd; n = nil, 1 or 4; m, x and y = nil or 1, [(H2L2)Cd2(OAc)4(H2O)2]·EtOH, [(L)(UO2)2(OAc)2(H2O)2Y2]·nH2O where L = L1 or L2; Y = nil or H2O; n = 2.5 or 7, [(L3)M2(H2O)6]·nH2O where M = Cu or Zn; n = 1 or 6, [(L3)(UO2)2(H2O)4]·2.5H2O and dimeric complexes; [(L1)2Ni2]·3H2O and [(H2L3)2M2]·nH2O where M = Ni or Co; n = 1.5 or 3. The ligands and their metal complexes were characterized by elemental analyses, IR, 1H and 13C NMR, electronic, ESR and mass spectra, conductivity, magnetic susceptibility measurements and powder XRD as well as thermal analysis. The coordinating sites are phenolic oxygens, azomethine nitrogens and the hetero O/N/S atoms. Octahedral, tetrahedral and square planar geometrical arrangements are proposed for metal complexes whilst the uranium ion is hepta- or octa-coordinated. The kinetics of the thermal decomposition for some metal complexes were studied and their thermodynamic parameters were calculated using Coats-Redfern method. The antimicrobial activity of the ligands and their complexes was screened. The antitumor activity of the ligands and their complexes was tested on Ehrlich Ascites Carcinoma. Copper(II) complexes showed promising IC50 values, which are comparable to that of cisplatin.

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki-Miyaura coupling reactions of aryl chlorides

A series of N,O-bidentate ligands were synthesized using the Vilsmeier-Haack reaction and oximation. 2,5-Dihydroxyterephthalaldehyde dioxime (L8) as an efficient N,O-symmetrical bidentate ligand was prepared from hydroquinone. It was studied as a high activity ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions. The coupling reactions were performed in the presence of PdCl2 as the catalyst, L8 as the ligand, Na2CO3 as the base, PEG-400 as the PTC and in ethanol/water (1?:?1) as an environmentally benign solvent at 85 °C. Plentiful biaryls were obtained by the optimized reaction with good yields at a low palladium loading of 0.20 mol%.