1148-48-7Relevant academic research and scientific papers
Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization
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
, p. 14000 - 14006 (2021/04/22)
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.
Rh(III)-Catalyzed Aldehydic C?H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides
Xu, Guo-Dong,Huang, Kenneth L.,Huang, Zhi-Zhen
supporting information, p. 3318 - 3323 (2019/06/25)
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.).
An efficient tandem synthesis of chromones from: O -bromoaryl ynones and benzaldehyde oxime
Zhang, Jing-Wen,Yang, Wan-Wan,Chen, Lu-Lu,Chen, Pei,Wang, Yan-Bo,Chen, Dan-Yun
, p. 7461 - 7467 (2019/08/20)
An effective transition-metal-free strategy was developed for the preparation of chromones from o-bromoaryl ynones and benzaldehyde oxime through sequential C-O bond formation. This cyclization reaction could well tolerate a wide range of functional groups, and the corresponding chromones were given in moderate to excellent yields. Mechanistically, benzaldehyde oxime as a hydroxide source and 1,3-diketone derivatives as reaction intermediates were involved in this transformation.
Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides
Cheng, Kang,Chen, Jinkang,Jin, Licheng,Zhou, Jian,Jiang, Xinpeng,Yu, Chuanming
, p. 392 - 398 (2019/09/03)
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.
Green and efficient synthesis of flavones and chromones using heteropolyacids as catalyst in glycerol
Migliorero, María Belén Colombo,Palermo, Valeria,Durango, Edwin Alexis Alarcón,Holguín, Aída Luz Villa,Vázquez, Patricia Graciela,Sathicq, ángel Gabriel,Romanelli, Gustavo Pablo
, p. 826 - 832 (2018/11/06)
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.
Divergent synthesis of flavones and aurones via base-controlled regioselective palladium catalyzed carbonylative cyclization
Xu, Shan,Sun, Huaming,Zhuang, Mengyuan,Zheng, Shaohua,Jian, Yajun,Zhang, Weiqiang,Gao, Ziwei
, p. 264 - 270 (2018/05/04)
A regioselective approach for construction of 5-membered and 6-membered flavonoid is established by Pd catalyzed carbonylative cyclization of 2-iodophenol with terminal alkynes using different amine bases under mild reaction condition. The catalytic experiments found that piperazine preferentially accelerate 6-endo cyclization, and triethylamine mediated Pd catalyzed 5-exo cyclization. Under optimized reaction condition, Pd catalyzed carbonylative protocol successfully applied for the diverse structures of 39 examples in good to excellent yield and regioselectivity.
The acetoxy protection of the benzopyranone compound preparation acetylenic ketone method
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Page/Page column 0059-0062, (2017/08/19)
The invention discloses a method for preparing benzopyrone compounds through adopting acetoxy protected alkynyl ketone. The benzopyrone compounds are generated through a direct ring closure reaction of acetoxy protected alkynyl ketone at room temperature with piperazine as a catalyst. The method has the advantages of simple operation, no need of ligands, low price and small amount of the catalyst, stability of the catalyst to air and water, mild reaction conditions, short reaction time, low cost, high atom economy, extensive substrate applicability, and simple post-treatment and high yield of target products, and can be widely used to prepare natural products benzopyrone compounds.
A very simple solvent-free method for the synthesis of 2-arylchromones using KHSO4 as a recyclable catalyst
Pérez, María,Ruiz, Diego,Autino, Juan,Sathicq, Angel,Romanelli, Gustavo
, p. 551 - 555 (2016/06/01)
An efficient and solvent-free procedure for the synthesis of flavones using KHSO4 as a recyclable catalyst is described. The methodology represents an environmentally friendly process in comprehensive consideration compared with other catalytic systems listed in publications. This method provides a clean, simple, solvent-free reaction and useful alternatives to prepare flavones and chromones. The use of KHSO4 catalyst provides excellent yields, also leading to an easy separation and recovery of the catalysts, which allows both low environmental impact and low cost. Other green advantages of the method are the low formation of wastes and the replacement of corrosive, soluble mineral acids.
Mild and efficient organocatalytic method for the synthesis of flavones
Stanek, Filip,Stodulski, Maciej
supporting information, p. 3841 - 3843 (2016/08/02)
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.
Synthesis of flavones and γ-benzopyranones using mild sonogashira coupling and 18-crown-6 ether mediated 6-endo cyclization
Chuang, Da-Wei,El-Shazly, Mohamed,Balaji D., Barve,Chung, Yu-Ming,Chang, Fang-Rong,Wu, Yang-Chang
, p. 4533 - 4540,8 (2020/08/31)
An efficient method for the synthesis of flavones and γ- benzopyranones has been developed utilizing a mild Sonogashira coupling and 18-crown-6 ether mediated 6-endo cyclization of o-alkynoylphenyl acetates. By using this strategy, flavones and γ-benzopyranones bearing electron-donating groups, halogens, and simple alkyl substituents were synthesized in satisfactory yields. A facile, mild, and selective method for the synthesis of flavones and γ-benzopyranones is reported. o-Alkynoylphenyl acetates were obtained from either acyl chloride derivatives or substituted salicylates. Upon removing the acetate group, flavones and γ- benzopyranones were synthesized within 15 min with the aid of 18-crown-6 ether. A library of flavones and γ-benzopyranones was established. Copyright
