- Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2 H)-ones from Substituted 2′-Aminochalcones
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An alternative and efficient one-step approach to develop small libraries of polysubstituted 4-styrylquinolines/4-styrylquinolin-2-ones and 9-styryldihydroacridin-1-ones is described. According to this approach, new series of these compounds were straightforwardly synthesized in high yields starting from synthetically available 2′-aminochalcones and 1,3-dicarbonyl compounds in glacial acetic acid as a catalyst via the Friedl?nder reaction. Our approach also offers an expeditious way to access novel molecular hybrids in whose structures styryl and chalcone fragments are attached at the C4 and C3 positions, respectively, of the quinoline ring. All synthesized compounds were fully characterized by means of IR, HRMS and NMR techniques, and most were screened at the National Cancer Institute, USA, for their antitumor activity.
- Acosta, Lina M.,Ardila, Diana,Cobo, Justo,Guerrero, Sergio A.,Nogueras, Manuel,Palma, Alirio,Plata, Esteban,Meléndez, Angie,Rodríguez, Diego
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- A Novel Approach to N-Tf 2-Aryl-2,3-Dihydroquinolin- 4(1H)-ones via a Ligand-Free Pd(II)-Catalyzed Oxidative Aza-Michael Cyclization
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2-Aryl-2,3-dihydroquinolin-4(1H)-ones have recently been identified as important structures with potent biological activities such as antitumor and antidiabetic effect. Herein, a total of 25 novel N-Tf 2-aryl-2,3-dihydroquinolin-4(1H)-ones were expediently synthesized via the oxidative aza-Michael cyclization of N-Tf-2′-aminodihydrochalcones by ligand-free palladium(II) catalysis. This study presents a new synthetic approach to yield N-Tf 2-aryl-2,3-dihydroquinolin-4(1H)-ones, which can be easily transformed into pharmacologically interesting aza-flavanones and other N-heterocycles, such as quinolines and tetrahydroquinolines, in yields up to 84 %. This methodology has various advantages, which includes short reaction times under mild conditions and suitable functional group tolerance. Furthermore, a plausible mechanism was proposed and demonstrated by kinetic analysis.
- Kim, Young Min,Yoo, Hyung-Seok,Son, Seung Hwan,Kim, Ga Yeong,Jang, Hyu Jeong,Kim, Dong Hwan,Kim, Soo Dong,Park, Boyoung Y.,Kim, Nam-Jung
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p. 618 - 622
(2020/12/15)
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- Chelating Group Enabled Palladium-Catalyzed Regiodivergent Carbonylative Synthesis of 2,3-Dihydroquinolin-4(1H)-ones
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A new procedure on palladium-catalyzed carbonylative cyclization of N-(2-pyridyl)sulfonyl (N-SO2Py)-2-iodoanilines with terminal alkenes has been developed for the rapid construction of dihydroquinolin-4(1H)-one scaffolds. Enabled by the chelat
- Ying, Jun,Wang, Jian-Shu,Yao, Lingyun,Lu, Wangyang,Wu, Xiao-Feng
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p. 14565 - 14569
(2020/10/19)
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- Transformation of fluorinated 2-alkynylanilines by various catalytic systems
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Simple and efficient approaches to the synthesis of fluorinated benzoazaheterocycles with good yields are reported. Firstly a series of polyfluorinated 2-alkynylanilines – the versatile building blocks – was synthesized by the Sonogashira reaction of o-iodoaniline with terminal alkynes. Then the transformations of the obtained 2,3,4-trifluo-6-alkynilanilines in the presence of KOH or PdCl2 in MeCN, and in the presence of monohydrate of p-toluenesulfonic acid (p-TSA?H2O) in MeOH, EtOH or benzene were investigated. It was found that Ph- and n-Bu-containing alkynylanilines by action of PdCl2 in MeCN underwent an intramolecular cyclization reaction to produce the corresponding indoles in high yields. The reaction of KOH with alkynes containing the tertiary alcohol function at the triple bond produced the unsubstituted on the pyrrole ring indole. It was found that fluorinated 2-alkynilanilines can be transformated into indoles, 2-arylketones and 2,3-dihydroquinolines by action of p-TSA?H2O in boiling alcohols, depending on the substituent at the triple bond. The use of benzene as a solvent in the reaction of p-TSA?H2O with polyfluorinated alkynes, bearing an alcohol group resulted in representative series of 2,3-dihydroquinolinones containing a substituents R1 and R2 in the 2nd position of their structure (R = H, H; Me, Me; H, i-Pr; H, Ph).
- Politanskaya, Larisa,Petyuk, Maxim,Tretyakov, Evgeny
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- Organometallic titanocene complex as highly efficient bifunctional catalyst for intramolecular Mannich reaction
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Bifunctional catalysts bearing two catalytic sites, Lewis acidic organometallic titanocene and Br?nsted acidic COOH, have been assembled in situ from Cp2TiCl2 with carboxylic acid ligands, showing high catalytic activity over an intramolecular Mannich reaction towards synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. The determination of the bifunctional catalyst Cp2Ti(C8H4NO6)2 was elucidated by single X-ray HR-MS and investigation of catalytic behavior. In particular, masking the Br?nsted acidic COOH catalytic site with dormant COOMe lowered the reaction yield greatly, indicating that two catalytic sites work together to maintain high catalytic efficiency.
- Wang, Yunyun,Jian, Yajun,Wu, Ya,Sun, Huaming,Zhang, Guofang,Zhang, Weiqiang,Gao, Ziwei
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- Titanocene complex with oxygen-containing carboxylic acid as ligand as well as preparation method and application of titanocene complex
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The invention discloses a titanocene complex with oxygen-containing carboxylic acid as well as a preparation method and an application of the titanocene complex. The structural formula of the complexis shown in the description. The titanocene complex is p
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Paragraph 0039; 0040; 0042
(2018/11/03)
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- Zirconyl Nitrate as an Efficient Catalyst for Facile Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1 H)-one Derivatives in Aqueous Medium
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A simple, green, and efficient method is introduced for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1 H)-ones under mild reaction conditions with improved yields by intramolecular cyclization of o -aminochalcones with zirconyl nitrate [Zn(O)(NO 3/
- Gorepatil, Amarsinha,Gorepatil, Pratapsinha,Gaikwad, Mahadev,Mhamane, Dattakumar,Phadkule, Ajit,Ingle, Vilas
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p. 235 - 237
(2017/09/28)
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- 2-aryl-2,3-dihydro-4(1H)-quinolinone semicarbazone compound and application thereof
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The invention relates to the field of medicine technology, and a series of novel 2-aryl-2,3-dihydrogen-4(1H)-quinolinone semicarbazone derivatives (I) and pharmaceutically acceptable salts, solvates,optical isomers or polymorphs are designed and synthesized. The derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph can be mixed as an active ingredient witha pharmaceutically acceptable carrier to prepare a pharmaceutical composition. A double dilution method is used for test of the antifungal activity of the derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph, and the results show that the derivative has stronger killing effect on clinically common pathogenic fungi, and is expected to overcome the defects oflarge toxic and side effects, easy generation of drug resistance of azole antifungal medicines which are widely used clinically. The specific formula is shown in the description.
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- Synthesis, molecular modeling and biological evaluation of aza-flavanones as α-glucosidase inhibitors
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An efficient acid catalyzed methodology has been employed to synthesize a variety of aza-flavanones and their α-glucosidase inhibitory activity is evaluated using acarbose, miglitol and voglibose as reference standards. Molecular modeling studies were per
- Kasturi, Sivaprasad,Surarapu, Sujatha,Bathoju, Chandra Chary,Uppalanchi, Srinivas,Dwivedi, Shubham,Perumal, Yogeeswari,Sigalapalli, Dilep Kumar,Babu, Bathini Nagendra,Ethiraj, Krishna S.,Anireddy, Jaya Shree
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p. 1618 - 1630
(2017/08/22)
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- Method for synthesizing 2-aryl-2,3-dihydro-4(1H)-quinolinone derivative under catalysis of high-acidity ionic liquid
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The invention discloses a method for synthesizing a 2-aryl-2,3-dihydro-4(1H)-quinolinone derivative under the catalysis of high-acidity ionic liquid, belonging to the technical field of chemical material preparation. According to the method, o-aminoacetophenone and aromatic aldehyde are used as reaction raw materials and subjected to a reaction under the catalysis of a high-acidity ionic liquid catalyst so as to synthesize the 2-aryl-2,3-dihydro-4(1H)-quinolinone derivative. Through selection of specific high-acidity ionic liquid as the catalyst and optimization of reaction process parameters, the method provided by the invention can effectively overcome the disadvantages of great usage amounts of catalysts, poor recycling performance, complex product purification process and insufficient product yield in conventional synthesis processes.
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Paragraph 0041; 0042; 0043
(2017/10/07)
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- Use of Mesoporous Molecular Sieves in the Production of Fine Chemicals: Preparation of Dihydroquinolinones of Pharmaceutical Interest from 2′-Aminochalcones
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Solid catalysts can be an alternative to homogeneous mineral Br?nsted and Lewis acids for the synthesis of pharmaceuticals provided that the diffusional and adsorption properties of the reactants and products can be controlled. Structured micro and especi
- Climent, María J.,Corma, Avelino,Iborra, Sara,Martí, Laura
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p. 1335 - 1345
(2016/04/20)
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- A Green, Solvent-Free, Microwave-Assisted, High-Yielding YbCl3Catalyzed Deprotection of THP/MOM/Ac/Ts Ethers of Chalcone Epoxide and 2′-Aminochalcone and Their Sequel Cyclization
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Under microwave and solvent-free conditions, YbCl3efficiently catalyzed the deprotection of tetrahydropyran-2-yl, methoxymethyl (MOM), acetyl, and tosyl groups and sequel cyclization of chalcone epoxide to 2-hydroxyindanone and 2′-aminochalcone to aza-flavanone. The reaction afforded the products in excellent yield (78–99%) at 850 W microwave heating within 1–5 min under eco-friendly conditions. The merits of the presented protocol include high yield, use of microwave irradiation, solvent-free condition, catalyst reusability, and no need for purification with column chromatography. The present method is very much milder but more advanced than those reported earlier.
- Kumar, Sumit,Verma, Nishant,Parveen, Iram,Ahmed, Naseem
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supporting information
p. 2111 - 2122
(2016/11/23)
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- C–C bond-forming reactions of ground-state aryl halides under reductive activation
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Under basic conditions aryl halides can undergo SRN1 reactions, BHAS reactions and benzyne formations. Appropriate complex substrates afford an opportunity to study inherent selectivities. SRN1 reactions are usually favoured under ph
- Emery, Katie J.,Tuttle, Tell,Kennedy, Alan R.,Murphy, John A.
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p. 7875 - 7887
(2016/11/17)
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- [C8dabco]Br: a mild and convenient catalyst for intramolecular cyclization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones
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[Figure not available: see fulltext.] A new and convenient synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been described using the intramolecular cyclization of 2-aminochalcones catalyzed by 1-octyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide ([Cs
- Derabli, Chamseddine,Mahdjoub, Sara,Boulcina, Raouf,Boumoud, Boudjemaa,Merazig, Hocine,Debache, Abdelmadjid
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- A general and efficient synthesis of 5,6-dihydrodibenzo[b,h][1,6]naphthyridine derivatives
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A two-step procedure for the synthesis of dihydrodibenzonaphthyridine derivatives from benzaldehydes and 2-aminoacetophenones, proceeding through a substituted dihydroquinolone intermediate, is described. The synthetic protocol allows for a versatile and robust coupling method between a range of 2-aminoacetophenones or 2-aminobenzophenones and a selection of substituted dihydroquinolones.
- Dobrowolski, Jeremy C.,Katen, Alice,Fraser, Benjamin H.,Bhadbhade, Mohan,Black, David StC.,Kumar, Naresh
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p. 5442 - 5445
(2016/11/19)
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- β-Cyclodextrin in water: Highly facile biomimetic one pot deprotection of phenolic THP/MOM/Ac/Ts ethers and concomitant regioselective cyclization of chalcone epoxides and 2′-aminochalcones
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A mild and efficient one-pot deprotection of THP/MOM/Ac/Ts ethers and the concomitant cyclization of chalcone epoxides to 2-hydroxyindanones or 2′-aminochalcones to aza-flavanones using β-cyclodextrin in water has been developed. β-CD was found to be highly effective at carrying out the deprotection and sequential transformations in an eco-friendly environment affording moderate to excellent yields (59-99%) at 60 °C in 8-22 min. Water, an eco-friendly reaction medium, has been utilized for the first time in this reaction. The merits of the presented protocol include the high yields and catalyst reusability and the protocol precludes the use of metals and organic solvents. The present method is much milder but more advanced than those reported earlier.
- Kumar, Sumit,Verma, Nishant,Ahmed, Naseem
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p. 85128 - 85138
(2015/10/28)
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- Mild and Efficient Silver(I) Triflate Catalyzed Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1 H)-ones, and Their Antioxidant Activities
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Biologically interesting 2-aryl-2,3-dihydroquinolin-4(1H)-ones were synthesized using a mild and efficient one-pot procedure starting from o-aminoacetophenones and aromatic aldehydes in the presence of silver(I) triflate. This synthetic protocol provides rapid access to a variety of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. This technique has several advantages, such as the use of easily available starting materials, the efficiency of the catalyst, a simple operation, and tolerance of a wide range of functionality in the aldehydes. Screening of the synthesized compounds for their antioxidant properties revealed that two compounds (with EC50 = 15.42 μM and 15.16 μM) exhibit a potent free-radical scavenging ability towards TEAC free radicals compared to the standard, Trolox.
- Pandit, Rameshwar Prasad,Sharma, Kavita,Lee, Yong Rok
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p. 3881 - 3890
(2015/12/18)
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- Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2-Substituted 2,3-Dihydro-4-quinolones by a Protecting-Group-Free Approach
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Chiral 2-substituted 2,3-dihydro-4-quinolones were synthesized based on the chiral phosphoric acid catalyzed intramolecular aza-Michael addition reaction using N-unprotected 2-aminophenyl vinyl ketones as substrates in good yields with high enantioselectivities. (Chemical Equation Presented).
- Saito, Kodai,Moriya, Yuka,Akiyama, Takahiko
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supporting information
p. 3202 - 3205
(2015/07/15)
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- 2-aminobenzaldehydes as versatile substrates for rhodium-catalyzed alkyne hydroacylation: Application to dihydroquinolone synthesis
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Amine for it! A cationic rhodium catalyst, which was assembled insitu from commercial components, promoted the reaction of a range of simple 2-aminobenzaldehydes with terminal and internal alkynes in a series of intermolecular hydroacylation reactions. The products of this reaction, amino-substituted enones, were efficiently converted into the corresponding dihydro-4-quinolones.
- Castaing, Matthias,Wason, Sacha L.,Estepa, Beatriz,Hooper, Joel F.,Willis, Michael C.
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supporting information
p. 13280 - 13283
(2014/01/06)
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- Design and synthesis of aza-flavones as a new class of xanthine oxidase inhibitors
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In an attempt to develop non-purine-based xanthine oxidase (XO) inhibitors, keeping in view the complications reported with the use of purine-based XO inhibitors, the flavone framework (a class possessing XO inhibitory potential) was used as lead structure for further optimization. By means of structure-based classical bioisosterism, quinolone was used as an isoster for chromone (a bicyclic unit present in flavones), owing to the bioactive potential and drug-like properties of quinolones. This type of replacement does not alter the shape and structural features required for XO inhibition, and also provides some additional interaction sites, without the loss of hydrogen bonding and hydrophobic and arene-arene interactions. In the present study, a series of 2-aryl/heteroaryl-4-quinolones (aza analogs of flavones) was rationally designed, synthesized and evaluated for in vitro XO inhibitory activity. Some notions about structure-activity relationships are presented indicating the influence of the nature of the 2-aryl ring on the inhibitory activity. Important interactions of the most active compound 3l (IC50 = 6.24 μM) with the amino acid residues of the active site of XO were figured out by molecular modeling. To develop non-purine-based xanthine oxidase inhibitors, the flavone framework was used as lead structure for further optimization. By means of structure-based classical bioisosterism, quinolone was used as an isoster for chromone. This type of replacement does not alter the shape and structural features required for xanthine oxidase inhibition. The rationally designed and synthesized series of 2-aryl/heteroaryl-4-quinolones (aza analogs of flavones) was evaluated for in vitro xanthine oxidase inhibitory activity. Copyright
- Dhiman, Rajni,Sharma, Sahil,Singh, Gagandip,Nepali, Kunal,Singh Bedi, Preet Mohinder
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- Aza analogs of flavones as potential antimicrobial agents
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In search for the new antimicrobial agents owing to drug resistant bacteria and fungi, a series of rationally designed aza analogs of flavones has been designed and synthesized. The design of the analogs involved incorporation of quinolone nucleus within
- Sharma, Sahil,Thakur, Vikas,Ojha, Ritu,Budhiraja, Abhishek,Nepali, Kunal,Singh Bedi, Preet Mohinder
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p. 327 - 334
(2013/07/26)
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- Highly efficient and green synthesis of flavanones and tetrahydroquinolones
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Highly efficient and green catalytic conversion of 2′-hydroxy and 2′-amino chalcones to flavanones and tetrahydroquinolones is reported herein. 2′-Hydroxy and 2′-amino chalcones can be almost completely converted to flavanones and tetrahydroquinolones in just 2 min in the presence of piperidine and KOH under room temperature. Liquiritigenin is also efficiently synthesized under similar conditions.
- Zheng, Xuxu,Jiang, Heyan,Xie, Jingjing,Yin, Zhongyi,Zhang, Haidong
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p. 1023 - 1029
(2013/03/13)
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- Synthesis of flavanones, azaflavanones, and thioflavanones catalyzed by PMA-SiO2 as a mild, efficient, and reusable catalyst
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Cyclization of a variety of chalcones to flavanones catalyzed by 1 mol% phosphomolybdic acid (PMA) supported on silica as a mild, efficient, and reusable catalyst was carried out in high yields. PMA-SiO2 is an efficient, inexpensive, and green catalyst which gave high conversion yields and could be recycled up to three times without significant loss in activity. Springer-Verlag 2011.
- Sakirolla, Raghavendra,Yaeghoobi, Marzieh,Rahman, Noorsaadah Abd.
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experimental part
p. 797 - 800
(2012/09/07)
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- Aza-Flavanones as potent cross-species microRNA inhibitors that arrest cell cycle
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aza-Flavanones have been identified as a new class of selective microRNA inhibitors. These compounds were found to arrest cell cycle via a novel cross species microRNA-dependent regulatory pathway interpreting an unexpected link between cell cycle arrest and microRNA mediated control in cancer.
- Chandrasekhar, Srivari,Pushpavalli, Sreerangam N.C.V.L.,Chatla, Srinivas,Mukhopadhyay, Debasmita,Ganganna, Bogonda,Vijeender, Kandi,Srihari, Pabbaraja,Reddy, Chada Raji,Janaki Ramaiah,Bhadra, Utpal
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supporting information; experimental part
p. 645 - 648
(2012/03/26)
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- An efficient and rapid intramolecular aza-Michael addition of 2′-aminochalcones using ionic liquids as recyclable reaction media
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A new, convenient, and efficient method for the intramolecular aza-Michael addition reaction of 2′-aminochalcones is developed using 1-n-butyl-3-methylimidazolium tetrafluoroborate as the solvent and catalyst. The ionic liquid is successfully regenerated and reused.
- Chelghoum,Bahnous,Bouraiou,Bouacida,Belfaitah
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p. 4059 - 4061
(2012/08/28)
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- (±)-2-Aryl-2,3-dihydro-4(1H)-quinolinones by a tandem reduction-Michael addition reaction
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An efficient synthesis of (±)-2-aryl-2,3-dihydro-4(1H)-quinolinones has been developed from chalcones prepared from 2′-nitroacetophenone and a series of substituted benzaldehydes. The cyclization sequence is initiated by reduction of the nitro group under dissolving metal conditions using iron powder in concentrated hydrochloric acid. Milder conditions, using acetic acid or acetic acid-phosphoric acid as the reaction medium, were less satisfactory. Procedural details as well as a mechanistic discussion and reaction optimization studies are presented.
- Bunce, Richard A.,Nammalwar, Baskar
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experimental part
p. 613 - 619
(2011/07/31)
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- ZnCl2-catalyzed intramolecular cyclization reaction of 2-aminochalcones using polymer-supported selenium reagent: Synthesis of 2-phenyl-4-quinolones and 2-phenyl-2,3-dihydroquinolin-4(1 H)-one
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A new and efficient method for the synthesis of 2-phenyl-4-quinolones and 2-phenyl-2,3-dihydroquinolin-4(1H)-ones is described. The reaction involves ZnCl2-mediated polystyrene-supported selenium-induced intramolecular cyclization of 2-amino-chalcones and subsequent traceless or functionalizing cleavage of selenium linker. Georg Thieme Verlag Stuttgart - New York.
- Tang,Chen, Bangzheng,Zhang, Lianpeng,Li, Wen,Lin, Jun
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experimental part
p. 707 - 711
(2011/04/26)
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- Lithium tetrafluoroborate catalyzed highly efficient inter- and intramolecular aza-Michael addition with aromatic amines
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Lithium tetrafluoroborate has been demonstrated for the first time to be an efficient catalyst in intermolecular aza-Michael addition aromatic amines to electron deficient alkenes. Suitability of the same catalyst in intramolecular aza-Michael addition leading 2-aryl-2,3-dihydroquinolin-4(1H) ones has also been described.
- Lad,Kulkarni,Desai,Wadgaonkar
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experimental part
p. 1059 - 1064
(2012/03/11)
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- Ytterbium(III) triflate: An efficient and simple catalyst for isomerization of 2′-hydroxychalcone and 2′-aminochalcones in ionic liquid
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Isomerization of 2′-hydroxychalcone and 2′-aminochalcone have been investigated using ytterbium(III) trifluromethanesulfonate {Yb(OTf) 3} (30 mol %) as Lewis acid catalyst in [bmim][BF4] ionic liquid. The effect of different metal triflates as Lewis acid, catalyst loading and reaction media was studied for this isomerization reaction. Advantages of the methodology include short reaction time, excellent yields, catalytic use of Lewis acid, and recovery and reuse of the catalyst. Copyright
- Rao, V. Kameswara,Rao, M. Sudershan,Kumar, Anil
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experimental part
p. 1356 - 1360
(2012/01/04)
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- Synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones using wet cyanuric chloride under solvent-free conditions
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A simple and facile synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been accomplished by isomerization of substituted 2'- aminochalcones under solvent-free conditions in the presence of wetcyanuric chloride as a catalyst.
- Yang, Chunguang,Fang, Lizhen,Wu, Liqiang,Yan, Fulin
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experimental part
p. 6031 - 6034
(2010/11/19)
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- Simple and efficient synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones using silica chloride as a new catalyst under solvent-free conditions
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A mild, efficient, and high-yielding method for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones from their corresponding 2-amino chalcones using silica chloride (SiO2Cl) under solvent-free conditions is described. A series of 2-aryl-2,3-dihydroquinolin-4(1H)-ones containing both electron-donating and electron-withdrawing substituents were synthesized.
- Muthukrishnan,Mujahid,Punitharasu,Dnyaneshwar
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scheme or table
p. 1391 - 1398
(2010/06/21)
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- Antimony trichloride: An efficient and mild catalyst for cyclization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones
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Antimony trichloride is an efficient catalyst for the cyclization of 2-amino chalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under mild reaction conditions and in almost quantitative yields. Copyright Taylor & Francis Group, LLC.
- Bhattacharya,Kundu, Pradip,Maiti, Gourhari
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experimental part
p. 476 - 481
(2010/04/04)
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- The cyclisation of 2'-aminochalcones using silica-supported Yb(OTf)3 under solvent-free conditions
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Silica-supported Yb(OTf)3 is utilised as a catalyst for the synthesis of 2-substituted dihydroquinolinones from 2'-amino chalcones in good yields. The catalyst is easily prepared and is active under solvent-free conditions and environmentally friendly con
- Li, Jianjun,Jin, Linyong,Yu, Chuanming,Su, Weike
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experimental part
p. 170 - 173
(2009/11/30)
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- Ionic liquid catalyzed expeditious synthesis of 2-aryl-2,3-dihydroquinolin- 4(1H)-ones and 2-aryl-2,3-dihydro-4H-chromen-4-ones under microwave irradiation
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(Chemical Equation Presented) A facile and convenient synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-one and 2-aryl-2,3-dihydro-4Hchromen-4-one has been described using ionic liquid catalyzed intramolecular cyclization of the corresponding 2′-aminochalcones and 2′-hydroxychalcones, respectively. The rapid and fairly general protocol affords product in good yield. Ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, was recovered and reused without loosing its efficiency.
- Kumar, Dalip,Patel, Gautam,Kumar, Anil,Roy, Ram K.
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experimental part
p. 791 - 795
(2009/12/01)
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- Eco-friendly polyethylene glycol promoted Michael addition reactions of α,β-unsaturated carbonyl compounds
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Intra- and inter-nucleophilic addition reactions of different α,β-unsaturated carbonyl compounds were found to be highly effective without any additives in PEG-400 as a recyclable reaction medium under neutral conditions.
- Kumar, Dalip,Patel, Gautam,Mishra, Braja G.,Varma, Rajender S.
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scheme or table
p. 6974 - 6976
(2009/04/07)
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- Alumina supported-CeCl3·7H2O-NaI: an efficient catalyst for the cyclization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent free conditions
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We recently advanced silica gel supported-TaBr5 as an efficient catalyst for the isomerization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent free conditions (Tetrahedron Lett. 2006, 47, 2725-2729)
- Ahmed, Naseem,van Lier, Johan E.
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- A simple and facile solventless procedure for the cyclization of 2′-amino- and 2′-hydroxy-chalcones using silica-supported sodium hydrogen sulphate as heterogenous catalyst
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A simple environmentally friendly method for the cyclization of 2′-amino- and 2′-hydroxy-chalcones under solventless conditions using silica-supported sodium hydrogen sulphate has been reported.
- Hemanth Kumar,Perumal
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p. 1079 - 1083
(2007/10/03)
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- Silica gel supported TaBr5: New catalyst for the facile and rapid cyclization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions
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Silica gel supported TaBr5 (5-10 mol %) is a new solid-support catalyst that can be used under solvent-free conditions for the facile and efficient isomerization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones. The catalyst is easily prepared, stable and employed under environmentally friendly conditions.
- Ahmed, Naseem,Van Lier, Johan E.
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p. 2725 - 2729
(2007/10/03)
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- Synthesis and characterization of [1]benzopyrano[4,3-d][1,3]benzooxazocin- 13-one and its derivatives
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This work describes the efficient synthesis of functionalized cleft molecules 6, 6a, 16, 16a, 17, 19 and 20 derived from benzopyrano[4,3-d][1,3] benzooxazocin-13-one. X-ray crystal structure analysis of compounds 6a and 16a revealed that the cleft angles of the planes of the benzopyran moiety and the p-methoxybenzene ring are 109.4° and 108.6°, respectively. The conformation of the aromatic ring at the bridgehead of 16, 16a and 20 is restricted by the gem-dimethyl groups on the C-9 position and the methyl group on the nitrogen atom in the ring. Georg Thieme Verlag Stuttgart.
- Wang, Jen-Fei,Liao, Yuan-Xiu,Kuo, Pei-Yu,Gau, Yung-Her,Yang, Ding-Yah
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p. 2791 - 2794
(2008/02/11)
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- Indium(III) Chloride/Silica Gel-Promoted Facile and Rapid Cyclization of 2-Aminochalcones to 2-Aryl-2,3-dihydroquinolin-4(1H)-ones under Solvent-Free Conditions
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A convenient environmentally friendly method for the cyclization of 2-aminochalcones to 2-aryl-2,3-dihydroquinolin-4(1H)-ones on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent has been repor
- Kumar, K. Hemanth,Muralidharan,Perumal
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- Bifunctional Nanocrystalline MgO for Chiral Epoxy Ketones via Claisen-Schmidt Condensation-Asymmetric Epoxidation Reactions
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Design and development of a truly nanobifunctional heterogeneous catalyst for the Claisen?Schmidt condensation (CSC) of benzaldehydes with acetophenones to yield chalcones quantitatively followed by asymmetric epoxidation (AE) to afford chiral epoxy ketones with moderate to good yields and impressive ee's is described. The nanomagnesium oxide (aerogel prepared) NAP-MgO was found to be superior over the NA-MgO and CM-MgO in terms of activity and enantioselectivity as applicable in these reactions. An elegant strategy for heterogenization of homogeneous catalysts is presented here to evolve single-site chiral catalysts for AE by a successful transfer of molecular chemistry to surface metal?organic chemistry with the retention of activity, selectivity/enantioselectivity. Bronsted hydroxyls are established as sole contributors for the epoxidation reaction, while they add on to the CSC, which is largely driven by Lewis basic O2-sites. Strong hydrogen-bond interactions between the surface ?OH on MgO and ?OH groups of diethyl tartrate are found inducing enantioselectivity in the AE reaction. Thus, the nanocrystalline NAP-MgO with its defined shape, size, and accessible OH groups allows the chemisorption of TBHP, DET, and olefin on its surface to accomplish single-site chiral catalysts to provide optimum ee's in AE reactions. Copyright
- Choudary, Boyapati M.,Kantam, Mannepalli L.,Ranganath, Kalluri V. S.,Mahendar, Koosam,Sreedhar, Bojja
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p. 3396 - 3397
(2007/10/03)
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- Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2',3',4'-substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents
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A novel series of 6,7,2',3',4'-substituted-1,2,3,4-tetrahydro-2-phenyl- 4-quinolones were synthesized and evaluated for interactions with tubulin and for cytotoxic activity against a panel of human tumor cell lines, including ileocecal carcinoma (HCT-8), breast cancer (MCF-7), lung carcinoma (A-549), epidermoid carcinoma of the nasopharynx (KB), renal cancer (CAKI-1), and melanoma cancer (SKMEL-2). Most compounds (18, 20, 22-27) showed potent cytotoxic and antitubulin effects. The most active compounds (23, 26, 27) demonstrated strong cytotoxic effects with ED50 values in the nanomolar or subnanomolar range in almost all tumor cell lines. Three active racemates (20, 22, 25) were separated into the enantiomers, and generally, the optically pure (-)-isomers (20a, 22a, 25a) exhibited greater biological activity than the racemates or (+)-isomers. Cytotoxicity and antitubulin activity were closely correlated, with the most active compounds (23, 26, 27) having effects comparable to those of colchicine, podophyllotoxin, and combretastatin A-4.
- Xia, Yi,Yang, Zheng-Yu,Xia, Peng,Bastow, Kenneth F.,Tachibana, Yoko,Kuo, Sheng-Chu,Hamel, Ernest,Hackl, Torben,Lee, Kuo-Hsiung
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p. 1155 - 1162
(2007/10/03)
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- Microwave-Assisted Isomerization of 2′-Aminochalcones on Clay: An Easy Route to 2-Aryl-1,2,3,4-tetrahydro-4-quinolones
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A simple and environmentally benign method for the conversion of 2′-aminochalcones to 2-aryl-1,2,3,4-tetrahydro-4-quinolones is described which occurs under mild and solvent-free conditions on montmorillonite K 10 clay surface; microwave irradiation facil
- Varma, Rajender S.,Saini, Rajesh K.
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p. 857 - 858
(2007/10/03)
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- Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones
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o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.
- Mahanty, Jyan S.,De, Mahuya,Das, Palas,Kundu, Nitya G.
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p. 13397 - 13418
(2007/10/03)
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- A New Two-Step Synthesis of Quinolone Alkaloids Based on the Regioselective Addition of Organometallic Reagents to 4-Silyloxyquinolinium Triflates
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Organolithium- as well as Grignard reagents regioselectively add to N-protected 4-silyloxyquinolinium triflates with yields ranging from 38 to 93 %; the Cbz-protected C-2 adducts are easily transformed in a single operation to give the corresponding 2-substituted 4-quinolones in nearly quantitative yields.
- Beifuss, Uwe,Ledderhose, Sabine
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p. 313 - 315
(2007/10/03)
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- Intramolecular Amination of Olefins. Synthesis of 2-Substituted-4-quinolones from 2-Nitrochalcones catalysed by Ruthenium
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2-Substituted-4-quinolones 2 and the correspnding 2,3-dihydro-2-substituted-4-quinolones 3 have been obtained by reduction with CO at 170 deg C and 30 atm of 2-nitrochalcones 1, catalysed by Ru3(CO)12 with DIAN-Me as co-catalyst in ethanol-water.
- Tollari, Stefano,Cenini, Sergio,Ragaini, Fabio,Cassar, Lucia
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p. 1741 - 1742
(2007/10/02)
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- Fragmentation pathways in the electron impact mass spectra of 2-aryl-1,2,3,4-tetrahydro-4-quinolones
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The major feagmentation pathways in the electron impact mass spectra of a series of 2-aryl-1,2,3,4-tetrahydro-4-quinolones have been determined using a combination of low- and high-resolution mass spectrometry and matastable peak analysis.
- Kaye, Perry T.,Mphahlele, M. Jack
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- Synthesis of Quinolines and 2,3-Dihydro-4(1H)-quinolones. Palladium Catalysed Reaction of o-Iodoanilides with Acetylenic Carbinols
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A facile and general synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones was accomplished through palladium catalysed reaction of o-iodoanilides with acetylenic carbinols.Key Words: quinolines; 2,3-dihydro-4(1H)-quinolones; palladium catalysis; o-iodoanilines; acetylenic carbinols.
- Kundu, Nitya G.,Mahanty, Jyan S.,Das, Palas,Das, Biswajit
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p. 1625 - 1628
(2007/10/02)
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- Schmidt reaction on 2-aryl-1,2,3,4-tetrahydro-4-quinolone
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Synthesis and stereochemistry of 2-aryl-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one and 2-aryl-2,3-dihydro-4H-tetrazolo[1,5-d]-1H-1,4-benzodiazepine is reported by the Schmidt reaction on 2-aryl-1,2,3,4-tetrahydro-4-quinolone.
- Tokes,Litkei
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p. 895 - 902
(2007/10/02)
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