- 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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- Method for synthesizing 2-aryl benzopyrone flavonoid derivatives
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The invention relates to a method for synthesizing 2-aryl benzopyrone flavonoid derivatives, and relates to a method for synthesizing a compound, the method for synthesizing 2-aryl benzopyrone flavonoid derivatives is suitable for the synthesis of 2-aryl benzopyrone flavonoid derivatives containing different substituents. The method aims to solve the technical problems of low yield, long reactionperiod, and complicated post-treatment and high operation difficulty of the existing synthesis method of the ketone flavonoid derivative. The method comprises the following steps of: 1, preparing beta-propanedione compounds; 2, preparing flavonoid compound 2-aryl benzopyranones. The method completes esterification and rearrangement in one step, which is simple and practical, reduces intermediate links of reaction, saves separation and purification of intermediate products, improves utilization rate of raw materials, reduces reaction temperature, shortens reaction time under microwave radiation, reduces solvent consumption, the post-treatment is relatively simple, the yield is relatively high and no by-products exist, and can also react in the presence of a small amount of water, the reaction is easy to operate, and the method is suitable for industrial production. The method belongs to the technical field of compound synthesis.
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Paragraph 0070; 0071; 0072
(2019/04/30)
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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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- Green and efficient synthesis of flavones and chromones using heteropolyacids as catalyst in glycerol
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Organic solvents are required to carry out most organic transformations, which cause environmental pollution because of their low volatility. Glycerol, a side product obtained from biodiesel production, has emerged as a friendly solvent due to its advantageous properties. In this paper, an efficient procedure for the synthesis of flavones and chromones, using heteropolyacids as recyclable catalyst and glycerol as the solvent, is presented. The use of heteropolyacids as catalysts allows for excellent yields, easy separation and recovery, low environmental impact, and low cost. Glycerol can also be readily recovered and used over again. In addition, the presented method provides other advantages such as the low formation of waste and the replacement of corrosive mineral acids.
- Migliorero, María Belén Colombo,Palermo, Valeria,Durango, Edwin Alexis Alarcón,Holguín, Aída Luz Villa,Vázquez, Patricia Graciela,Sathicq, ángel Gabriel,Romanelli, Gustavo Pablo
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p. 826 - 832
(2018/11/06)
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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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- A 7 - methoxy flavone preparation method (by machine translation)
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The invention discloses a 7 - methoxy flavone preparation method, which belongs to the field of chemical synthesis, the method comprising: in order to Paeonia suffruticosa Andr. (tree peony bark) phenol and benzoyl chloride as the raw material, in the presence of triethylamine base to carry out the esterification reaction, the reaction mixture after the reaction is finished by carrying out simple suction filtering to eliminate triethylamine hydrochloride, potassium tertiary butanol filtrate directly the reaction at room temperature, after the reaction is finished adding dibutyl tin oxide and to the reaction mixture liquid to heating reflux dehydration, to obtain 7 - methoxy flavone. The technical route has the route is short, simple and convenient operation, pollution-free, the dehydrating agent can be used in circulation, and easy for industrial production characteristics, is a very economic, simple preparation of 7 - methoxy flavone method. (by machine translation)
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- Convenient one-pot synthesis of chromone derivatives and their antifungal and antibacterial evaluation
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A one-pot method for the synthesis of chromone derivatives from the reaction of 2-hydroxyacetophenones with aliphatic or aromatic acid chlorides is reported. Esterification and Baker-Venkataraman rearrangement were promoted by t-BuOK, which was followed directly by acid-catalyzed cyclization in one pot. Some of 2-cyclohexyl- and 2-cyclohexylmethyl-substituted chromones displayed activity against plant pathogenic fungal strains. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Ghani, Sherif B. Abdel,Mugisha, Patrick J.,Wilcox, Juliet C.,Gado, Emad A. M.,Medu, Erere O.,Lamb, Andrew J.,Brown, Richard C. D.
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p. 1549 - 1556
(2013/05/22)
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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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- Assessment of antiplatelet activity of 2-aminopyrimidines
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A series of 4,6-diaryl-2-aminopyrimidines was developed as antiplatelet agents and their potency was evaluated by in vitro assay. Compound 14k was found to be two times more potent than aspirin. These encouraging results could be helpful for the development of new antiplatelet compounds.
- Giridhar, Rajani,Tamboli, Riyaj S.,Ramajayam,Prajapati, Dhaval G.,Yadav
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scheme or table
p. 428 - 432
(2012/07/03)
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- Design and synthesis of 3,5-diarylisoxazole derivatives as novel class of anti-hyperglycemic and lipid lowering agents
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We have designed 1,3-disubstituted-5-membered heteroaromatic ring system as a common core motif from known anti-hyperglycemic agents. Designed compounds were synthesized and screened for in vivo anti-hyperglycemic activity in sucrose loaded model (SLM), sucrose-challenged streptozotocin-induced diabetic rat model (STZ-S) as well as db/db mice model. Some of the synthesized compounds showed promising in vivo anti-hyperglycemic as well as moderate lipid lowering activity. Synthesized Compounds were screened in various in vitro models of type-2 diabeties such as DPP-4, PTP1B and PPARγ to know the mechanism of their anti-hyperglycemic action. None of the synthesized compounds showed DPP-4 inhibitory as well as PPARγ activity. These compounds have shown promising PTP-1B inhibitory activity there by revealing that compounds exhibit anti-diabetic activity by PTP1B pathway.
- Kumar, Atul,Maurya, Ram Awatar,Sharma, Siddharth,Ahmad, Pervez,Singh,Tamrakar,Srivastava, Arvind K.
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experimental part
p. 5285 - 5292
(2009/12/09)
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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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- New synthesis of 1,3-diarylpropane-1,3-diones
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1,3-Diarylpropane-1,3-diones have been synthesized by (i) UV irradiation and thermal rearrangement of o-aroyloxyacetophenones and (ii) microwave irradiation of aroyl chlorides and o-hydroyacetophenones.
- Bansal,Singh,Khanna
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p. 586 - 587
(2007/10/03)
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- A new metal complex promoted system for highly selective synthesis of 4H-chromen-4-ones (chromones)
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Co(III)(salpr)(OH), a six coordinate cobalt Schiff base complex, promotes the highly selective conversion of 1-(o-hydroxyaryl)-1,3-diketones to 4H-chromen-4-ones under neutral conditions.
- Nishinaga,Ando,Maruyama,Mashino
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p. 839 - 841
(2007/10/02)
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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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- Structural Studies on Bio-active Compounds. Part 12. Tautomerism and Conformation of Aryl-substituted 1-(2-Hydroxyphenyl)-3-phenylpropane-1,3-diones in the Solid Phase and in Solution
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The tautomerism of a series of aryl-substituted 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-diones has been studied in deuteriochloroform solution by 1H n.m.r. techniques and, in the case of 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione and 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione, in the solid state by X-ray crystallography.Of these compounds, most exist between 80 and 95percent in the enolised form in solution and 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione adopts this tautomer in the crystal.However, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione is present as the diketone in the solid phase and enolises very slowly in solution. 1-(6-Benzoyloxy-2-hydroxyphenyl)-3-hydroxy-3-phenylprop-2-en-1-one is shown by 1H n.m.r. spectroscopy possibly to adopt a 'coiled' conformation in solution in deuteriochloroform.
- Cunningham, Bernadette D. M.,Lowe, Philip R.,Threadgill, Michael D.
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p. 1275 - 1284
(2007/10/02)
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