Recent advances in the diversification of chromones and flavones by direct C H bond activation or functionalization

Tian, Shanghui; Luo, Tao; Zhu, Yan‐Ping; Wan, Jie‐Ping

doi:10.1016/j.cclet.2020.07.042

Cited by 55 publications

(12 citation statements)

References 92 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Other properties identified in chromone-based compounds are optical and chelating functions, which allow their wide application in the designation of organic materials. These biological activities are attributed to their structure and multiple substituents both on the heteroaryl ring and on the phenyl fragments of the central backbone [158] Overall, 11 flavones and chromones were obtained under these conditions, and although the yields were similar, the highest yield was achieved with the catalyst (P 5 W 30 ), with yields between 90 and 97%. Similar results were obtained using chloroform as reaction solvent and Preyssler heteropolyacids supported on silica (P 5 W 29 Mo/SiO 2 (50,40, and 30% active phase)).…”

Section: Flavones and Formylchromonesmentioning

confidence: 92%

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

et al. 2021

View full text Add to dashboard Cite

Over the past two decades, polyoxometalates (POM) have received considerable attention as solid catalysts, due to their unique physicochemical characteristics, since, first, they have very strong Bronsted acidity, approaching the region of a superacid, and second, they are efficient oxidizers that exhibit rapid redox transformations under fairly mild conditions. Their structural mobility is also highlighted, since they are complex molecules that can be modified by changing their structure or the elements that compose them to model their size, charge density, redox potentials, acidity, and solubility. Finally, they can be used in substoichiometric amounts and reused without an appreciable loss of catalytic activity, all of which postulate them as versatile, economic and ecological catalysts. Therefore, in 2009, we wrote a review article highlighting the great variety of organic reactions, mainly in the area of the synthesis of bioactive heterocycles in which they can be used, and this new review completes that article with the contributions made in the same area for the period 2010 to 2020. The synthesized heterocycles to be covered include pyrimidines, pyridines, pyrroles, indoles, chromenes, xanthenes, pyrans, azlactones, azoles, diazines, azepines, flavones, and formylchromones, among others.

show abstract

Section: Flavones and Formylchromonesmentioning

confidence: 92%

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The other is direct derivatization of chromone skeletons. [ 5‐8 ] However, these methods are commonly single‐tasked, thus the obtained flavones and isoflavones are of limited structural diversity, which limits their broad applications. Therefore, it is highly desirable to develop general and efficient approaches for rapid assembly of structurally diversified flavones and isoflavones from readily available starting materials.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Diversity‐Oriented Synthesis of Flavones and Isoflavones via Palladium/Norbornene Cooperative Catalysis

Gao

Zhou

et al. 2022

Chin. J. Chem.

View full text Add to dashboard Cite

Flavones and isoflavones are recognized as privileged heterocyclic scaffolds for the preparation of bioactive compounds. Efficient methods to access these heterocycles are in urgent need. Herein, we report diversity-oriented synthesis of flavones and isoflavones from 3-iodochromones via palladium/norbornene cooperative catalysis. The success of this research relies on the use of a unique bridge-head ester modified norbornene derivative as the mediator. Salient features of this include readily available starting materials regarding 3-iodochromones, ortho-C-H arylating and alkylating reagents and ipso-terminating reagents, broad substrate scope, good chemoselectivity, good step-economy and scalability. A large number of structurally diversified flavones, isoflavones and 2,3-diarylated chromones can be quickly prepared in a predictable manner. As showcased by the efficient formal synthesis of umbralisib, this chemistry can be treated as another valuable addition to the toolbox of medicinal chemists.

show abstract

“…[1] Thus, it is no surprise that the functionalization of chromones has been an active area of research. [2] In this regard, the direct C5 functionalization is particularly valuable because 5-alkyl or alkenyl substituted chromones can be very often encountered as a structural moiety in numerous natural products and show promising applications in medicinal fields (Figure 1). [3] However, most functionalizations of chromones so far have been focused on the 2-or 3-position (a conjugated enone fragment), which is a reactive synthon commonly used for the production of more complex structural diversities.…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of 5‐Alkylated and 5‐Alkenylated Chromones via Catalytic C‐H Coupling of Chromones with Allyl Alcohols

Wang

Zhao

et al. 2021

Eur J Org Chem

View full text Add to dashboard Cite

Herein, we describe two types of C5 functionalization reactions of chromones with allyl alcohols. Diverse 5‐substituted chromones can be produced by modulating the catalysts in these reactions: Rh(III) results in the formation of 5‐alkylated chromones, and Ru(II) furnishes 5‐alkenylated products. We also achieve further functionalizations of these 5‐substituted chromones, which demonstrates the superiority of this method. Notable features of these new methods include readily available precursors, tunable reactivity, exclusive C5‐selectivity, and easy derivatization of products.

show abstract

Recent advances in the diversification of chromones and flavones by direct C H bond activation or functionalization

Cited by 55 publications

References 92 publications

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

Diversity‐Oriented Synthesis of Flavones and Isoflavones via Palladium/Norbornene Cooperative Catalysis

Selective Synthesis of 5‐Alkylated and 5‐Alkenylated Chromones via Catalytic C‐H Coupling of Chromones with Allyl Alcohols

Contact Info

Product

Resources

About