Regioselective Halogenation of 2<i>H</i>‐Chromenones Promoted by Oxone and NaX: A Facile Approach for the Preparation of Halochromenones and 2<i>H</i>‐Chromenone Natural Products

Vanammoole, Lakshmireddy; Rajkumar, Kommera; Kurma, Siva Hariprasad; Vaidya, Jayathirtha Rao; Raju, B. China

doi:10.1002/slct.202000908

Cited by 8 publications

(6 citation statements)

References 67 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The intermediates II-1, II-2, and II-3 were prepared by referring to the reported methods. 21,22 Instruments. The melting points of the compounds were tested on an X-4 melting point apparatus (Beijing Tech Instruments Company) without correction.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Design, Synthesis, and Biological Activities of Novel Coumarin Derivatives as Pesticide Candidates

Ma,

Wang,

Wang

et al. 2024

J. Agric. Food Chem.

View full text Add to dashboard Cite

Food security is an important issue in the 21st century; preventing and controlling crop diseases and pests are the key to solve this problem. The creation of new pesticides based on natural products is an important and effective method. Herein, coumarins were selected as parent structures, and a series of their derivatives were designed, synthesized, and evaluated for their antiviral activities, fungicidal activities, and insecticidal activities. We found that coumarin derivatives exhibited good to excellent antiviral activities against tobacco mosaic virus (TMV). The antiviral activities of I-1, I-2a, I-4b, II-2c, II-2g, II-3, and II-3b are better than that of ribavirin at 500 μg/mL. Molecular docking research showed that these compounds had a strong interaction with TMV CP. These compounds also showed broad-spectrum fungicidal activities against 14 plant pathogenic fungi. The EC 50 values of I-1, I-2a, I-3c, and II-2d are in the range of 1.56−8.65 μg/mL against Rhizoctonia cerealis, Physalospora piricola, Sclerotinia sclerotiorum, and Pyricularia grisea. Most of the compounds also displayed good insecticidal activities against Mythimna separata. Pesticide-likeness analysis showed that these compounds are following pesticide-likeness and have the potential to be developed as pesticide candidates. The present work lays a foundation for the discovery of novel pesticide lead compounds based on coumarin derivatives.

show abstract

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…The reagents were purchased from commercial sources and were used as received. The intermediates II-1 , II-2 , and II-3 were prepared by referring to the reported methods. , …”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Biological Activities of Novel Coumarin Derivatives as Pesticide Candidates

Ma,

Wang,

Wang

et al. 2024

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…Additional references cited within the supporting information. [21][22][23][24][25][26][27][28][29][30][31][32][33][34]…”

Section: Summary Information Summarymentioning

confidence: 99%

Visible‐Light Mediated Metal‐free Synthesis of 3‐Bromo Coumarins Using In situ Generated Transient Non‐Symmetric Bromoiodanes

et al. 2023

View full text Add to dashboard Cite

We report herein the in situ generated transient non‐symmetric bromoiodanes promoted regioselective intramolecular halocyclization of alkynoates for the first time under visible light irradiation enables the formation of 4‐aryl‐3‐bromocoumarin derivatives. Using this protocol, a broad range of valuable brominated coumarins can be synthesized in moderate to excellent yield using simple household CFL bulb as light source under photocatalyst free condition. In addition, preliminary control studies were conducted to gain more insights to propose the plausible reaction mechanism.

show abstract

“…Oxone® has been used for the oxidative bromination of double bonds, [86b,88] enones, [84g,88] (di)ketones, [85a,86a] ketene dithioacetals, [84h] nucleobases, [89] various carbocycles, both through ring bromination [84d–f,85a,b,87,90] as well as on the side chain through a radical pathway, [85c] and various heterocycles [84a,91] . Secondary alcohols 24 were converted into α ‐haloketones 25 , and triple bonds 26 into α , α ‐dihaloketones 27 with two or three equivalents of Oxone® and bromide (Scheme 6).…”

Section: Oxone® and Persulfatesmentioning

confidence: 99%

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

2022

View full text Add to dashboard Cite

Bromination of organic substances is still an important reaction in modern synthetic chemistry. In view of the increasing demand for sustainable synthetic chemistry, oxidative bromination can play an important role to avoid the use of hazardous molecular bromine (Br 2 ). In this review, a complete overview of the chemical oxidants will be provided which have been used for the electrophilic as well as radical brominations, starting from less hazardous bromide Br(À I); e. g., HBr or a bromide salt, with a focus on the differences caused by the choice of oxidant.

show abstract

Regioselective Halogenation of 2H‐Chromenones Promoted by Oxone and NaX: A Facile Approach for the Preparation of Halochromenones and 2H‐Chromenone Natural Products

Cited by 8 publications

References 67 publications

Design, Synthesis, and Biological Activities of Novel Coumarin Derivatives as Pesticide Candidates

Design, Synthesis, and Biological Activities of Novel Coumarin Derivatives as Pesticide Candidates

Visible‐Light Mediated Metal‐free Synthesis of 3‐Bromo Coumarins Using In situ Generated Transient Non‐Symmetric Bromoiodanes

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

Contact Info

Product

Resources

About