Synthesis of banana-like 1,3-dihydroxybenzene and 2,7-dihydroxynaphthalene esters and luminescence of their terbium(III) complexes

New esters of 1,3-dihydroxybenzene and 2,7-dihydroxynaphthalene with 4-(4-alkoxybenzoyloxy)-2-(or 3-)methoxybenzoic acids were synthesized. The correlation between their structure and liquid crystal properties was examined, and the luminescence characteristics of terbium(III) complexes with these esters were studied.     

A new green approach for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one derivatives using task specific acidic ionic liquid[NMP]H_2PO_4

12-Aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one derivatives were synthesized by a convenient and environmentally benign procedure involving multicomponent condensation reactions of substituted aromatic aldehydes with 2,7-dihydroxynaphthalene/2-naphthols/2,6-dihydroxynaphthlene and cyclic 1,3-dicarbonyl compounds in task specific acidic ionic liquid[NMP]H_2PO_4 at 80 ℃.This protocol has proved to be efficient in terms of good yields,operational simplicity,easy workup,recyclability of reaction medium/catalyst,and short reaction time.     

Synthesis of novel 2,2-disubstituted naphthodioxoles via an unprecedented reaction

A reaction of 2,3-dihydroxynaphthalene with ethyl-2,3-dibromo-3-phenyl-propionate or 1,3-diaryl-2,3-dibromo ketone under basic conditions led to the formation of novel 2,2-disubstituted naphthodioxoles.     

Synthesis,structure, and catalase-like activity of a novel manganese(II) complex: Dichloro[1,3-bis(2′-benzimidazolylimino)isoindoline]manganese(II)

Reaction of the ligand 1,3-bis(2′-benzimidazolylimino)isoindoline with manganese(II) chloride in acetonitrile/methanol leads to the novel mononuclear manganese(II) complex 1,3-bis(2′-benzimidazolylimino)isoindolinedichloro manganese(II) [Mn(bimindH)Cl₂], which has been characterized by various techniques such as elemental analysis, IR, UV–Vis, ESR spectroscopy, and X-ray diffraction. The ligand bimindH was synthesized by fusing phthalonitrile and 2-aminobenzimidazole at high temperature until ammonia evolution ceased. The catalase-like activity of the complex was tested in propionitrile, and it proved to be active in the dihydrogen peroxide dismutation. Based on kinetic studies the reaction is first-order in relation to both the complex and hydrogen peroxide.     

One-pot access to new tetrahydrobenzo[a]xanthen-11-ones and naphthopyranopyrimidines using 2,3-dihydroxynaphthalene

A one-pot, three-component reaction of 2,3-dihydroxynaphthalene, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds in the presence of formic acid catalyst under solvent-free conditions provides access toward a new class of tetrahydrobenzo[a]xanthen-11-ones and naphthopyranopyrimidines. The scope of the process was explored under two different reaction conditions resulting in the generation of title compounds in high yields. Moreover, the key advantages of this process are cost effectiveness of catalyst, short reaction times, easy workup, and purification of products by nonchromatographic methods.     

高纯度2,6-二羟基萘的制备工艺

以便宜的2,6-萘二磺酸钠为原料,通过一步混合碱高温碱熔法合成高纯度2,6-二羟基萘。 N₂气保护下,添加苯酚或抗氧剂1010防止过度氧化焦油的产生,能显著提高2,6-二羟基萘收率。 较佳反应条件为:2,6-萘二磺酸钠与混合碱的质量比1:3,混合碱中氢氧化钠和氢氧化钾质量比2:1,使用0.5 g苯酚或抗氧剂1010,反应温度345 ℃,反应时间2 h,碱熔收率达到86.3%。 经过甲醇-水混合溶剂精制,2,6-二羟基萘纯度能达到99%。     

Synthesis and NMR study of 9′-substituted spiroindolinonaphthoxazine derivatives

A photochromic spiroindolinonaphthoxazine derivative, 1,3,3-trimethyl-9′-hydroxy-spiro[indoline-2,3′(3H)- naphtho[2,1-b][1,4]oxazine] 3 was synthesized by condensation of 1,2,3,3-tetramethylindolenium iodide 1 and l-nitroso-2,7-dihydroxynaphthalene 2 . Further, two new derivatives, 5 and 7 , were prepared in good yields by the reactions of 3 with the hexafluoropropene trimer 4 and 4-[perfluoro(2-isopropyl-1,3-dimethyl-1-butenyl)-oxybenzoyl chloride 6 , respectively. Their unique structural features and property are discussed based on ¹H-, ¹³C- and ¹⁹F nmr spectral data.     

An IETS study of the adsorption of 2,3-dihydroxynaphthalene, 1,2-dihydroxybenzene, 1,3-dihydroxybenzene and 1,4-dihydroxybenzene on thin-film plasma-grown aluminium and magnesium oxides

Inelastic Electron Tunnelling Spectroscopy (IETs) has been applied to study the adsorption of 2,3-dihydroxynaphthalene, 1,2-dihydroxybenzene, 1,3-dihydroxybenzene and 1,4-dihydroxybenzene onto plasma-grown thin-film partially hydroxylated magnesium and aluminium oxides. For both 2,3-dihydroxynaphthalene and 1,2-dihydroxybenzene on aluminium oxide it is found that adsorbate chemisorption involves reaction of the two hydroxyl groups present in the adsorbate to form a di-anion in the case of the former and both the mono- and di-anion for the latter. The tunnel spectra for both compounds on magnesium oxide indicate that the di-anion is formed. Adsorption at the oxide surfaces for these two adsorbates involves adsorbate deprotonation with the formation, at the oxide surface, of molecular water which is subsequently desorbed and pumped away during sample junction preparation. For the 1,3- and 1,4-dihydroxy systems, on both oxides, the presence of a strong ν(OH) band at ≈3650 cm⁻¹ suggests that only one of the hydroxyl groups present in both systems is involved in adsorbate deprotonation interactions at the respective oxide surfaces, with the second hydroxyl group present contributing to the enhanced substrate oxide ν(OH) envelope observed.     

Synthesis and characterization of novel fluorinated polyimides derived from 1,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic dianhydrides

A new structurally asymmetric diamine monomer containing flexible ether linkages and bulky trifluoromethyl substituents, namely 1,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene, was prepared from 1,3-dihydroxynaphthalene and 2-chloro-5-nitrobenzotrifluoride. New series of fluorinated polyimides were synthesized from the diamine with six commercially available aromatic tetracarboxylic dianhydrides using a conventional two-stage process with thermal or chemical imidization. The resulting polyimides were highly soluble in a variety of organic solvents and could afford transparent and tough films via solution casting. These polyimides exhibited moderately high glass-transition temperatures (by DSC) of 236-268 °C and softening temperatures (by thermomechanical analysis) of 231-250 °C, and they did not show significant decomposition before 500 °C under either nitrogen or air atmosphere. Also, they revealed low moisture absorptions (0.32-0.78%), low dielectric constants (2.81-3.24 at 10 kHz), and high optical transparency (ultraviolet-visible absorption cutoff wavelengths of 377-426 nm).     

Synthesis of Aminomethyl Derivatives of 2,6-Dihydroxynaphthalene

Russian Journal of Organic Chemistry - Mono- and bis-aminomethyl derivatives of 2,6-dihydroxynaphthalene containing cyclic amine residues have been synthesized, and the formation of a strong...     

Synthesis and structures of cis -WO2 complexes with 2,3-dihydroxynaphthalene

{Na(OCH₃)[H₃N(CH₂)₂NH₂]₂}[WO₂(C₁₀H₆O₂)₂] (1) was obtained by the reaction of Na₂WO₄ · 2H₂O with 2,3-dihydroxynaphthalene and ethylenediamine. [H₂N(CH₂)₃NH₃]₂[WO₂(C₁₀H₆O₂)₂] (2) was synthesized by the reaction of Na₂WO₄ · 2H₂O with 2,3-dihydroxynaphthalene and 1,3-propylenediamine. Complex 1 was a one-dimensional chain-like structure and the Na atom is in the structure, while complex 2 was a discrete monomer without Na in its structure. The two complexes were synthesized in the same reaction conditions, except that protonated ethylenediamine was used in reaction 1, but 1,3-propylenediamine in reaction 2.     

On the synthesis of geminally functionalized heterocyclic aminocarboxylic acid esters

The title compounds 5 can be easily obtained by two alternative procedures: 1,3-dipolar cycloaddition to benzamidocinnamates 3 prepared by methanolysis of the corresponding oxazolones 1 or methanolysis of the spirooxazolones 4 synthesized by 1,3-dipolar cycloaddition to oxazolones 1 . Both reaction sequences show the same stereo and regioselectivity.     

Synthesis and studies of homopolycyanurates based on 2-carbazol-4,6-dichloro-s-triazine

Eight homopolycyanurates have been synthesized by interfacial polycondensation of 2-carbazol-4,6-dichloro-s-triazine with 1,7-dihydroxynaphthalene, 1,4-dihydroxyanthraquinone, ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,4-butanediol and 1,8-dihydroxyanthraquinone. All the homopolycyanurates synthesized were characterized for their solubility, density, viscosity, IR, NMR spectral and thermogravimetric parameters.     

Synthesis and Mesomorphic Properties of New 3-Aryl-5-cyano-4,5-dihydroisoxazoles

New 3-aryl-5-cyano-4,5-dihydroisoxazoles possessing liquid crystalline properties were synthesized in two ways. The key stage in both procedures is 1,3-dipolar cycloaddition of nitrile oxides to acrylonitrile.     

铜(Ⅱ)-2-QADNm络合物电分析性能研究

本文研究了铜(Ⅱ)与2-QADNm形成的络合物的极谱行为。用改进的单纯形法优化了底液条件,研究了Cu(Ⅱ)-2-QADNm体系的电分析特性;提出了用2-QADNm借络合物吸附波测定痕量铜的方法,测定低限为10^-8mol/L。     

Bis(1,3-dithiole-2-chalcogenones) and tetrathiafulvalenes in the synthesis of bridged tetrathiafulvalene-containing structures

Bis(1,3-dithiole-2-chalcogenones) in which the 1,3-dithiole fragments are linked through various bridging groups were synthesized by different methods. Some of these compounds were converted into substituted tetrathiafulvalenes with bridged 1,3-dithiole rings. The same structures were synthesized from preliminarily prepared symmetric tetrathiafulvalenes containing 2-cyanoethylsulfanyl groups in both 1,3-dithiole rings. Similar spacers were used to bridge two tetrathiafulvalene fragments. Syntheses of the involved initial compounds were described.     

Synthese und Eigenschaften einiger neuer hydroxylsubstituierter Laserfarbstoffe auf Cumarinbasis Lumineszierende Heterocyclen, 8. Mitt.

Condensation of ethyl acetoacetate with 1,3-, 1,6-and 2,7-dihydroxynaphthalene, resp., as well as with 4,7-dihydroxycoumarin affords four new coumarines (1–4). The pyronocoumarin system of4 may alternatively be synthesized by reacting 3-anilinomethylene-7-hydroxy-2,4-chromandione with nitriles such as ethyl cyanoacetate, malodinitrile, cyanoacetamide, 4-nitrophenylatonitril or -cyanoacetophenone to give the strongly fluorescent pyrones5 a-e. The solvent and acidity dependent absorption and emission spectra are presented.2, 3, 4 and5 a-c lase very efficiently, giving green, yellow or red laser light.

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7. Mitt.:O. S. Wolfbeis, Mh. Chem.109, 905 (1978).     

Chemistry of phenols: Recent advances in the chemistry of 2,3-dihydroxynaphthalene and the related analogues

This review describes the chemistry of 2,3-dihydroxynaphthalene and the related analogues. The synthetic routes reported to obtain the investigated structures are discussed. In addition, the reactivity and the synthesis of fused heterocyclic systems containing one or two heteroatoms are discussed. The compounds derived from 2,3-dihydroxynaphthalene are located in the basic skeleton of several natural drugs. The products were applied in the fields of polymer chemistry, physical chemistry, and medicinal chemistry. The different sections cover: methods of preparation, reactions, heterocyclic systems, macrocycles, organosilicon derivatives, coordination chemistry, and biological importance. The assessment relates to the recent reports and contains a short, targeted survey of the title compound for the past 15 years.     

Cyclobisphosphorylation of 1,7-Dihydroxynaphthalene with Phosphorous Triamides

Cyclobisphosphorylation of dihydroxynaphthalenes was studied with the aim to prepare organo- phosphorus aromatic compounds containing intramolecular cavities. The design and the structural and chemical features of cyclobisphosphites prepared from unsymmetrical 1,7-dihydroxynaphthalene are con- sidered. New data are reported on regioselective cyclophosphorylation of 1,7-dihydroxynaphthalene by dis- proportionation of its bis(diamidophosphorylated) derivatives.     

Regioselective oxidative polymerization of 1,5-dihydroxynaphthalene catalyzed by bilirubin oxidase in a water–organic solvent mixed solution

Bilirubin oxidase (EC1.11.1.7) was used to catalyze the oxidative polymerization of 1,5-dihydroxynaphthalene to its polymer in a mixed solvent composed of dioxane, ethyl acetate, and acetate buffer. In an aqueous solution, the enzymatic oxidative polymerization hardly occurred and resulted in negligible yield mainly due to the poor solubility of 1,5-dihydroxynaphthalene. In the mixed solvent the conversion proceeded with a yield of ca. 70%. The polymer yield was studied with respect to reaction time and solvent components. Elemental analysis, UV-visible, fluorescent, and FT-IR spectroscopic analyses, proton NMR and electrochemical studies, and solubility in various organic solvents revealed that 1,5-dihydroxynaphthalene is polymerized by the C? C coupling. The molecular weight of the polymeric products solubilized with DMF varied from low molecular weight product to high molecular weight polymer. From the chromatographic studies, the organic solvent–insoluble residue was suggested to be highly polymerized material. Based on these findings a possible mechanism for enzymatic polymerization of 1,5-dihydroxynaphthalene is presented: less stable intermediates produced enzymatically from 1,5-dihydroxynaphthalene undergo coupling and polymerization to ortho-1,5-dihydroxynaphthalene polymer, thereby resulting in a regioselective polymerization of 1,5-dihydroxynaphthalene. © 1993 John Wiley & Sons, Inc.