cas 6628-97-3, 2-ANILINO-1,4-NAPHTHOQUINONE

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Copper-catalyzed one-pot amine-alkylation of quinones with amines and alkanes
A copper-catalyzed one-pot amine-alkylation of quinones with amines and alkanes in the presence of di-tert-butyl peroxide (DTBP) was developedviaa radical reaction process. Various alkanes and aromatic or aliphatic amines with diverse structures and electronic properties are suitable substrates, and the chirality of amines can be maintained for the transformation. This method has high step and atom economy for straightforward access to aminated and alkylated quinones from readily available starting materials.
Yang, Jian,Wang, Bei,Zhang, Yuankang,Zhang, Shuqing,He, Shuai,Shi, Zhi-Chuan,Wang, Ji-Yu
p. 988 - 992
(2021)
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Exploration of Benzo[b]carbazole-6,11-diones as anticancer agents: Synthesis and studies of hTopoIIα inhibition and apoptotic effects
Two series of (hetero)arylamino-naphthoquinones and benzo-fused carbazolequinones were considered for study with the rationale that related structural motifs are present in numerous drugs, clinical trial agents, natural products and hTopoIIα inhibitors. Total 42 compounds were synthesized by reactions including dehydrogenative C–N and Pd-catalyzed C–C bond forming transformations. These compounds were screened against numerous cancer cells including highly metastatic one (MCF-7, MDA-MB-231, H-357 and HEK293T), and normal cells (MCF 10A). Some of the active compounds were evaluated for clonogenic cell survival and apoptotic effects in cancer cells (DAPI nuclear staining, Comet assay, Annexin-V-FITC/PI dual staining, flow cytometry, and western blot analysis with relevant proteins). All compounds were tested for hTopoIIα inhibitory activity. The investigated series compounds showed important properties like significant apoptotic antiproliferation in cancer cells with cell cycle arrest at S-phase and downregulation of NF- κβ signaling cascade, relatively less cytotoxicity to normal cells, and hTopoIIα inhibition with more efficiency compared to an anticancer drug etoposide.
Banerjee, Uttam C.,Chaudhary, Hiteshkumar,Daniel, Divine P,Das, Biswajit,Grewal, Preeti,Guchhait, Sankar K.,Kumar, Gulshan,Kundu, Chanakya N.,Nayak, Deepika,Paul, Subarno,Sisodiya, Shailendra
supporting information

(2021/08/12)

t-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines
The transition-metal free amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines, such as various (hetero)aromatic amine and aliphatic aminevia t-BuOK-mediated oxidative coupling at room temperature has been developed. This react
Dong, Yu,Mei, Ting,Luo, Qi-Qi,Feng, Qiang,Chang, Bo,Yang, Fan,Zhou, Hong-Wei,Shi, Zhi-Chuan,Wang, Ji-Yu,He, Bing
p. 6776 - 6780
(2021/02/21)

Computer-aided design of 1,4-naphthoquinone-based inhibitors targeting cruzain and rhodesain cysteine proteases
Chagas disease and Human African Trypanosomiasis (HAT) are caused by Trypanosoma cruzi and T. brucei parasites, respectively. Cruzain (CRZ) and Rhodesain (RhD) are cysteine proteases that share 70% of identity and play vital functions in these parasites.
Cardoso, Sílvia Helena,Guimar?es, Ari Souza,McKerrow, James H.,Silva, Leandro Rocha,da Silva, Elany Barbosa,da Silva-Júnior, Edeildo Ferreira,do Nascimento, Jadiely,do Santos Nascimento, Igor José
(2021/05/21)

Photoinduced EDA Complexes Enabled Radical Tandem Cyclization/Arylation of Unactivated Alkene with 2-Amino-1,4-naphthoquinones
A visible-light-induced radical tandem cyclization/arylation between 2-amino-1, 4-naphthoquinone and N-allyl-2-bromo-2,2-difluoroacetamides has been developed without an external photocatalyst. The transformation could be carried out at room temperature a
Sun, Bin,Shi, Xiayue,Zhuang, Xiaohui,Huang, Panyi,Shi, Rongcheng,Zhu, Rui,Jin, Can
supporting information
p. 1862 - 1867
(2021/03/08)

It takes two to tango: synthesis of cytotoxic quinones containing two redox active centers with potential antitumor activity
We report the synthesis of 47 new quinone-based derivativesviaclick chemistry and their subsequent evaluation against cancer cell lines and the control L929 murine fibroblast cell line. These compounds combine two redox centers, such as anortho-quinone/para-quinone or quinones/selenium with the 1,2,3-triazole nucleus. Several of these compounds present IC50values below 0.5 μM in cancer cell lines with significantly lower cytotoxicity in the control cell line L929 and good selectivity index. Hence, our study confirms the use of a complete and very diverse range of quinone compounds with potential application against certain cancer cell lines.
Almeida, Renata G.,Barbosa, Breno P. A.,Braga, Antonio L.,Costa, Pedro M. S.,Gatto, Claudia C.,Jacob, Claus,Jardim, Guilherme A. M.,Lima, Daisy J. B.,Pereira, Cynthia L. M.,Pessoa, Claudia,Santos, Augusto C. C.,Scheide, Marcos R.,de Carvalho, Guilherme G. C.,Valen?a, Wagner O.,da Silva Júnior, Eufranio N.
supporting information
p. 1709 - 1721
(2021/11/16)

IDO inhibitor, preparation method and applications thereof
The invention relates to an IDO inhibitor, a preparation method and applications thereof, and belongs to the technical field of medicinal chemistry. The IDO inhibitor with the characteristics of a structure represented by a general formula I or the pharma
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Paragraph 0155-0158; 0321-0324

(2020/04/17)

AMINO-QUINONE ANTIPOLYMERANTS AND METHODS OF USING
Described are methods and composition for inhibiting polymerization of a monomer (e.g., styrene) composition using an aminated quinone antipolymerant, such as an aminated benzoquinone or aminated naphthoquinone antipolymerant having one or more secondary or tertiary amine group(s). The aminated quinone antipolymerant can be used with little or no nitroxyl group containing antipolymerant yet still provide excellent antipolymerant activity in a monomer-containing composition.
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Paragraph 94-95

(2020/05/12)

A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water
A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated. This method can be scaled up and we conducted further transformation of the obtained 2-(N-substituted amino)-1,4-naphthoquinones to synthesize carbazolequinone derivatives.
Chen, Xu-Ling,Dong, Yu,He, Shuai,Zhang, Rui,Zhang, Hua,Tang, Lei,Zhang, Xiao-Mei,Wang, Ji-Yu
supporting information
p. 615 - 619
(2019/03/08)

Method for synthesizing 2-substituted amino-1,4-naphthoquinone derivative
The invention discloses a method for synthesizing a 2-substituted amino-1,4-naphthoquinone derivative. The method comprises the following steps: mixing a nitro compound, 2-substituted 1,4-naphthoquinone, a catalyst, a metal and a solvent uniformly at 20-100 DEG C; adding an H source, stirring the components for reaction for 1-24h; performing a reduction-addition reaction between the nitro compoundand the 2-substituted 1,4-naphthoquinone; after the reaction, adding water to the reaction system for dilution; performing filtering; extracting filtrate with ethyl acetate; after organic phases arecombined, washing the mixture with saturated saline solution and drying the mixture with anhydrous sodium sulfate sequentially; subsequently, performing filtering, and performing vacuum concentrationto remove a solvent; and packing solids into a column, and performing separation through column chromatography (a ratio of petroleum ether to ethyl acetate is 5:1) to obtain red solids. Compared withan existing synthesis method, the synthesis method provided by the invention has a wide range of raw materials and the raw materials are easy to obtain; compared with amine compounds, nitro compoundshave better stability; and the synthesis method provided by the invention is simple to operate and mild in reaction condition.
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Paragraph 0031-0037

(2019/05/28)

Synthesis of carbazoloquinone derivatives and their antileukemic activity via modulating cellular reactive oxygen species
Carbazoloquinone alkaloids are of great interest as privileged structures for anticancer drug molecules. The purpose of this study was to investigate the structure-activity relationships of carbazoloquinone derivatives as anticancer agents. A series of ca
Suematsu, Natsumi,Ninomiya, Masayuki,Sugiyama, Hodaka,Udagawa, Taro,Tanaka,Koketsu, Mamoru
supporting information
p. 2243 - 2247
(2019/07/03)

Fluorescent 1,4-Naphthoquinones to Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains
Recent clinical approvals of brain imaging radiotracers targeting amyloid-β provided clinicians the tools to detect and confirm Alzheimer's disease pathology without autopsy or biopsy. While current imaging agents are effective in postsymptomatic Alzheimer's patients, there is much room for improvement in earlier diagnosis, hence prompting a need for new and improved amyloid imaging agents. Here we synthesized 41 novel 1,4-naphthoquinone derivatives and initially discovered 14 antiamyloidogenic compounds via in vitro amyloid-β aggregation assay; however, qualitative analyses of these compounds produced conflicting results and required further investigation. Follow-up docking and biophysical studies revealed that four of these compounds penetrate the blood-brain barrier, directly bind to amyloid-β aggregates, and enhance fluorescence properties upon interaction. These compounds specifically stain both diffuse and dense-core amyloid-β plaques in brain sections of APP/PS1 double transgenic Alzheimer's mouse models. Our findings suggest 1,4-naphthoquinones as a new scaffold for amyloid-β imaging agents for early stage Alzheimer's.
Neo Shin, Naewoo,Jeon, Hanna,Jung, Youngeun,Baek, Seungyeop,Lee, Sejin,Yoo, Hee Chan,Bae, Gi Hun,Park, Keunwan,Yang, Seung-Hoon,Han, Jung Min,Kim, Ikyon,Kim, Youngsoo
p. 3031 - 3044
(2019/05/16)

Transition metal mediated selective C vs N arylation of 2-aminonaphthoquinone and its application toward the synthesis of benzocarbazoledione
Selective C vs N-arylation of 2-aminonaphthoquinone was achieved using different transition metal salts and arylboronic acids. Mn(OAc)3·2H2O provided C-arylated product whereas NiCl2·6H2O and Cu(OAc)2
Ashok, Polu,Ilangovan, Andivelu
supporting information
p. 438 - 441
(2018/01/03)

Isomerization of 4-arylamino-1,2-naphthoquinones to 2-arylamino-1,4-naphthoquinones
4-Arylamino-1,2-naphthoquinones isomerize into 2-arylamino-1,4-naphthoquinones upon refluxing in acetic acid. The isomerization follows two routes via intermediate 2-hydroxy-1,4-naphthoquinone and 2-arylamino-1,4-naphthoquinone 4-N-arylimines.
Gornostaev,Rukovets,Lavrikova,Khalyavina, Yu. G.,Stashina
p. 1007 - 1010
(2017/10/31)

Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones
Several synthetic and natural naphthoquinone derivatives have been associated with antifungal activity. Candida albicans is a fungus that is known to exist in the normal human flora, but under certain conditions it can cause mild to fatal infections. Its pathogenicity has been associated with fungus conversion from cellular yeast to filamentous form Y–M. Inhibition of this process by several anilino-, dianilino-, phenoxy-, and diphenoxy-1,4-naphthoquinones was investigated in order to find some correlation between structure, redox properties and biological activity.
Leyva, Elisa,López, Lluvia I.,de la Cruz, Ramón F. García,Espinosa-González, Claudia G.
p. 1813 - 1827
(2017/02/15)

Synthesis of novel substituted methoxybenzo[2,3-b]carbazole derivatives via C-H functionalization. Experimental and theoretical characterization of their photophysical properties
The novel, highly blue, fluorescent N-methyl-6,11-dimethoxybenzo[2,3-b]carbazole derivatives were prepared by oxidative coupling of anilines with naphthoquinone followed by palladium catalyzed oxidative [Formula presented] functionalization and a one pot
Lisboa, Cinthia da Silva,de Lucas, Nanci C.,Garden, Simon J.
p. 618 - 632
(2016/08/23)

New family of antimicrobial agents derived from 1,4-naphthoquinone
Naphthalene-1,4-dione derivatives were synthesized and tested against selected bacterial strains. All the tested compounds were prepared by direct introduction of corresponding substituents into the naphthoquinone core in oxidative conditions. In this stu
Janeczko, Monika,Demchuk, Oleg M.,Strzelecka, Dorota,Kubiński, Konrad,Mas?yk, Maciej
p. 1019 - 1019
(2016/11/02)

2-(Fluoro-) and 2-(methoxyanilino)-1,4-naphthoquinones. Synthesis and mechanism and effect of fluorine substitution on redox reactivity and NMR
The influence of catalysts on the addition of methoxy- and fluoroanilines with 1,4-naphthoquinone to give methoxy- and fluoro-substituted 2-(anilino)-1,4-naphthoquinones was investigated. In the absence of a catalyst, this reaction requires long times and
Leyva, Elisa,Baines, Kim M.,Espinosa-González, Claudia G.,Magaldi-Lara, Diego A.,Loredo-Carrillo, Silvia E.,De Luna-Méndez, Telma A.,López, Lluvia I.
p. 152 - 160
(2015/10/12)

A one-pot, three-component reaction for the synthesis of novel 7-arylbenzo[c]acridine-5,6-diones
A one pot domino protocol for an efficient synthesis of 7-arylbenzo[c]acridine-5,6-diones, with a novel nucleus, has been developed by reacting 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and aromatic amines using environmentally benevolent p-tolue
Mahajan, Shivani,Khullar, Sadhika,Mandal, Sanjay K.,Singh, Inder Pal
supporting information
p. 10078 - 10081
(2014/08/18)

INHIBITORS OF THE MITF MOLECULAR PATHWAY
Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.
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Paragraph 00349

(2015/01/09)

2-Phenylaminonaphthoquinones and related compounds: Synthesis, trypanocidal and cytotoxic activities
A series of new 2-aminonaphthoquinones and related compounds were synthesized and evaluated in vitro as trypanocidal and cytotoxic agents. Some tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar or higher activity and selectivity as compared with current trypanocidal drug, nifurtimox. Compound 4l exhibit higher selectivity than nifurtimox against Trypanosoma cruzi in comparison with Vero cells. Some of the synthesized quinones were tested against cancer cells and normal fibroblasts, showing that certain chemical modifications on the naphthoquinone moiety induce and excellent increase the selectivity index of the cytotoxicity (4g and 10). The results presented here show that the anti-T. cruzi activity of 2-aminonaphthoquinones derivatives can be improved by the replacement of the benzene ring by a pyridine moiety. Interestingly, the presence of a chlorine atom at C-3 and a highly lipophilic alkyl group or aromatic ring are newly observed elements that should lead to the discovery of more selective cytotoxic and trypanocidal compounds.
Sieveking, Ivan,Thomas, Pablo,Estevez, Juan C.,Quinones, Natalia,Cuellar, Mauricio A.,Villena, Juan,Espinosa-Bustos, Christian,Fierro, Angelica,Tapia, Ricardo A.,Maya, Juan D.,Lopez-Munoz, Rodrigo,Cassels, Bruce K.,Estevez, Ramon J.,Salas, Cristian O.
p. 4609 - 4620
(2014/10/15)

Spectral and structural characterization of 2-(fluorophenylamino)- and 2-(nitrophenylamino)-1,4-naphthoquinone derivatives
Naphthoquinone amino derivatives exhibit interesting physicochemical properties and are of interest for potential medicinal purposes. The preparation of novel 2-(nitrophenylamino)-1,4-naphthoquinones derivatives was achieved by reaction of nitroanilines with 1,4-naphthoquinone with a catalytic amount of FeCl3 or by direct nitration of 2-(phenylamino)-1,4-naphthoquinone (PAN). Structural and photophysical properties of a series of NO2PANs and FPANs derivatives are examined using computational and spectroscopic methods. Absorbance and emission spectra are measured in a range of solvent environments to examine the impact of solvent-solute interactions. Additionally quantum calculations are used to evaluate the electronic nature of the spectral transitions and compare structures of the different PAN derivatives. The lowest energy electronic transitions have charge transfer character, and show the most sensitivity to solvent and substituents. Higher energy π- π* transitions are relatively insensitive to both factors. Computational predictions are in good agreement with the experimental spectra, and provide molecular-level insight variations amongst the different aniline-substituents.
Leyva, Elisa,Schmidtke Sobeck, Sarah J.,Loredo-Carrillo, Silvia E.,Magaldi-Lara, Diego A.
p. 1 - 7
(2014/05/06)

Development of quinone analogues as dynamin GTPase inhibitors
Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4- benzoquinone 1 as a 273 ± 106 μM inhibitor. In silico lead optimization and focused library-led synthesis resulted in the development of four discrete benzoquinone/naphthoquinone based compound libraries comprising 54 compounds in total. Sixteen analogues were more potent than lead 1, with 2,5-bis-(4-hydroxyanilino)-1,4-benzoquinone (45) and 2,5-bis(4-carboxyanilino)- 1,4-benzoquinone (49) the most active with IC50 values of 11.1 ± 3.6 and 10.6 ± 1.6 μM respectively. Molecular modelling suggested a number of hydrogen bonding and hydrophobic interactions were involved in stabilization of 49 within the dynI GTP binding site. Six of the most active inhibitors were evaluated for potential inhibition of clathrin-mediated endocytosis (CME). Quinone 45 was the most effective CME inhibitor with an IC50(CME) of 36 ± 16 μM.
Macgregor, Kylie A.,Abdel-Hamid, Mohammed K.,Odell, Luke R.,Chau, Ngoc,Whiting, Ainslie,Robinson, Phillip J.,McCluskey, Adam
p. 191 - 206
(2014/08/18)

Bodipy derivatives as organic triplet photosensitizers for aerobic photoorganocatalytic oxidative coupling of amines and photooxidation of dihydroxylnaphthalenes
We used iodo-Bodipy derivatives that show strong absorption of visible light and long-lived triplet excited states as organic catalysts for photoredox catalytic organic reactions. Conventionally most of the photocatalysts are based on the off-the-shelf compounds, usually showing weak absorption in the visible region and short triplet excited state lifetimes. Herein, the organic catalysts are used for two photocatalyzed reactions mediated by singlet oxygen ( 1O2), that is, the aerobic oxidative coupling of amines and the photooxidation of dihydroxylnaphthalenes, which is coupled to the subsequent addition of amines to the naphthoquinones, via C-H functionalization of 1,4-naphthoquinone, to produce N-aryl-2-amino-1,4-naphthoquinones (one-pot reaction), which are anticancer and antibiotic reagents. The photoreactions were substantially accelerated with these new iodo-Bodipy organic photocatalysts compared to that catalyzed with the conventional Ru(II)/Ir(III) complexes, which show weak absorption in the visible region and short-lived triplet excited states. Our results will inspire the design and application of new organic triplet photosensitizers that show strong absorption of visible light and long-lived triplet excited state and the application of these catalysts in photoredox catalytic organic reactions.
Huang, Ling,Zhao, Jianzhang,Guo, Song,Zhang, Caishun,Ma, Jie
p. 5627 - 5637
(2013/07/25)

An expedient synthesis of 1,2-dihydrobenzo[g]quinoline-5,10-diones via copper(II) triflate-catalyzed intramolecular cyclization of N- propargylaminonaphthoquinones
An expedient synthesis of a series of 1,2-dihydrobenzo[g]quinoline-5,10- diones in good yields has been accomplished via three-component one pot sequential reactions of 2-hydroxynaphthalene-1,4-dione, substituted anilines and propargyl as well as 3-ethylp
Devi Bala, Balasubramanian,Muthusaravanan, Sivasubramanian,Perumal, Subbu
supporting information
p. 3735 - 3739
(2013/07/05)

Bifunctionalisation of 1,4-naphthoquinone by the oxidative addition of an alkylamine and iodine
Novel 2-iodo-3-(alkylamino) naphthalene-1,4-diones are formed in 33-70% yield by the reaction of alkylamine and 1, 4-naphthoquinone in the presence of iodine.
Huang, Huan-Ming,Li, Yu-Jin,Dai, Yin-Ping,Yu, Wu-Bin,Ye, Qin,Gao, Jian-Rong
p. 34 - 37
(2013/04/11)

Structure-activity relationship study of vitamin K derivatives yields highly potent neuroprotective agents
Historically known for its role in blood coagulation and bone formation, vitamin K (VK) has begun to emerge as an important nutrient for brain function. While VK involvement in the brain has not been fully explored, it is well-known that oxidative stress plays a critical role in neurodegenerative diseases. It was recently reported that VK protects neurons and oligodendrocytes from oxidative injury and rescues Drosophila from mitochondrial defects associated with Parkinson's disease. In this study, we take a chemical approach to define the optimal and minimum pharmacophore responsible for the neuroprotective effects of VK. In doing so, we have developed a series of potent VK analogues with favorable drug characteristics that provide full protection at nanomolar concentrations in a well-defined model of neuronal oxidative stress. Additionally, we have characterized key cellular responses and biomarkers consistent with the compounds' ability to rescue cells from oxidative stress induced cell death.
Josey, Benjamin J.,Inks, Elizabeth S.,Wen, Xuejun,Chou, C. James
p. 1007 - 1022
(2013/03/28)

Synthesis, antibacterial and antifungal activity of 2-amino-1,4- naphthoquinones using silica-supported perchloric acid (HClO4- SiO2) as a mild, recyclable and highly efficient heterogeneous catalyst
Perchloric acid adsorbed on silica gel (1 mol%) has been found to be an efficient and recyclable heterogeneous catalyst for rapid conjugate addition of primary and secondary amines with 1,4-naphthoquinone to afford 2-amino-1,4-naphthoquinones under ultrasonication in moderate to high yields without using any solvent. The compounds tested for in vitro antimicrobial activity have shown high antibacterial activity against Gram positive bacteria Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus as compared to Gram negative bacteria Burkholderia cepacia, Escherichia coli, Enterobacter cloacae, Klebseilla pneumoniae and Pseudomonas aeruginosa. High antifungal activity has been observed against Candida albicans and Issatchenkia orientalis for all the compounds.
Sharma, Upendra,Katoch, Deepali,Sood, Swati,Kumar, Neeraj,Singh, Bikram,Thakur, Archana,Gulati, Arvind
p. 1431 - 1440
(2014/01/06)

Anticancer activity and SAR studies of substituted 1,4-naphthoquinones
In this paper, we report the structure-activity relationship studies of substituted 1,4-naphthoquinones for its anticancer properties. 1,4-Naphthoquinone, Juglone, Menadione, Plumbagin and LLL12.1 were used as lead molecules to design PD compounds. Most o
Bhasin, Deepak,Chettiar, Somsundaram N.,Etter, Jonathan P.,Mok, May,Li, Pui-Kai
p. 4662 - 4669
(2013/07/26)

Efficient access to naphthoquinon-1,3-dithioles: Formal cycloaddition and oxidation of quinones and amines with CS2
An efficient strategy for one-pot synthesis of a variety of naphthoquinon-1,3-dithiole derivatives has been developed. The combined action of the formal cycloaddition and oxidation reaction of quinones and amines in the presence of CS2 without additional oxidant produced naphthoquinon-1,3-dithiole derivatives in good yields.
Huang, Huan-Ming,Li, Yu-Jin,Yang, Jian-Rong,Jia, Jian-Hong,Ye, Qing,Han, Liang,Gao, Jian-Rong
supporting information
p. 5221 - 5226
(2013/06/27)

C-H functionalization of 1,4-naphthoquinone by oxidative coupling with anilines in the presence of a catalytic quantity of copper(II) acetate
The oxidative addition of anilines (2) with 1,4-naphthoquinone (3) to give N-aryl-2-amino-1,4-naphthoquinones (1) was found to be catalyzed by copper(II) acetate. In the absence of the catalyst, the reactions are slower and give lower yields with the formation of many colateral products. In the presence of 10 mol % hydrated copper(II) acetate, the reactions are generally more efficient in that they are cleaner, higher yielding, and faster.
Lisboa, Cinthia Da S.,Santos, Vanessa G.,Vaz, Boniek G.,De Lucas, Nanci C.,Eberlin, Marcos N.,Garden, Simon J.
supporting information; experimental part
p. 5264 - 5273
(2011/08/04)

Synthesis, spectral and electrochemical characterization of novel 2-(fluoroanilino)-1,4-naphthoquinones
The preparation of novel 2-(fluoroanilino)-1,4-naphthoquinones is presented. It takes place under mild conditions by reacting the corresponding fluoroaniline and 1,4-naphthoquinone in the presence of a Lewis acid catalyst with strong oxidation properties
Leyva, Elisa,López, Lluvia I.,Loredo-Carrillo, Silvia E.,Rodríguez-Kessler, Margarita,Montes-Rojas, Antonio
experimental part
p. 94 - 101
(2011/03/22)

Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents
Several members of the phenylamino-1,4-naphthoquinone series were prepared in order to investigate structure-activity relationships (SAR) and to explore the antitumor effects associated with this scaffold. The cytotoxic effects of the aminoquinones (ECsu
Benites, Julio,Valderrama, Jaime A.,Bettega, Karina,Pedrosa, Rozangela Curi,Calderon, Pedro Buc,Verrax, Julien
experimental part
p. 6052 - 6057
(2011/01/13)

Gold(III)-catalyzed 1,4-nucleophilic addition: Facile approach to prepare 2-amino-1,4-naphthalenedione and 6-amino-5,8-quinolinedione derivatives
An efficient approach is developed to prepare different 2-amino-1,4-naphthalenedione and 6-amino-5,8-quinolinedione derivatives regioselectively by Au(III)-catalyzed 1,4-nucleophilic addition and subsequent oxidation. A wide variety of primary, secondary, and aromatic amines, as well as allylamine and 2-butynylamine are well tolerated under the mild conditions to give products in moderate to good yields. Georg Thieme Verlag Stuttgart.
Jiang, Chunhui,Wang, Shaozhong
experimental part
p. 1099 - 1102
(2009/10/14)

General method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones (X = ferrocenyl, OMe, Me, I, Cl, and NO2) from 2-methoxy-1,4-naphthoquinone and investigation of H+ and Mg2+ catalysts with DFT calculations
A rapid and simple method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones from 2-methoxy-1,4-naphthoquinone, in boiling MeOH, using MgCl2 and p-toluenesulfonic acid as catalysts is described. This methodology has been applied successfully to the synthesis of electron donor (4-OMe, 4-Me, 4-ferrocenyl) and electron withdrawing (4-I, 4-Cl, 4- and 3-NO2) aniline derivatives. The effect of both H+ and Mg2+ as catalysts was investigated using DFT calculations carried out at the B3LYP/6-31G(d) level. The electronic properties of the novel 2-(4-ferrocenylphenylene)amine-1,4-naphthoquinone 3b were investigated and show that the ferrocenyl and the methoxy group have similar electron donor properties in 2-(4-methoxy)amine-1,4-naphthoquinone 3a.
Francisco, Acácio I.,Vargas, Maria D.,Carneiro, J. Walkimar de M.,Lanznaster, Maurício,Torres, José C.,Camara, Celso A.,Pinto, Angelo C.
experimental part
p. 228 - 232
(2009/04/13)

Green protocol for conjugate addition of amines to p-quinones accelerated by water
Amines undergo smooth conjugate addition to p-quinones in H2O at ambient temperature in the absence of a catalyst to produce 2-aminoquinones in excellent yields. Significant rate acceleration of this reaction is observed in H2O compa
Yadav, Jhillu S.,Reddy, Basi V. Subba,Swamy, Tallapally,Shankar, Kattela Shiva
experimental part
p. 1317 - 1320
(2009/12/04)

Facile synthesis of 2-amino-1,4-naphthoquinones catalyzed by molecular iodine under ultrasonic irradiation
The conjugate addition reactions of amines with 1,4-naphthoquinone were catalyzed efficiently by molecular iodine under ultrasonic irradiation to afford 2-amino-1,4-naphthoquinones in moderate to excellent yields. Copyright Taylor & Francis Group, LLC.
Liu, Bing,Ji, Shun-Jun
p. 1201 - 1211
(2008/09/18)

Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air: Reaction development and scope
(Figure Presented) New reaction conditions for intramolecular palladium(II)-catalyzed oxidative carbon-carbon bond formation under air are described. The use of pivalic acid as the reaction solvent, instead of acetic acid, results in greater reproducibility, higher yields, and broader scope. This includes the use of electron-rich diarylamines as illustrated in the synthesis of three naturally occurring carbazole products: Murrayafoline A, Mukonine, and Clausenine. A variety of side products have also been isolated, casting light on competing reaction pathways and revealing new reactivity with palladium(II) catalysis.
Liegault, Benoit,Lee, Doris,Huestis, Malcolm P.,Stuart, David R.,Fagnou, Keith
p. 5022 - 5028
(2008/09/21)

[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium/1, 1′-bis(diphenylphosphino)ferrocene catalyzed synthesis of 2,3-diamino-1,4-naphthoquinones
A general method for the synthesis of 2,3-diamino-1,4-naphthoquinone derivatives via the palladium-catalyzed coupling of 2-amino-3-chloro-1,4- naphthoquinones with amines is described. The scope and limitations of the coupling process using [1,1′-bis(diph
Xiao, Lei Wang,Xiu, Fang Zheng,Wang, Lei,Reiner, John,Wei, Lin Xie,Jun, Biao Chang
p. 989 - 998
(2008/02/02)

Structure-activity delineation of quinones related to the biologically active Calothrixin B
Quinones such as Calothrixins A and B display a range of biological properties. As part of our ongoing studies to elucidate the mechanism of action of the Calothrixins, several related quinones were synthesized and tested for biological activity. The resu
Bernardo, Paul H.,Chai, Christina L.L.,Guen, Maurice Le,Smith, Geoffrey D.,Waring, Paul
p. 82 - 85
(2007/10/03)

Sulfur-containing derivatives of 1,4-naphthoquinone, part 1: Disulfide synthesis
Bisulfides of 1,4-naphthoquinone were synthesized, and different methods of their synthesis were investigated. High yields and purity of disulfides were obtained from the oxidation of thiol derivatives. The latter were prepared in high yields and purity from isothiuronic salts. The obtained disulfides are synthones for compounds with a wide spectrum of biological activity.
Stasevych, Maryna V.,Plotnikov, Maxym Yu.,Platonov, Mykola O.,Sabat, Svitlana I.,Musyanovych, Rostyslav Ya.,Novikov, Volodymyr P.
p. 205 - 211
(2007/10/03)

6-Arylamino-5,8-quinolinediones and 7-arylamino-5,8-isoquinolinediones as inhibitors of endothelium-dependent vasorelaxation
6-Arylamino-5,8-quinolinediones 3 and 7-arylamino-5,8-isoquinolinediones 4 were synthesized as inhibitors of endothelium-dependent vasorelaxation. The quinones inhibited the vasorelaxation of rat aorta with the endothelium. Among them, the quinones 3a, 3b
Ryu, Chung-Kyu,Jung, Sung-Hee,Lee, Joung-Ah,Kim, Hwa-Jung,Lee, Soo-Hwan,Chung, Jin-Ho
p. 2469 - 2472
(2007/10/03)

Nitroxide Radicals. Part 21. Spontaneous Decomposition of N-Aryl 1- and 2-Naphthyl Nitroxides
N-Aryl 1-naphthyl nitroxides self-react in solution to give the corresponding secondary amines and N-aryl-1,4-naphthoquinone imines.When reaction at the 4-naphthyl position is hindered by substituents benzoquinone imines are also produced.N-Phenyl 2-naphthyl nitroxide under similar conditions gives the corresponding amine and 2-phenylamino-1,4-naphthoquinone via a 1,2-naphthoquinone imine N-oxide intermediate.
Forrester, Alexander R.,Fullerton, Joseph D.,McConnachie, Gordon
p. 1759 - 1764
(2007/10/02)

Reactivity and Structure of N-Phenyl-1-naphthylamines and Related Compounds. Part 3. Reaction with Oxygen-centred Radicals
Comparison is made between products obtained by oxidation of N-phenyl-1-naphthylamines and 1-naphthyl phenyl nitroxides with peroxyl radicals.It is concluded that oxidation of the amines does not proceed to a considerable extent via the nitroxides.Comparison is also made of products obtained from these amines and nitroxides by oxidation with Fremy's salt.
Forrester, Alexander R.,Fullerton, Joseph D.,McConnachie, Gordon
p. 2711 - 2715
(2007/10/02)

Quinone Chemistry. Reaction of 2,3-Dichloro-1,4-naphthoquinone with Arylamines in Pyridine
2,3-Dichloro-1,4-naphthoquinone (1) reacts with arylamines (2) in pyridine to afford 2-(arylamino)-3-chloro-1,4-naphthoquinone (6), 2-(arylamino)-1,4-naphthoquinone (5), 2-(arylamino)-1,4-naphthoquinone-3-pyridinium perchlorate (4), and 2-amino-1,4-naphth
Agarwal, Nand L.,Schaefer, Wolfram
p. 5139 - 5143
(2007/10/02)