- Novel Bifunctionalization of Activated Methylene: Base-Promoted Trifluoromethylthiolation of β-Diketones with Trifluoromethanesulfinyl Chloride
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A novel bifunctionalization of activated methylene was achieved successfully through the base-promoted trifluoromethylthiolation of β-diketones or β-ketoesters with trifluoromethanesulfinyl chloride. A series of α-trifluoromethylthiolated α-chloro-β-diketones and α-chloro-β-ketoesters were obtained in moderate to good yields under mild conditions. When β-diketones containing a phenyl group with a hydroxyl or amino substituent at the ortho position were used as substrates, intramolecular trifluoromethylthiolation/cyclization reaction took place to give the corresponding cyclic products. Furthermore, the protocol could be extended to perfluoroalkylthiolation with the sodium perfluoroalkanesulfinate/POCl3 system. On the basis of experimental results, plausible mechanisms are proposed.
- Sun, Dong-Wei,Jiang, Min,Liu, Jin-Tao
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supporting information
p. 10797 - 10802
(2019/07/03)
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- Rh(III)-Catalyzed Aldehydic C?H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides
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A novel aldehydic C?H functionalization reaction between salicylaldehydes and sulfoxonium ylides has been developed under rhodium(III) catalysis, affording coupling products in moderate to good yields. A plausible mechanism involving aldehydic C(sp2)?H activation by rhodium(III) and rhodium(III) catalyzed carbene insertion is also proposed. It was also found that the aldehydic C?H functionalization followed by dehydrative cyclization was able to produce flavonoids in one-pot. (Figure presented.).
- Xu, Guo-Dong,Huang, Kenneth L.,Huang, Zhi-Zhen
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supporting information
p. 3318 - 3323
(2019/06/25)
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- Rational design for multicolor flavone-based fluorophores with aggregation-induced emission enhancement characteristics and applications in mitochondria-imaging
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Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (φF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging.
- Liu, Liyan,Lei, Yaohui,Zhang, Jianhui,Li, Na,Zhang, Fan,Wang, Huaqiao,He, Feng
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- Transition-Metal-Free Photoinduced Intramolecular Annulation of 2,3-Di(hetero)arylchromen-4-one
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An efficient transition-metal-free photoinduced intracyclization of 4H-chromen-4-ones in EtOH-H2O (7:1, v/v) at ambient temperature for the construction of complicated fused-ring heteroaromatics is established. The reaction proceeds smoothly without requiring any catalysts/additives.
- Han, Jie,Wang, Tao,Liang, Yong,Li, Ying,Li, Chenchen,Wang, Rui,Feng, Siqi,Zhang, Zunting
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supporting information
p. 3552 - 3555
(2017/07/17)
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- Synthesis of novel fused chromone-pyrimidine hybrids and 2,4,5-trisubstituted pyrimidine derivatives via ANRORC rearrangement
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A facile and versatile procedure for the synthesis of functionalized novel 2,5-diphenyl-5H-chromeno[4,3-d]pyrimidin-5-ol and (2,4-diphenylpyrimidin-5-yl) (2-hydroxyphenyl) methanone has been described. The key step in the synthesis involves the ANRORC rea
- Sambaiah,Raghavulu,Shiva Kumar,Yennam, Satyanarayana,Behera, Manoranjan
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supporting information
p. 10020 - 10026
(2017/09/18)
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- Mild and efficient organocatalytic method for the synthesis of flavones
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A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.
- Stanek, Filip,Stodulski, Maciej
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supporting information
p. 3841 - 3843
(2016/08/02)
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- Intervention in cyclophosphamide induced oxidative stress and DNA damage by a flavonyl-thiazolidinedione based organoselenocyanate and evaluation of its efficacy during adjuvant therapy in tumor bearing mice
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A novel flavonyl-thiazolidinedione based organoselenocyanate compound was synthesized and established as nontoxic at the doses of 2.5 and 5 mg/kg b.w. in mice. Oral administration of the compound in combination with cyclophosphamide (CP) resulted in an im
- Roy, Somnath Singha,Chakraborty, Pramita,Bhattacharya, Sudin
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p. 195 - 209
(2014/01/23)
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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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body text
p. 770 - 773
(2012/06/30)
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- Investigation on the substitution effects of the flavonoids as potent anticancer agents: A structure-activity relationships study
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Three series of flavonoid analogues substituted with different aminomethyl substitutions at C-6, C-7, and C-8 were designed and synthesized for the structure-activity relationship studies as potent anticancer agents. The prepared analogues were evaluated for their in vitro inhibitory activity against the growth of the hepatic cancer cell lines HepG2 and SMMC-7721. Structure-activity relationships indicated that not only the compounds with amino methyl groups were more active than those without the groups in the same series but also the compounds substituted by aminomethyl groups at position C-8 were more active than those at positions C-6 and C-7.
- Wang, Xiao-Bing,Yang, Lei,Kong, Ling-Yi,Liu, Wei,Guo, Qing-Long
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p. 1833 - 1849,17
(2020/07/30)
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- Synthesis and properties of molecular probes for the rescue site on mutant cystic fibrosis transmembrane conductance regulator
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Cystic fibrosis is a genetic disease caused by mutations in the gene for the cystic fibrosis transmembrane conductance regulator (CFTR) protein. In vitro experiments have demonstrated that 4-methyl-2-(5-phenyl-1H-pyrazol-3-yl)phenol (VRT-532, 1) is able t
- Alkhouri, Bashar,Denning, Robert A.,Chiaw, Patrick Kim,Eckford, Paul D.W.,Yu, Wilson,Li, Canhui,Bogojeski, Jovanka J.,Bear, Christine E.,Viirre, Russell D.
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experimental part
p. 8693 - 8701
(2012/03/09)
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- New synthesis of 3-bromoflavones via bromination of 1-(2-hydroxyphenyl)-3- arylpropane-1,3-dione by CuBr2, and conversion into 3-aminoflavones
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A new synthesis of 3-bromoflavones from 1-(2-hydroxyphenyl)-3-arylpropane- 1,3-dione using CuBr2 is described. The usefulness of 3-bromoflavone as a precursor of 3-aminoflavone is also described. Copyright
- Miyake, Hideyoshi,Nishino, Shouko,Nishimura, Akinori,Sasaki, Mitsura
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p. 522 - 523
(2008/02/10)
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- Fast synthesis of some flavones under microwave irradiation
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Reactions under microwave irradiation occur under solvent free conditions. Such reactions occur in much shorter time than the usual ones. Fast synthesis of flavone from o-hydroxyacetophenone has been achieved in three steps under microwave irradiation.
- Mumtazuddin
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p. 835 - 837
(2007/10/03)
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- Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABAA receptor
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To further develop and evaluate a pharmacophore model previously proposed by Cook and co-workers (Drug Des. Discovery 1995, 12, 193-248) for ligands binding to the benzodiazepine site of the GABAA receptor, 40 new flavone derivatives have been synthesized and their affinities for the benzodiazepine site have been determined. Two new regions of steric repulsive interactions between ligand and receptor have been characterized, and the receptor region in the vicinity of 6- and 3′-substituents has been mapped out. 2′-Hydroxy substitution is shown to give a significant increase in affinity, which is interpreted in terms of a novel hydrogen bond interaction with the previously proposed hydrogen bond-accepting site A2. On the basis of the results of these studies and the refined pharmacophore model, 5′-bromo-2′-hydroxy-6-methylflavone, the highest affinity flavone derivative reported so far (Ki = 0.9 nM), was successfully designed. A comparison of the pharmacophore model with a recently proposed alternative model (Marder; et al. Bioorg. Med. Chem., 2001, 9, 323-335) has been made.
- Kahnberg, Pia,Lager, Erik,Rosenberg, Celia,Schougaard, Jette,Camet, Linda,Sterner, Olov,Nielsen, Elsebet ?stergaard,Nielsen, Mogens,Liljefors, Tommy
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p. 4188 - 4201
(2007/10/03)
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- Benzopyrans. Part 41.1 Reactions of 2-(2-dimethylaminovinyl)-lbenzopyran-4-ones with various dienophiles
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Dienamine 1 with W-phenylmaleimide and chromenone 14 as well as 15 produces, through initial [4 + 2]cycloaddition, xanthenones 10 and 18, respectively. Initial Michael addition of 1 to chromenones 14 and 16, and dimethyl acetylenedicarboxylate (DMAD), triggers the formation of xanthenone 19, 4-azaxanthenone 26 and substituted fumarate 49, respectively. Initial [2 + 2]cycloadducts of dienamines 1-3 with electrophilic acetylenes always undergo further transformations. Thus, 1 with DMAD, dibenzoylacetylene and ethyl propiolate (EP) ultimately gives xanthenones 33, 34 and 37, respectively, the latter being admixed with flavone 43. Enamine 2, cyclisable to xanthenone 11, gives 33 and 35 with DMAD, and 37 and 44 with EP. Reaction of 3 with DMAD affords 36 exclusively. The Royal Society of Chemistry 1999.
- Ghosh, Chandra Kanta,Bhattacharyya, Samita,Ghosh, Chandreyi,Patra, Amarendra
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p. 3005 - 3013
(2007/10/03)
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- Epoxidation of Flavones by Dimethyldioxirane
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The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported.These labile epoxides were isolated and completely characterized by UV, IR, 1H and 13C NMR, MS, and C,H analyses.Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n.Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f, as a mixture of cis and trans isomers.
- Adam, Waldemar,Golsch, Dieter,Hadjiarapoglou, Lazaros
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p. 7292 - 7297
(2007/10/02)
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- PHOTOLYSIS OF CYCLIC ACETALS OF ARYL BENZOYLACETATES AS THE KEY STEP IN A NEW SYNTHESIS OF FLAVONES
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Although the yields found for the photo-Fries rearrangement of the aryl benzoylacetates 1 are poor, blocking of the carbonyl group, as in the related acetal derivatives 3, results in a substantial preparative improvement.Thus, the o-hydroxydibenzoylmethanes 2 are obtained from 1 with an average yield of 18percent, while the corresponding acetals 4 are obtained from 3 with an average yield of 58 percent.Compounds 4 are efficiently converted into flavones 8 by means of wet silica gel, through hydrolysis of the acetal moiety and subsequent cyclization of the resulting o-hydroxydibenzoylmethanes 2.
- Garcia, Hermenegildo,Iborra, Sara,Miranda, Miguel A.,Primo, Jaime
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p. 2511 - 2517
(2007/10/02)
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