Ruthenium-Catalyzed C–H Activation of Salicylaldehyde and Decarboxylative Coupling of Alkynoic Acids for the Selective Synthesis of Homoisoflavonoids and Flavones

Raja, Gabriel Charles Edwin; Ryu, Ji Yeon; Lee, Ji Min; Lee, Sunwoo

doi:10.1021/acs.orglett.7b03325

Cited by 43 publications

(33 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2017, Lee’s research group exploited [Ru( p -cymene) 2 Cl 2 ] 2 to promote the C–H activation of salicylaldehyde 94 and trigger decarboxylative coupling with alkynoic acids 95 to reach obtain flavonoids 96, 97 ( Scheme 40 ) [ 101 ].…”

Section: Quercetin and Luteolinmentioning

confidence: 99%

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

2021

View full text Add to dashboard Cite

The outbreak of SARS-CoV-2 has drastically changed our everyday life and the life of scientists from all over the world. In the last year, the scientific community has faced this worldwide threat using any tool available in order to find an effective response. The recent formulation, production, and ongoing administration of vaccines represent a starting point in the battle against SARS-CoV-2, but they cannot be the only aid available. In this regard, the use of drugs capable to mitigate and fight the virus is a crucial aspect of the pharmacological strategy. Among the plethora of approved drugs, a consistent element is a heterocyclic framework inside its skeleton. Heterocycles have played a pivotal role for decades in the pharmaceutical industry due to their high bioactivity derived from anticancer, antiviral, and anti-inflammatory capabilities. In this context, the development of new performing and sustainable synthetic strategies to obtain heterocyclic molecules has become a key focus of scientists. In this review, we present the recent trends in metal-promoted heterocyclization, and we focus our attention on the construction of heterocycles associated with the skeleton of drugs targeting SARS-CoV-2 coronavirus.

show abstract

Section: Quercetin and Luteolinmentioning

confidence: 99%

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

2021

View full text Add to dashboard Cite

show abstract

“…In 2017, our group reported that a Ru-catalyzed decarboxylative coupling of arylpropynoic acids and salicylaldehyde formed homoisoflavonoids (in DMSO solvent) and flavones (in tert-amyl alcohol solvent) (Scheme 31). 36 It was observed that 2 equivalents of salicylaldehyde reacted with the alkynoic acid to give homoisoflavonoids. Chalcone is an intermediate in the formation of both products.…”

Section: Scheme 30 Coupling With Hypervalent Iodine Reagentsmentioning

confidence: 99%

Recent Advances in Decarboxylative Reactions of Alkynoic Acids

Idris

Lee

2020

Synthesis

Self Cite

View full text Add to dashboard Cite

Alkynoic acids have been widely employed as alkyne and alkene sources in decarboxylative reactions. Alkynoic acid coupling leads to the formation of direct coupling products and cyclized products through sequential reactions. Moreover, homocoupling and multicomponent reactions have been developed. The decarboxylative addition of alkynoic acids generates the corresponding alkene products. A number of synthetic methods are utilized for the preparation of arylpropynoic acids including the Sonogashira coupling and the carboxylation of terminal alkynes. Recently, the use of decarboxylative halogenations has also been reported. This review covers decarboxylative reactions of alkynoic acids reported between 2013 and 2019; further, it is divided into several sections according to the type of reaction.1 Introduction2 Direct Coupling3 Sequential Reactions4 Homocoupling5 Multicomponent Reactions6 Addition7 Halogenations8 Synthesis of Alkynoic Acids9 Conclusion

show abstract

“…In a serendipitous discovery, Lee and co-workers developed an interesting ruthenium-catalyzed synthesis of 2-arylhomo-isoflavonoid 179 scaffolds by reacting salicylaldehyde and alkynoic acids via C-H activation, as depicted in Scheme 6. 99 The reaction is proposed to proceed via initial formation of chalcone 175 that undergoes intramolecular cyclization to provide the flavonoid intermediate 176 .…”

Section: Biological Activities Of Hifsmentioning

confidence: 99%

Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities, and Synthesis (Part II)

Abegaz

Kinfe

2019

Natural Product Communications

View full text Add to dashboard Cite

This review documents all the new homoisoflavonoids (HIFs) that have been reported since 2007, whose total number has grown from 159 in 2007 to 295 at the present time. This review contains their structures, biological sources, plant parts they are obtained from, and, if reported, their optical rotations and melting points. The same classification is followed as an earlier review to ease reference to both reviews. This review takes note of the recent revision of plant families that were known to contain HIFs that have now been merged into one big family, Asparagaceae. Homoisoflavonoids also occur in Fabaceae and others. Two taxa, Ophiopogoan japonicus (Asparagaceae) and Caesalpinia sappan (Fabaceae), have been the source of many HIFs. These are briefly summarized. The biological properties of HIFs are also reviewed under the topics such as antioxidant, anti-inflammatory, antimicrobial, antidiabetic, and cytotoxic. The review also surveys the total synthesis of natural HIFs. All new compounds are classified and tabulated following the same style as the previous review. Dedicated to Professor Andrew Paul Krapcho on the occasion of his 87th Birthday.

show abstract

Ruthenium-Catalyzed C–H Activation of Salicylaldehyde and Decarboxylative Coupling of Alkynoic Acids for the Selective Synthesis of Homoisoflavonoids and Flavones

Cited by 43 publications

References 34 publications

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

Recent Advances in Decarboxylative Reactions of Alkynoic Acids

Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities, and Synthesis (Part II)

Contact Info

Product

Resources

About