General non-catalytic approach to spiroacenaphthylene heterocycles: multicomponent assembling of acenaphthenequinone,cyclic CH-acids and malononitrile

The new type of non-catalytic cascade reaction was found: the direct multicomponent reaction of acenaphthenequinone, cyclic CH-acids, and malononitrile to form spiroacenaphthylene heterocycles. The direct heating in water acenaphthenequinone, cyclic CH-acids, and malononitrile at 80 °C results in the formation of spiroacenaphthylene heterocycles in 90–95% yields. Thus, a new simple and efficient green ‘one-pot’ method to synthesize substituted spiroacenaphthylene frameworks was found directly from simple starting compounds. The application of this convenient green multicomponent method is also beneficial from the viewpoint of diversity-oriented large-scale processes.     

New functionalized acenaphthene-1,2-diimines and derived zinc and copper complexes

Russian Chemical Bulletin - The new compound 1,2-bis[(2,6-diisopropyl-4-iodophenyl)imino]acenaphthene (I2-dppbian, 1) was synthesized by the condensation of acenaphthenequinone with...     

Facile synthesis of novel dispiroheterocylic derivatives through cycloaddition of azomethine ylides with acenaphthenone-2-ylidine ketones

The regioselective synthesis of a series of novel dispiropyrrolidines and dispiropyrrolizidines has been accomplished through intermolecular 1,3-dipolar cycloaddition of azomethine ylides obtained from 1,2-diones like isatin and acenaphthenequinone with acenaphthenone-2-ylidine ketone dipolarophiles in methanol under reflux conditions.     

Photochemical Synthesis and Characterization of 8,9-Dihydroacenaphtho-[1,2-b][1,4]Dioxins

The orange-red 8,9-dihydroacenaphtho[1,2-b] [1,4]dioxins were synthesized by the photo-Diels-Alder reaction of acenaphthenequinone with the corresponding alkenes. The products were characterized by spectroscopic and X-ray methods.     

A versatile A2 + B3 approach to hyperbranched polyacenaphthenequinones

A series of hyperbranched polyacenaphthenequinones has been prepared by superelectrophilic aromatic substitution of (substituted) acenaphthenequinone and 1,3,5‐tris‐(4‐phenoxybenzoyl)benzene via a facile A₂ + B₃ approach. Because of the strongly increased reactivity of the second A functionality, gelation was efficiently avoided during the polymerization. The structure of the resulting polymer was characterized by NMR spectroscopy and gel permeation chromatography. Further modification of the hyperbranched polyacenaphthenequinone was explored both on the acenaphthenequinone and aromatic moieties. Moreover, the polymer modified through sulfonation was investigated as a water‐soluble acid catalyst for the degradation of biomass resources. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 2596‐2603     

Convenient synthesis of spiro[indoline-3,4'-pyrano[2,3-c]pyrazole] and spiro[acenaphthyl-3,4'-pyrano[2,3-c]pyrazoles] via fourcomponent reaction

The base promoted four-component reaction of hydrated hydrazine, dimethyl acetylenedicarboxylate, isatines and malononitrile (ethyl cycanoacetate) in ethanol afforded polysubstituted spiro[indoline-3,4‘-pyrano[2,3-c]pyrazoles] and spiro[acenaphthyl-3,4-pyrano[2,3-c]pyrazoles]     

具有平面结构的四齿肼基硫代甲酸苄酯席夫碱镍配合物的合成,晶体结构和三阶非线性光学性质研究

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Four‐Component Reaction for Efficient Construction of Spiro[acenaphthylene‐1,2′‐quinoline] skeleton

The four‐component reactions of anilines, dialkyl acetylenedicarboxylate, acenaphthenequinone, and dimedone (or cyclohexane‐1,3‐dione) in acetic acid provided an efficient synthetic procedure for the functionalized spiro[acenaphthylene‐1,2′‐quinoline] derivatives in good yields. This reaction has the advantages of using common starting material, mild reaction conditions, and operational simplicity.     

An easy access to novel steroidal dispiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides

A facile one-pot synthesis of novel steroidal dispiropyrrolidines has been accomplished by 1,3-dipolar cycloaddition reaction of various azomethine ylides derived from isatin/acenaphthenequinone/ninhydrin and sarcosine with various estrone derivatives as dipolarophiles, in good yield. The effect of various solvents on the 1,3-dipolar cycloaddition reaction are also studied.     

Design of Schiff Base-Like Postmetallocene Catalytic Systems for Polymerization of Olefins: III. Synthesis of 1,2-Bis-(arylimino)acenaphthenes Having Cyclic Substituents

Reactions of substituted cycloalkylanilines with acenaphthenequinone in a mixture of methanol with methylene chloride afforded a number of the corresponding 1,2-is(cycloalkylarylimino)acenaphthenes. The products may be used as ligands for the synthesis of nickel complexes which are capable of catalyzing olefin polymerization at elevated temperature in the presence of methylaluminoxane.     

Synthesis of a Novel Dispiroheterocyclic Framework via the Regioselective 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylides

2‐Arylidene‐1,3‐indanediones undergo regioselective 1,3‐dipolar cycloaddition with the azomethine ylide generated from acenaphthenequinone and sarcosine to afford a rare class of complex dispiropyrrolidines in good yield. Single‐crystal X‐ray crystal analysis of one of the products confirms the structure and regiochemistry of the cycloaddition.     

Using ring strain to inhibit a decomposition path: first synthesis of an Alkyl-BIAN ligand (Alkyl-BIAN = bis(alkyl)acenaphthenequinonediimine)

N-Alkyl imines of acenaphthenequinone are not stable because an isomerization occurs that releases part of the ring strain of the initially formed imine by changing the hybridization of one of the ring carbon atoms from sp(2) to sp(3); however, if an even more strained ring is present in the alkyl group, the isomerization becomes unfavorable and the compound is stable.     

Chemoselective Synthesis of Novel Heterocyclic [3.3.3]Propellane Derivatives via a One‐pot Three‐component Reaction

A highly chemoselective method for the synthesis of heterocyclic [3.3.3]propellane derivatives was developed via sequential three‐component reactions of acenaphthenequinone, malononitrile/cyanoacetate and a variety of 1,3‐dicarbonyl compounds under mild conditions in ethanol. A plausible mechanism for this type of reaction was proposed. The value of this method was highlighted by its high selectivity, simple procedures, and good yields.     

Reduction of 1,2-dicarbonyl compounds and of their N-phenylimine derivatives by sodium cyanide under aprotic conditions

Some aromatic 1,2-dicarbonyl compounds, i.e. 9,10-phenanthrenequinone, acenaphthenequinone and benzil, and their corresponding N-phenyl monoimines, have been reduced, using dry acetonitrile as the solvent, in the presence of sodium cyanide as a reducing agent. Comparative potentiostatic preparative-scale electrolysis is described.     

A facile entry into a novel class of dispiroheterocyclic framework through 1,3-dipolarcycloaddition of azomethine ylides with 3-arylidene-4-chromanones as dipolarophiles

The cycloaddition reaction of azomethine ylides, generated through decarboxylation, with (E)-3-arylidene-4-chromanones as dipolarophiles has been investigated. A high degree of regioselectivity has been observed in the synthesis of a new class of functionalized dispiroheterocyclic compounds bearing chromanone and acenaphthenequinone framework. The structures were established by spectroscopic techniques as well as single crystal X-ray analysis.     

Synthesis and structure of m-terphenyl-based cyclophanes with nitrogen intra-annular functional groups

[structure: see text] Herein we describe an efficient synthesis of cyclophanes comprised of intra-annular nitrogen functional groups through a template-promoted cyclization by ring-closing metathesis (RCM). The synthesis proceeds through condensation of meta-styryl anilines with acenaphthenequinone to form the templates, followed by RCM with Grubb's second-generation catalyst to afford cyclophanes with internal alpha-diimine functionality. Prolonged hydrogenation efficiently removes the template to provide a macrocycle containing the diamine functionality.     

Multicomponent approaches to 8-carboxylnaphthyl-functionalized pyrazolo[3,4-b]pyridine derivatives

A simple and novel protocol for the efficient synthesis of a series of 8-carboxylnaphthyl functionalized pyrazolo[3,4-b]pyridine derivatives was developed through a one-pot, three-component reaction involving acenaphthylene-1,2-dione and 1H-pyrazol-5-amine in acetic acid medium. The reaction represents the first facile conversion of acenaphthenequinone to naphthoic acid via C-C bond cleavage without need for multi-step transformation.     

ZrOCl2·8H2O mediated microwave induced [3+2] cycloaddition of azomethine ylides—a facile one-pot synthesis of novel dispiroheterocycles

An efficient microwave-assisted, ZrOCl₂·8H₂O mediated, synthesis of novel dispiro-oxindolopyrrolidines and -pyrrolizidines was accomplished through [3+2] cycloaddition reaction of azomethine ylides derived from acenaphthenequinone and sarcosine/l-proline with (E)-2-oxoindolino-3-ylidene acetophenones in good yields.     

On the Redox Reaction of 1,2-Bis(diphenylphosphino) Alkanes Toward o-, and p-Quinones

Abstract

The reaction of 1,2-bis(diphenylphosphino)ethane with substituted o-benzo-quinones afforded new bis(6-hydroxycyclohexa-2,4-dienone) derivatives. Treatment of the same reagent with o-naphthoquinone, phenanthrenequinone, and acenaphthenequinone gave the respective bis(diphenylphosphoryl)ethylidenes or diacenaphthylenone derivatives. On the other hand, p-quinones react with 1,2-bis(diphenylphosphino)methane to yield the corresponding 4-hydroxycyclohexa-2,5-dien-1-ones. Possible reaction mechanisms are considered and the structural assignments are based on compatible analytical and spectroscopic data.     

Baker''''s yeast mediated reduction of substituted acenaphthenequinones: Regio-and enantioselective preparation of mono-hydroxyacenaphthenones

Baker's yeast mediated reduction of acenaphthenequinone within 4-10 h afforded mono-hydroxyacenaphthenone mainly with low enantioselectivity, the substrate and mono-hydroxyacenaphthenone product almost converted to dihydroxyacenaphthene after 48 h. By control of the reaction time and in the presence of DMF as co-solvent, the reduction of 6-substituted acenaphthenequinones under vigorous agitation afforded the corresponding 2-hydroxyacenaphthenones in 24-84% yields with 10-93% ee.