- Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization
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Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.
- Son, Seung Hwan,Cho, Yang Yil,Yoo, Hyung-Seok,Lee, Soo Jin,Kim, Young Min,Jang, Hyu Jeong,Kim, Dong Hwan,Shin, Jeong-Won,Kim, Nam-Jung
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p. 14000 - 14006
(2021/04/22)
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- Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide
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An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.
- Bismuto, Alessandro,Boehm, Philip,Morandi, Bill,Roediger, Sven
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supporting information
p. 17887 - 17896
(2020/08/19)
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- Temperature-Controlled Stereodivergent Synthesis of 2,2′-Biflavanones Promoted by Samarium Diiodide
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In this work, the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2′-biflavanones promoted by samarium diiodide is reported. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2′-biflavanones bearing different substitution patterns at the aromatic ring in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2′-biflavanones and the selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single-crystal X-ray diffraction experiments.
- Soto, Martín,Soengas, Raquel G.,Silva, Artur M. S.,Gotor-Fernández, Vicente,Rodríguez-Solla, Humberto
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supporting information
p. 13104 - 13108
(2019/10/21)
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- Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides
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Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.
- Cheng, Kang,Chen, Jinkang,Jin, Licheng,Zhou, Jian,Jiang, Xinpeng,Yu, Chuanming
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p. 392 - 398
(2019/09/03)
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- Regioselective hydrodehalogenation of aromatic α-and β-halo carbonyl compounds by cui in isopropanol
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An operationally efficient and regioselective hydrodehalogenation methodology of aromatic α-and β-halo carbonyl compounds has been developed using CuI in isopropanol at 90 °C under basic condition. The catalytic system effectively dehalogenates chloride, bromide, and iodide groups and af-forded high yield (up to 97 %) as carbonyl compounds. The methodology is environmentally friendly and demonstrates excellent tolerance to a broad range of electronically rich and poor substituents.
- Parveen, Iram,Khan, Danish,Ahmed, Naseem
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p. 759 - 764
(2019/01/09)
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- Iodine-mediated direct synthesis of 3-iodoflavones
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Molecular iodine has been used for the regioselective, one pot, direct synthesis of 3-iodoflavones from 2′-allyloxy chalcones, 2′-hydroxy chalcones and flavones. Allyl deprotection, cyclization dehydrogenation and α-iodination of 2′-allyloxychalcones has been achieved in a single step to offer 3-iodoflavones.
- Patil, Avinash M.,Kamble, Dayanand A.,Lokhande, Pradeep D.
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p. 1299 - 1307
(2018/04/05)
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- Novel and Efficient Access to Flavones under Mild Conditions: Aqueous HI-Mediated Cascade Cyclization/Oxidative Radical Reaction of 2-Propynolphenols
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Herein we disclose a metal-free and efficient method for the direct conversion of 2-propynolphenols to biologically important flavones using aqueous HI as the promoter. This transformation was proved via 4-iodo-2H-chromenes intermediate, which was simultaneously conversed to corresponding flavones by a Csp2?I bond cleavage and a C–O bond formation under air.
- Song, Xian-Rong,Li, Ren,Yang, Tao,Chen, Xi,Ding, Haixin,Xiao, Qiang,Liang, Yong-Min
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supporting information
p. 5548 - 5552
(2018/10/24)
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- Carbonylative Sonogashira annulation sequence: One-pot synthesis of 4-quinolone and 4H-chromen-4-one derivatives
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Carbonylative Sonogashira annulation sequence for one pot synthesis of 4-quinolone and 4H-chromen-4-one has been developed in presence of Pd-NHC catalyst. Substituted 2-iodoaniline and 2-iodophenol independently underwent in the carbonylative Sonogashira
- Ghosh, Prasanjit,Nandi, Aritra Kumar,Das, Sajal
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p. 2025 - 2029
(2018/04/25)
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- A transition-metal-free fast track to flavones and 3-arylcoumarins
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A highly regioselective and transition-metal free one-pot arylation of chromenones with arylboronic acids has been achieved employing K2S2O8. The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.
- Golshani, Mostafa,Khoobi, Mehdi,Jalalimanesh, Nafiseh,Jafarpour, Farnaz,Ariafard, Alireza
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supporting information
p. 10676 - 10679
(2017/10/06)
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- Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes
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The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.
- Yue, Yixia,Peng, Jinsong,Wang, Deqiang,Bian, Yunyun,Sun, Peng,Chen, Chunxia
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p. 5481 - 5486
(2017/05/24)
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- Guanidino-graphene catalysed synthesis of flavones via Aldol-Michael-oxidation
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Guanidino-graphene has been synthesized by the reaction of bromoamine with reduced graphene oxide and characterized by FT-IR, Raman, TGA, powder XRD, TEM, SEM, and zeta potential. It is a cheap, heterogeneous and environmentally benign solid base catalyst used for cascade Aldol-Michael-oxidation in the synthesis of chalcone, flavonoids.
- Mishra, Sweta,Arora, Smriti,Nagpal, Ritika,Chauhan, Shive Murat Singh
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p. 2525 - 2530
(2017/03/09)
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- Method for synthesizing flavonoids compound in one step by virtue of catalysis of 1,3-dialkylimidazolium oxometallate
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The invention discloses a method for synthesizing a flavonoids compound in one step by virtue of catalysis of 1,3-dialkylimidazolium oxometallate. The method is characterized by comprising the following steps: sequentially adding raw material benzaldehyde or benzaldehyde derivatives, raw material 2-hydroxyacetophenone or 2-hydroxyacetophenone derivatives, an ion liquid catalyst and an organic solvent into a reactor, stirring, heating to 50 to 90 DEG C, reacting for 2 to 7 hours at a constant temperature by taking oxygen or air as an oxidant, cooling, distilling under reduced pressure, carrying out the column chromatography, and re-crystallizing and separating to obtain the target product flavonoids compound. The method has the characteristics that the ion liquid is used as the catalyst, the yield of the flavonoids compound synthesized in one step reaches 85 percent or more, therefore, compared with the traditional synthetic method, the reaction flow is shortened, and the synthetic efficiency of the flavonoids compound is remarkably improved. The method has advantages of high product yield, low production cost, simple operation procedures, moderate reaction conditions and the like and is proved to be a novel method for high-efficiently synthesizing the flavonoids compound.
- -
-
Paragraph 0054; 0055; 0056
(2016/10/08)
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- Synthesis and antiviral activity of 2-aryl-4H-chromen-4-one derivatives against Chikungunya virus
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A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006-OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 μM, 0.45 μM and 2.02 μM, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of ≥100. Molecular docking simulation has been carried out to understand the possible mechanism of action.
- Badavath, Vishnu N.,Jadav, Surender S.,Pastorino, Boris,De Lamballerie, Xavier,Sinha, Barij N.,Jayaprakash, Venkatesan
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p. 1019 - 1024
(2016/11/25)
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- An efficient oxidative conversion of 2-aryl-2H-chromenes to the corresponding flavones by tert-butylhydroperoxide and copper bromide
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A simple and efficient method has been developed for the facile oxidation of chromenes to the corresponding flavones by tert-butylhydroperoxide (TBHP) in the presence of copper(II) bromide catalyst in toluene at 80 °C in a very short time. The reaction demonstrates excellent reactivity, functional group tolerance, and good to excellent yields without using conventional strong oxidizing agents.
- Banerjee, Dipanwita,Kayal, Utpal,Maiti, Gourhari
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p. 1667 - 1671
(2016/04/04)
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- Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones
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A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 lM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.
- Nayak, Badavath Vishnu,Ciftci-Yabanoglu,Bhakat, Soumendranath,Timiri, Ajay Kumar,Sinha, Barij N.,Ucar,Soliman, Mahmoud E. S.,Jayaprakash, Venkatesan
-
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- A versatile approach to flavones via a one-pot Pd(II)-catalyzed dehydrogenation/oxidative boron-Heck coupling sequence of chromanones
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A variety of flavones were expediently synthesized from readily accessible chromanones via a one-pot sequence involving Pd(ii)-catalyzed dehydrogenation and oxidative boron-Heck coupling with arylboronic acid pinacol esters. In particular, the use of arylboronic acid pinacol esters was found to significantly improve the yield of the reaction.
- Lee, Jun,Yu, Jihyun,Son, Seung Hwan,Heo, Jinyuk,Kim, Taelim,An, Ji-Young,Inn, Kyung-Soo,Kim, Nam-Jung
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p. 777 - 784
(2016/01/12)
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- Pyrrolidine and iodine catalyzed domino aldol-Michael-dehydrogenative synthesis of flavones
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A one pot synthesis of flavones is established from 2′- hydroxyacetophenones and substituted aromatic aldehydes. The method uses domino aldol-Michael-oxidation reaction catalyzed by pyrrolidine as a base and iodine as an oxidant in dimethyl sulfoxide.
- Naik, Mayuri M.,Tilve, Santosh G.,Kamat, Vijayendra P.
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p. 3340 - 3343
(2014/06/09)
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- Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones
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A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 μM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.
- Badavath, Vishnu Nayak,Ciftci-Yabanoglu,Bhakat, Soumendranath,Timiri, Ajay Kumar,Sinha, Barij N.,Ucar,Soliman, Mahmoud E.S.,Jayaprakash, Venkatesan
-
-
- Iodine catalyzed cascade synthesis of flavone derivatives from 2'-allyloxy-α,β-dibromochalcones
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Synthesis of flavones from 2'-allyloxy-α, β-dibromochalcones has been described. The iodine induced oxidative cyclization of 2'-allyloxy-α, β-dibromochalcones results into the formation of 3-bromoflavanones which ultimately gives flavones. Dehydrobromination of 3-bromoflavanone to give flavone is the preferred reaction over dehydrogenation.
- Nawghare, Beena R.,Gaikwad, Sunil V.,Raheem, Abdul,Lokhande, Pradeep D.
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p. 2284 - 2286
(2014/07/22)
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- Cyclization of 2'-hydroxychalcones to flavones using ammonium iodide as an iodine source - An eco-friendly approach
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Ammonium iodide on exposure to air decomposes to ammonia and iodine. The in situ generated iodine was used for the cyclization of 2'-hydroxychalcones to the corresponding flavones under solvent-free conditions in good to excellent yields. This method could serve as an attractive alternative to the existing methods for synthesis of flavones and the use of toxic molecular iodine is avoided. Copyright
- Kulkarni, Pramod S.,Kondhare, Dasharath D.,Varala, Ravi,Zubaidha, Pudukulathan K.
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p. 909 - 916
(2013/08/23)
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- Facile synthesis of new substituted aryl and heteroarylflavones by thermal and microwave assisted Suzuki-Miyaura coupling reaction
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Microwave assisted Suzuki-Miyaura coupling of 4′-bromoflavone 5 with substituted aryl and heteroarylboronic acids 6a-m gives high yields of aryl and heteroarylflavones 7a-m. Couplings have been carried out by three methods i) conventional heating with Pd(OCOCH3)2 catalyst, in solvent DMF(N,N-dimethylformamide) and base, aqueous Na2CO3 (2N) for 6-12 hr, at 110°C, yield 30-70%, ii) conventional heating with Pd[(C6H5)3P]4 catalyst, in DMF and base, aq. Na2CO3 (2N) for 6-12 hr, at 110°C, yield 40-72% and iii) Microwave heating with Pd[(C6H5)3P] 4 catalyst, in solvent (DMF+H2O, 5:2) and base, aq. Na2CO3 (2N) for 2-9 min, yield 50-87%. The substrate 4′-bromoflavone 5 has been synthesized from o-hydroxyacetophenone 1 in 3 steps. Esterification of 1 with 4-bromobenzoyl chloride 2 with montmorillonite-KSF catalyst, DCE (1,2-dichloroethane) and Et3N (triethylamine) which gives 2-(4- bromobenzoyloxy)acetophenone 3. Baker-Venkataraman rearrangement of 3 with pyridine and KOH further gives 1-(4-bromophenyl)-3-(2- hydroxyphenyl)propane-1,3-dione 4, followed by cyclization of 4 with methanolic sulfuric acid (2.5%) which yields 4'-bromoflavone 5, yield 82%.
- Joshi, Vidya,Govind Hatim, Jaywant
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experimental part
p. 1002 - 1010
(2012/10/18)
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- An efficient synthesis of 3-bromoflavones under solvent free conditions using grinding technique
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Selective bromination of 1-(2-hydroxyphenyl)-3-phenylpropane- 1,3-diones has been carried out with ammonium bromide and ammonium persulphate at room temperature using grinding technique under solvent free conditions to give 2-bromo derivatives which on cyclodehydration with p-toluenesulphonic acid under grinding conditions give 3-bromoflavones. Also, flavones on bromination using above mentioned conditions give 3-bromoflavones directly.
- Jakhar, Komal,Makrandi
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experimental part
p. 770 - 773
(2012/06/30)
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- A novel route to synthesis of flavones from salicylaldehyde and acetophenone derivatives
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Convenient, facile, and alternate synthesis of medicinally important flavones is reported. The 2-hydroxychalcones derived from condensation between acetophenones and salicylaldehyde, underwent oxidative cyclization on heating in the presence of catalytic iodine, generating diversified flavones under solvent-free conditions. Eleven compounds have been synthesized in good to excellent yields and their mechanism of formation is described.
- Sashidhara, Koneni V.,Kumar, Manoj,Kumar, Abdhesh
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p. 2355 - 2359
(2012/07/14)
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- A facile route to flavone and neoflavone backbones via a regioselective palladium catalyzed oxidative Heck reaction
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A straightforward and atom-economical base-free palladium-catalyzed regioselective direct arylation of coumarins and chromenones is devised. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and allows construction of various biologically important flavone and neoflavone backbones.
- Khoobi, Mehdi,Alipour, Masoumeh,Zarei, Samaneh,Jafarpour, Farnaz,Shafiee, Abbas
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p. 2985 - 2987
(2012/04/04)
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- Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: Efficient synthesis of flavones under mild reaction conditions
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Flavonoids are a class of natural products, found in a wide range of vascular plants and dietary components. Their low toxicity and extensive biological activities, including anti-cancer and anti-bacterial, have made them attractive candidates to serve as therapeutic agents for many diseases. Herein, we disclose a highly efficient synthetic method of CuI-catalyzed cascade oxa-Michael-oxidation, using chalcones as substrates, mediated by the ionic liquid [bmim][NTf2] at a low temperature. This efficient synthetic method has demonstrated high synthetic utility and can afford flavones in good to high yields (up to 98%).
- Du, Zhiyun,Ng, Huifen,Zhang, Kun,Zeng, Huaqiang,Wang, Jian
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p. 6930 - 6933
(2011/11/04)
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- Pd-carbene catalyzed carbonylation reactions of aryl iodides
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A series of carbene complexes [PdBr2(iPr 2-bimy)L] (C2-C13) with different types of co-ligands (L) have been tested for their catalytic activities in the carbonylative annulation of 2-iodophenol with phenylacetylene in DMF to afford the respective flavone 2a. Complex C12 with an N-phenylimidazole co-ligand showed the best activity and also afforded high yields when the substrate scope was extended to other aryl or pyridyl acetylenes. In addition, catalyst C12 was also efficient in the carbonylative annulation of 2-iodoaniline with acid chlorides giving the desirable 2-substituted 4H-3,1-benzoxazin-4-ones (4) in good yields. Additionally, this Pd-NHC complex also proved to be a very efficient catalyst for the hydroxycarbonylation of iodobenzene derivatives at low catalyst loading and under low CO pressure. These results demonstrate the versatility and efficiency of this phosphine-free Pd(ii)-NHC complex in different types of carbonylations of aryl iodides under mild conditions. The Royal Society of Chemistry 2011.
- Xue, Liqin,Shi, Lijun,Han, Yuan,Xia, Chungu,Huynh, Han Vinh,Li, Fuwei
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experimental part
p. 7632 - 7638
(2011/10/09)
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- Synthesis of chromones via palladium-catalyzed ligand-free cyclocarbonylation of o-iodophenols with terminal acetylenes in phosphonium salt ionic liquids
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(Chemical Equation Presented) The highly efficient and selective palladium-catalyzed ligand-free cyclocarbonylation reaction of o-iodophenols with terminal acetylenes and CO in the phosphonium salt ionic liquid,C 14H29(C6H13)3P +Br-, affords diversified chromones in good to excellent yields under atmospheric CO pressure. The ionic liquid, as the reactionmedium, enhances the efficiency of the cyclocarbonylation reaction.
- Yang, Qian,Alper, Howard
-
supporting information; experimental part
p. 948 - 950
(2010/04/30)
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- Oxidative rearrangements of 2'-hydroxychalcones with lh-l-hydroxy-5-methyl- l,2,3-benziodoxathiole 3,3-dioxide
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1H-l-hydroxy-5-methyl-l,2,3-benziodoxathiole 3,3-dioxide (HMBI) has been found to effect the direct conversion of 2'-hydroxychalcones with various B-ring substituents to isoflavones in moderate to good yield (34-83%) in methanol under reflux. The reduced byproduct of HMBI is easily recovered by aqueous extraction and can be recycled and reused with high efficiency. Previous reports of conversions of this type required the use of toxic thallium(III) salts or initial protection of the 2'-hydroxyl group.
- Justik, Michael W.,Zimmerman, Alyssa K.
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scheme or table
p. 67 - 71
(2010/03/03)
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- Enantioselective synthesis of chromanes by iridium-catalyzed asymmetric hydrogenation of 4H-chromenes
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Iridium complexes of chiral oxazoline-based P,N-ligands proved to be efficient catalysts for the enantioselective hydrogenation of 2-aryl- and 2-alkyl-4H-chromenes. The best results were obtained with a ligand derived from threonine (ThrePHOX), which induced ee values of 95% to >99% in the hydrogenation of 2-methyl-, 2-cyclohexyl- and various 2-aryl-substituted chromenes. Georg Thieme Verlag Stuttgart.
- Valla, Carine,Baeza, Alejandro,Menges, Frederik,Pfaltz, Andreas
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scheme or table
p. 3167 - 3171
(2009/06/17)
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- Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity relationships
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A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity.
- Cabrera, Mauricio,Simoens, Macarena,Falchi, Gabriela,Lavaggi, M. Laura,Piro, Oscar E.,Castellano, Eduardo E.,Vidal, Anabel,Azqueta, Amaia,Monge, Antonio,de Cerain, Adela Lopez,Sagrera, Gabriel,Seoane, Gustavo,Cerecetto, Hugo,Gonzalez, Mercedes
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p. 3356 - 3367
(2008/02/07)
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- Microwave enhanced palladium catalysed coupling reactions: A diversity-oriented synthesis approach to functionalised flavones
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Microwave enhanced diversity-oriented synthesis (MEDOS) using palladium catalysed protocols is introduced as a powerful new strategy for the synthesis of systematically modified small molecules and is highlighted by application to functionalised flavones. The Royal Society of Chemistry 2006.
- Fitzmaurice, Richard J.,Etheridge, Zac C.,Jumel, Emelie,Woolfson, Derek N.,Caddick, Stephen
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p. 4814 - 4816
(2007/10/03)
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- Benzoflavone activators of the cystic fibrosis transmembrane conductance regulator: Towards a pharmacophore model for the nucleotide-binding domain
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Our previous screen of flavones and related heterocycles for the ability to activate the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel indicated that UCCF-029, a 7,8-benzoflavone, was a potent activator. In the present study, we describe the synthesis and evaluation, using cell-based assays, of a series of benzoflavone analogues to examine structure-activity relationships and to identify compounds having greater potency for activation of both wild type CFTR and a mutant CFTR (G551D-CFTR) that causes cystic fibrosis in some human subjects. Using UCCF-029 as a structural guide, a panel of 77 flavonoid analogues was prepared. Analysis of the panel in FRT cells indicated that benzannulation of the flavone A-ring at the 7,8-position greatly improved compound activity and potency for several flavonoids. Incorporation of a B-ring pyridyl nitrogen either at the 3- or 4-position also elevated CFTR activity, but the influence of this structural modification was not as uniform as the influence of benzannulation. The most potent new analogue, UCCF-339, activated wild-type CFTR with a Kd of 1.7 μM, which is more active than the previous most potent flavonoid activator of CFTR, apigenin. Several compounds in the benzoflavone panel also activated G551D-CFTR, but none were as active as apigenin. Pharmacophore modeling suggests a common binding mode for the flavones and other known CFTR activators at one of the nucleotide-binding sites, allowing for the rational development of more potent flavone analogues.
- Springsteel, Mark F.,Galietta, Luis J. V.,Ma, Tonghui,By, Kolbot,Berger, Gideon O.,Yang, Hong,Dicus, Christopher W.,Choung, Wonken,Quan, Chao,Shelat, Anang A.,Guy, R. Kiplin,Verkman,Kurth, Mark J.,Nantz, Michael H.
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p. 4113 - 4120
(2007/10/03)
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- Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor
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A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands.
- Marder, Mariel,Zinczuk, Juan,Colombo, Maria I.,Wasowski, Cristina,Viola, Haydee,Wolfman, Claudia,Medina, Jorge H.,Ruveda, Edmundo A.,Paladini, Alejandro C.
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p. 2003 - 2008
(2007/10/03)
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- ONE-STEP CONVERSION OF FLAVANONES INTO ISOFLAVANONES: A NEW FACILE BIOMIMETIC SYNTHESIS OF ISOFLAVONES
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One-step chemical conversion of flavanones into isoflavones by use of thallium trinitrate (TTN) is reported, and the mechanism of a 2,3-aryl migration in this reaction is discussed in relation to in vivo rearrangement process of flavanone precursors in the isoflavone biosynthesis.
- Kinoshita, Takeshi,Ichinose, Koji,Sankawa, Ushio
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p. 7355 - 7356
(2007/10/02)
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- PHOTO-OXIDATIVE CYCLISATION OF 2'-HYDROXYCHALCONES LEADING TO FLAVONES INDUCED BY HETEROCYCLE N-OXIDES: HIGH EFFICIENCY OF PYRIMIDOPTERIDINE N-OXIDE FOR THE PHOTOCHEMICAL DEHYDROGENATION
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Irradiation of 2'-hydroxychalcones (3) with UV-visible light in the presence of heterocycle N-oxides such as pyrimidopteridine N-oxide (I) results in the formation of the corresponding flavones (4) and flavanones (5).The photooxidative cyclisation of (3) induced by (1) to give (4) most efficiently occurred among the heterocycle N-oxides examined and could be reasonably explained by considering an initial single-electron oxidation of (3) by (1) under the photochemical conditions and subsequent intramolecular cyclisation.
- Maki, Yoshifumi,Shimada, Kaoru,Sako, Magoichi,Hirota, Kosaku
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p. 3187 - 3194
(2007/10/02)
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- FLAVONOIDS, 40. SYNTHESIS OF 3-ALKYL- AND -ARYLTHIOFLAVANONES AND THEIR TRANSFORMATIONS INTO SULFUR-CONTAINING FLAVONOIDS
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trans-3-Mesyloxyflavanones 1 were converted into cis- and trans-3-(alkylthio)- and -(phenylthio)flavanones 2-4 by nucleophilic substitution reaction with thiols or thiolates.Flavanones 2-4 were useful intermediates in the synthesis of various sulfur-containing derivatives; flavanones, flavones and dihydrochalcones posessing alkyl- or arylthio, -sulfinyl and -sulfonyl group.Oxidation of cis- and trans- isomers of 4 led to completely different products.
- Patonay, Tamas,Patonay-Peli, Erzsebet,Litkei, Gyoergy
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p. 1827 - 1834
(2007/10/02)
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- FLAVONOIDS, XXXVII. RING CONTRACTION AND RING ENLARGEMENT REACTIONS WITH TRIMETHYLSILYL AZIDE IN THE FIELD OF FLAVONOIDS
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The reaction of flavanone with trimethylsilyl azide (TMSA) in trifluoroacetic acid (TFA) afforded by ring expansion, 2,3-dihydro-2-phenyl-1,4-benzoxazepin-5(4H)-one or 2,3-dihydro-2-phenyl-4H-tetrazolo-1,4-benzoxazepine.The same products could be isolated using sodium azide in TFA.An unknown intermediate of the Schmidt reaction was also isolated.Treatment of 2'-hydroxychalcone with TMSA or sodium azide in TFA resulted in isoflavone and trans-3-aminoflavanone.The reaction of 4-substituted 2'-hydroxychalcones with TMSA in dimethylformamide gave, with ring contraction, aurones and flavones.
- Litkei, Gy.,Patonay, T.
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- FLAVONOIDS, XXXVI REACTION OF 3-ALKYL- OR -ARYLSULFONYLOXYFLAVANONES WITH AMINES. SYNTHESIS OF 3-DIALKYLAMINOFLAVANONES
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Reactions of 3-alkyl- or -arylsulfonyloxyflavanones (1a-h) with primary and tertiary amines gave mixtures of the corresponding flavones (2a-d) and aurones (3a-d), while with secondary amines, in addition to 2 and 3, 3-dialkylaminoflavanones (6-9) were also obtained.The factors which determine the ratio of products are discussed.Treatment of the 3-dialkylaminoflavones 6a and 7 with DDQ gave 3-dialkylaminoflavanones (10, 11); treatment with alkali in methanol afforded 2-dialkylamino-2-benzylcoumaran-3-ones (12, 13).
- Patonay, T.,Litkei, Gy.,Bognar, R.
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p. 135 - 146
(2007/10/02)
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