- An expeditious and green one-pot synthesis of 12-substituted-3,3-dimethyl-3,4,5,12-tetrahydrobenzo[b]acridine-1,6,11(2H)-triones
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In this study, several new 12-aryl/heteroaryl-3,3-dimethyl-tetrahydrobenzo[b]acridine-1,6,11(2H)-trione heterocyclic compounds that can be considered as 1,4-naphthoquinone fused with 4-substituted 7,7-dimethyl-4,6,7,8-tetrahydroquinolin-5(1H)-ones, have been synthesized through the three-component cyclocondensation of benzaldehydes/heteroaldehydes, 2-amino-1,4-naphthoquinone, and dimedone. The pot-, atom-, and step-economy reactions were implemented under reflux conditions. One of the most important aspects of this reaction is the use of ethanol as the reaction medium taking into account the principles of green chemistry. Not using a catalyst in this type of reactions is also significant from the standpoint of green chemistry. The protocol developed in this study has the benefits of the simplicity, no use of chromatographic methods for purification, structural diversity, employing non-toxic solvent, good-to-high yields, safety, and using cost-effective solvent. The structures of the newly synthesized 1,4-naphthoquinone fused with 4-substituted 7,7-dimethyl-4,6,7,8-tetrahydroquinolin-5(1H)-ones were confirmed employing spectroscopic data as well as elemental analysis.
- Kamalifar, Saiedeh,Kiyani, Hamzeh
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Read Online
- Amination of Naphthoquinones with Azidotrimethylsilane
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A new method for the synthesis of aminonaphthoquinones from 1,2- or 1,4-naphthoquinones and azidotrimethylsilane is described.In a similar manner 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone was transformed into 2-amino-3-hydroxy-1,4-naphthoquinone.The mechanism of these transformations and the formation of by-products are discussed. - Keywords: Amination with direct amino group introduction; Aminonaphthoquinones
- Husu, Breda,Kafka, Stanislav,Kadunc, Zdenka,Tisler, Miha
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- Reaction of hydroxylamines with 1,4-quinones: A new direct synthesis of aminoquinones
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A novel one-step amination of 1,4-naphthoquinones and 1,4-benzoquinones is described. O-Benzylhydroxylamine was found to be the best aminating agent while O-methylhydroxylamine, carboxymethoxylamine and free hydroxylamine are less effective.
- Bittner,Lempert
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Read Online
- Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- And Alkynylnaphthoquinones and Derivatives
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Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free Cu I -mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.
- Demidoff, Felipe C.,Rodrigues Filho, Eduardo José P.,De Souza, Andréa Luzia F.,Netto, Chaquip D.,De Carvalho, Leandro L.
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supporting information
p. 4097 - 4109
(2021/08/31)
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- Benzoquinoxalinone compound as well as synthesis method and application thereof
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The invention discloses a series of benzoquinoxalinone compounds as well as a synthesis method and application thereof, in particular to compounds of formula (I) as well as synthesis method and application thereof in treating cancer
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Paragraph 0105-0106
(2021/11/10)
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- The one-pot synthesis of amidonapthoquinones from aminonaphthoquinones
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Described here is a one-pot method of synthesizing amidonaphthoquinones from the corresponding aminonaphthoquinones. The scope of amides that can be synthesized using this methodology is relatively broad and the yield of product is higher than the traditional methods of synthesizing these substrates. 2009 Elsevier Ltd. All rights reserved.
- Rainier, Jon D.,Yin, Jinya
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- P2X7 receptor inhibition by 2-amino-3-aryl-1,4-naphthoquinones
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Extracellular ATP activates purinergic receptors such as P2X7, cationic channels for Ca2+, K+, and Na+. There is robust evidence of the involvement of these receptors in the immune response, so P2X7 receptors (P2X7R) are considered a potential therapeutic target for the development of anti-inflammatory drugs. Although there are many studies of the anti-inflammatory properties of naphthoquinones, these molecules have not yet been explored as P2X7 antagonists. In previous work, our group prepared 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones and studied their action on P2X7R. In this paper, eight 2-amino-3-aryl-1,4-naphthoquinones were evaluated to identify the inhibitory activity on P2X7R and the toxicological profile. Three analogues (AD-4CN, AD-4Me, and AD-4F) exhibited reduced toxicity for mammalian cells with CC50 values higher than 500 μM. These three 3-substituted 2-amino-1,4-naphthoquinones inhibited murine P2X7R (mP2X7R) in vitro. However, the analogues AD-4CN and AD-4Me showed low selectivity index values. AD-4F inhibited both mP2X7R and human P2X7R (hP2X7R) with IC50 values of 0.123 and 0.93 μM, respectively. Additionally, this analogue exhibited higher potency than BBG at inhibiting the ATP-induced release of IL-1β in vitro. Carrageenan-induced paw edema in vivo was reversed for AD-4F with an ID50 value of 11.51 ng/kg. Although AD-4F was less potent than previous 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones such as AN-04 in vitro, this 3-substituted 2-amino-1,4-naphthoquinone revealed higher potency in vivo to reduce the edematogenic response. In silico analysis suggests that the binding site of the novel 2-amino-3-aryl-1,4-naphthoquinone derivatives, including all the tautomeric forms, is located in the pore area of the hP2X7R model. Based on these results, we considered AD-4F to be a satisfactory P2X7R inhibitor. AD-4F might be used as a scaffold structure to design a novel series of inhibitors with potential inhibitory activity on murine (mP2X7R) and human (hP2X7R) P2X7 receptors.
- de Luna Martins, Daniela,Borges, Adriel Alves,e Silva, Nayane A. do A.,Faria, Juliana Vieira,Hoelz, Lucas Villas B?as,de Souza, Hellen Valério Chaves Moura,Bello, Murilo Lamim,Boechat, Nubia,Ferreira, Vitor Francisco,Faria, Robson Xavier
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supporting information
(2020/10/06)
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- Ruthenium(II)-Catalyzed Double Annulation of Quinones: Step-Economical Access to Valuable Bioactive Compounds
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Double ruthenium(II)-catalyzed alkyne annulations of quinones were accomplished. Thus, a strategy is reported that provides step-economical access to valuable quinones with a wide range of applications. C?H/N?H activations for alkyne annulations of naphthoquinones provided challenging polycyclic quinoidal compounds by forming four new bonds in one step. The singular power of the thus-obtained compounds was reflected by their antileukemic activity.
- da Silva Júnior, Eufranio N.,de Carvalho, Renato L.,Almeida, Renata G.,Rosa, Luisa G.,Fantuzzi, Felipe,Rogge, Torben,Costa, Pedro M. S.,Pessoa, Claudia,Jacob, Claus,Ackermann, Lutz
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supporting information
p. 10981 - 10986
(2020/07/13)
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- A novel approach to oxazole-containing diterpenoid synthesis from plant roots: Salviamines e and F
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In this study, salviamines E and F, which are structurally unique abietane-type diterpene alkaloids containing an oxazole ring, were efficiently synthesized from a known molecule, 5,7,8-trimethoxy-1-naphthol. The synthetic sequence involves the following crucial steps: (i) the assembly of a carbon skeleton by coupling a six-carbon homoprenyl unit with a naphthalene moiety (Kumada-Tamao-Corriu coupling); (ii) the construction of a tricyclic phenanthrene ring by acid-induced cyclization of a naphthalene derivative with a homoprenyl side chain; (iii) the formation of an oxazole ring by nucleophilic ring closure of a 2-aminophenylene-1,4-diyl-diformate or -diacetate moiety and (iv) Friedel-Crafts acetylation at the C13 position of the tetracyclic intermediates to obtain the two target molecules, salviamines E and F. To the best of our knowledge, salviamine synthesis is reported here for the first time.
- Narita, Koichi,Fujisaki, Narumi,Sakuma, Yuta,Katoh, Tadashi
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p. 655 - 663
(2019/01/24)
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- Synthetic method for NSC128981
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The invention discloses a synthetic method for NSC128981. The structure of NSC128981 is as shown in a formula (I). The synthetic method comprises the following steps: subjecting naphthoquinone (II) toan amination reaction to obtain 2-amino-1,4-naphthoquinone (III); subjecting 2-mino-1,4-naphthoquinone (III) to p-chlorophenylthiolation to obtain 2-amino-3-p-chlorophenylthio-1,4-naphthoquinone (IV); and adding an acetylation agent into 2-amino-3-p-chlorophenylthio-1,4-naphthoquinone (IV) under acidic conditions for an acetylation reaction so as to obtain NSC128981 (I). A reaction formula is asdescribed in the specification. The method of the invention has the advantages of simple steps, low price and easy availability of raw materials, high yield, high product purity, low cost and the like, and avoids the use of toxic or corrosive chlorination reagents in the prior art.
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Paragraph 0029-0032
(2019/11/13)
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- One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones
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Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency,mild conditions, and benign functional group compatibilitywas reported. Avariety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.
- Yuan, Jiaqi,He, Qian,Song, Shanshan,Zhang, Xiaofei,Miao, Zehong,Yang, Chunhao
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supporting information
(2019/08/30)
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- in situ Formation of RSCl/ArSeCl and Their Oxidative Coupling with Enaminone Derivatives Under Transition-metal Free Conditions
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The reaction of diorganyl disulfides or diselenides with PhICl2 in DMF at room temperature led to the in situ formation of the reactive organosulfenyl chloride (RSCl) or selenenyl chloride (ArSeCl), which reacted with enaminone compounds to afford a series of α-thioenaminones or α-selenylenaminones, respectively, including the bioactive inhibitor for Cdc25B and its analogue, via the intermolecular oxidative C(sp2)-S/Se cross coupling reactions under metal-free conditions. (Figure presented.).
- Shang, Zhenhua,Chen, Qingyu,Xing, Linlin,Zhang, Yilin,Wait, Laura,Du, Yunfei
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p. 4926 - 4932
(2019/11/03)
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- Synthesis and antimicrobial evaluation of amino sugar-based naphthoquinones and isoquinoline-5,8-diones and their halogenated compounds
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Antibiotic resistance has emerged as a serious global public health problem and lately very few antibiotics have been discovered and introduced into clinical practice. Therefore, there is an urgent need for the development of antibacterial compounds with new mechanism of action, especially those capable of evading known resistance mechanisms. In this work two series of glycoconjugate and non-glycoconjugate amino compounds derived from of isoquinoline-5,8-dione and 1,4-naphthoquinone and their halogenated derivatives were synthesized and evaluated for antimicrobial activity against Gram-positive (Enterococcus faecalis ATCC 29212, Staphylococcus aureus ATCC 25923, S. epidermidis ATCC 12228, S. simulans ATCC 27851) and Gram-negative bacteria (E. coli ATCC 25922, Proteus mirabilis ATCC 15290, K. pneumoniae ATCC 4352 and P. aeruginosa ATCC 27853) strains of clinical importance. This study revealed that glycoconjugate compounds derived from halogeno-substituted naphthoquinones were more active against Gram-negative strains, which cause infections whose treatment is even more difficult, according to the literature. These molecules were also more active than isoquinoline-5,8-dione analogues with minimum inhibitory concentration (MIC = 4–32 μg/mL) within Clinical and Laboratory Standard Institute MIC values (CLSI 0.08–256 μg/mL). Interestingly the minimal bactericidal concentration (MBC) values of the most active compounds were equal to MIC classifying them as bactericidal agents against Gram-negative bacteria. Sixteen compounds among eighteen carbohydrate-based naphthoquinones tested showed no hemolytic effects on health human erythrocytes whereas more susceptibility to hemolytic cleavage was observed when using non-glycoconjugate amino compounds. In silico Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) evaluation also pointed out that these compounds are potential for oral administration with low side effects. In general, this study indicated that these compounds should be exploited in the search for a leading substance in a project aimed at obtaining new antimicrobials more effective against Gram-negative bacteria.
- Dias, Flaviana R.F.,Novais, Juliana S.,Devillart, Talita A. do Nascimento Santos,da Silva, Wanderson Amaral,Ferreira, Matheus O.,Loureiro, Raquel de S.,Campos, Vinícius R.,Ferreira, Vitor F.,de Souza, Maria C.B.V.,Castro, Helena C.,Cunha, Anna C.
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- Highly Efficient Synthesis and Structure–Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones
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A platform of highly efficient synthetic methodologies has been established to access a focused library of substituted 1,4-naphthoquinones derivatives functionalized with a diversity of amino/hydroxy/alkyl groups. Furthermore, the structure–activity relationship deduced from antiproliferative activities and toxicities of this 1,4-naphthoquinone library and intracellular reactive oxygen species (ROS) level detections might warrant future potential of plumbagin (2) and compound 13 as promising basic structures to develop novel anti-cancer agents.
- Bao, Na,Ou, Jinfeng,Shi, Wei,Li, Na,Chen, Li,Sun, Jianbo
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supporting information
p. 2254 - 2258
(2018/06/04)
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- Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents
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Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.
- Acu?a, Julio,Piermattey, Jhoan,Caro, Daneiva,Bannwitz, Sven,Barrios, Luis,López, Jairo,Ocampo, Yanet,Vivas-Reyes, Ricardo,Aristizábal, Fabio,Gaitán, Ricardo,Müller, Klaus,Franco, Luis
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- Metal-free, base promoted sp2 C-H functionalization in the sulfonamidation of 1,4-naphthoquinones
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A novel, metal-free, base promoted sp2 C-H functionalization in the sulfonamidation of 1,4-naphthoquinones via a [3 + 2] cycloaddition reaction using sulfonyl azides under mild reaction conditions is reported. In this straightforward atom- and step-economical protocol, the active alkene moiety of quinone undergoes a thermal azide-alkene [3 + 2] cycloaddition followed by proton abstraction, ring opening and elimination of a nitrogen molecule to form sulfonamidation products in good yield and all the synthesized sulfonamidation derivatives exhibit good absorption and emission characteristics. In addition, the electrochemical properties of both 1,4-naphthoquinone and menadione sulfonamidation derivatives are studied and significant redox potentials are observed. Other important features of this methodology are readily accessible and easy to handle starting materials, milder conditions, reaction with a wide range of substrates and shorter reaction times with good yields.
- Devenderan, Ramanathan,Kasi, Pitchumani
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supporting information
p. 5294 - 5300
(2018/08/03)
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- Novel naphtho[2,1-d]oxazole-4,5-diones as NQO1 substrates with improved aqueous solubility: Design, synthesis, and in vivo antitumor evaluation
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A new series of ortho-naphthoquinone analogs of β-lapachone were designed, synthesized and evaluated. The biological results indicated that most of our compounds were efficient substrates for NQO1. The new scaffold with water-soluble side chain resulted in greater solubility under acidic condition compared to β-lapachone. Thus avoiding the use of hydroxylpropyl β-cyclodextrin which would finally cause the rapid drug clearance from the blood and dose-limiting toxicity in the form of hemolytic anemia. The most soluble and promising compound in this series was 2-((4-benzylpiperazin-1-yl)methyl)naphtho[2,1-d]oxazole-4,5-dione (3k), which inhibited cancer cell (NQO1-rich A549 cell line) growth at IC50 values of 4.6 ± 1.0 μmol·L-1. Furthermore, compound 3k had in vivo antitumor activity in an A549 tumor xenografts mouse model comparable to the activity obtained with β-lapachone. The results indicated that these ortho-naphthoquinones could serve as promising leads for further optimization as novel substrates for NQO1.
- Li, Xiang,Bian, Jinlei,Wang, Nan,Qian, Xue,Gu, Jing,Mu, Tong,Fan, Jun,Yang, Xiuwen,Li, Shangzhen,Yang, Tingting,Sun, Haopeng,You, Qidong,Zhang, Xiaojin
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p. 1006 - 1013
(2016/02/19)
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- Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: Scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C
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A novel etherification of 2-hydroxy-1,4-naphthoquinone derivatives with alkoxyalkyl chlorides and hydride bases is described. Precise study of the conditions and substrate scope suggested that the reaction occurs specifically in the molecule having a 2-hydroxy-1,4-benzoquinone skeleton. A chemoselective O-methylation reaction was achieved to afford a synthetically important intermediate, which offered easy access to a natural product possessing anti-tumor activity.
- Ogata, Tokutaro,Yoshida, Tomoyo,Shimizu, Maki,Tanaka, Manami,Fukuhara, Chie,Ishii, Junko,Nishiuchi, Arisa,Inamoto, Kiyofumi,Kimachi, Tetsutaro
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p. 1423 - 1432
(2017/02/15)
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- 1,2-Naphthoquinone-based Derivatives and and Methods for Preparing them
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The present invention relates to a compound represented by chemical formula (1), a pharmaceutically acceptable salt, a hydrate, a solvate, a prodrug, a tautomer, an enantiomer, or a pharmaceutically acceptable diastereomer thereof, a preparing method thereof, and a medical composition having a treating or preventing effect of metabolic diseases containing the same. Here, R_1 to R_3, and X_1 to X_6 are the same as defined in a first claim.COPYRIGHT KIPO 2015
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Paragraph 0197-0201
(2016/11/24)
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- COMPOSITIONS AND METHODS FOR TREATING NEUROLOGICAL DISEASES OR INJURY
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Provided are compounds for the treatment of neurological diseases or injuries, including neurodegenerative diseases, stroke, trauma, epilepsy, acute and chronic kidney injuries, diabetes mellitus, and/or seizures. In some embodiments, derivatives of vitamin K are provided.
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Paragraph 00208
(2014/05/24)
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- INHIBITORS OF THE MITF MOLECULAR PATHWAY
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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 00347
(2015/01/09)
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- Synthesis of 2-amino(alkylamino)-3-nitro-1,4-naphthoquinones
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The reaction of 2-amino(alkylamino)-1,4-naphthoquinones with nitrating mixture in concentrated sulfuric acid leads to the formation of 2-amino(alkylamino)-3-nitro-1,4-naphthoquinones.
- Gornostaev,Kryukovskaya,Lavrikova,Vigant,Gatilov, Yu. V.
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p. 205 - 210
(2014/04/17)
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- Structure-activity relationship study of vitamin K derivatives yields highly potent neuroprotective agents
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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
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p. 1007 - 1022
(2013/03/28)
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- Synthesis using microwave irradiation and antibacterial evaluation of new N,O-acetals and N,S-acetals derived from 2-amino-1,4-naphthoquinones
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This paper describes a novel series of N,O-acetals and N,S-acetals (7a-o) derived from 2-amino-1,4-naphthoquinones that were synthesized and evaluated as potential antimicrobial agents. These compounds were obtained in good yields using microwave irradiation, and several of them showed promising antibacterial profiles. Three of our biologically active 2-amino-1,4-naphthoquinone N,O-acetals and N,S-acetals tested against hospital bacterial strains were identified as potential lead compounds. Characterization of all compounds was performed using one-dimensional NMR techniques (1H, 13C-APT), IR spectra, elemental analyses and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS).
- Jord?o, Alessandro K.,Novais, Juliana,Leal, Bruno,Escobar, Ana C.,Dos Santos Júnior, Helvécio M.,Castro, Helena C.,Ferreira, Vitor F.
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p. 196 - 201
(2013/07/27)
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- Synthesis of 2-(1H-1,2,3-triazol-1-yl)-1,4-naphthoquinones from 2-azido-1,4-naphthoquinone and terminal alkynes
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A series of 2-[(4-substituted 1H-1,2,3-triazol-1-yl)-1,4-naphthoquinones were prepared in moderate-to-good yields (51-90%) by the reaction of 2-azido-1,4-naphthoquinone with terminal alkynes in the presence of a catalytic amounts of copper(I) iodide in acetonitrile. Georg Thieme Verlag Stuttgart · New York.
- Do Nascimento, Wilson Silva,Camara, Celso Amorim,De Oliveira, Ronaldo Nascimento
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scheme or table
p. 3220 - 3224
(2011/11/30)
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- One-pot synthesis of 1- and 2-substituted naphtho[2,3-d][1,2,3]triazole-4, 9-diones
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(Chemical Equation Presented) A one-pot three-component [2+3] cycloaddition for the synthesis of 1-alkyl 1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione and 2-alkyl 2H-naphtho[2,3-d][1,2,3]triazole-4,9-dione has been developed. By taking the advantage of diffe
- Zhang, Jianjun,Chang, Cheng-Wei Tom
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experimental part
p. 4414 - 4417
(2009/09/06)
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- Efficient Synthesis of Aminonaphthoquinones and Azidobenzohydroquinones: Mechanistic Considerations of the Reaction of Hydrazoic Acid with Quinones. An Overview
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Parameters useful to predict and control the reaction outcome of conjugate addition of hydrazoic acid to quinones have been studied, and the optimum conditions for the efficient synthesis of aminonaphthoquinones and azidobenzohydroquinones are reported. The application of this reaction for the efficient formal synthesis of dephostatin is also presented.
- Couladouros, Elias A.,Plyta, Zoi F.,Haroutounian, Serkos A.,Papageorgiou, Vassilios P.
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- 3-Aryliodonio-1,4-naphthoquinone-2-imides: A new class of aryliodonium 1,4 dipoles
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The synthesis of a new class of zwitterionic aryliodonium compounds from 2-amino-1,4-naphthoquinone and [(hydroxy)(tosyloxy)iodo]arenes is described. These dipoles exhibit an interesting reactivity under thermal and photochemical conditions.
- Papoutsis, Ioannis,Spyroudis, Spyros,Varvoglis, Anastasios
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p. 913 - 916
(2007/10/03)
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- PHOTOLYSIS OF 2-AMINO- AND 2-METHYLAMINO-1,4-NAPHTHOQUINONE
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Pyrex-filtered sunlight irradiation of solutions of 2-amino-1,4-naphthoquinone unexpedtedly failed to produce cyclobutane dimers.Irradiation in acetic anhydride led to the formation of the trimeric 6--dibenzocarbazole-5,13:7,12-diquinone as well as 3,3'-diamino-2,2'-bi-carbazole-5,13:7,12-diquinone.Similar treatment of 2-methylamino-1,4-naphthoquinone afforded 6--dibenzocarbazole-5,13:7,12-diquinone and 6-methyl-dibenzocarbazole-5,13:7,12-diquinone
- Martins, F. J. C.,Viljoen, A. M.,Strydom, S. J.,Fourie, L.,Wessels, P. L.
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p. 591 - 598
(2007/10/02)
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