Fast and efficient synthesis of flavanones from cinnamic acids

Bedane, Kibrom Gebreheiwot; Majinda, Runner R. T.; Masesane, Ishmael B.

doi:10.1080/00397911.2016.1228110

Cited by 5 publications

(3 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…At this point we suspected that the proven solvent for the first step of the microwave promoted tandem sequence, N,N ‐diethylaniline, is less suitable for the second step, the oxa‐Michael addition. In previous reports on the synthesis of simple flavanones from chalcones polar‐protic solvents, in particular methanol, have been used, either in combination with a base [ 26 ] or with an acid. [ 23 ] For these reasons a modification of the one‐pot sequence by a solvent switch between the reaction steps was investigated: removal of N,N ‐diethylaniline after the first period of microwave irradiation was accomplished by extraction with diluted hydrochloric acid.…”

Section: Resultsmentioning

confidence: 99%

8‐Prenylflavanones through Microwave Promoted Tandem Claisen Rearrangement/6‐endo‐trig Cyclization and Cross Metathesis

2020

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

8‐Prenylflavanones through Microwave Promoted Tandem Claisen Rearrangement/6‐endo‐trig Cyclization and Cross Metathesis

2020

View full text Add to dashboard Cite

show abstract

“…A base-mediated internal Michael reaction of the chalcones of type 100 gave the corresponding flavanones of type 101 in 87-93% yields (Scheme 10). 71 This last step of the synthesis is not significantly affected by the substituents on the phenol.…”

Section: Methodsmentioning

confidence: 98%

An account of organic chemistry research in Botswana

Singh¹,

Majinda²,

Masesane³

2022

Arkivoc

Self Cite

View full text Add to dashboard Cite

The present paper gives an account of research in different areas of organic chemistry carried out at the University of Botswana. It describes the results of phytochemical investigations carried out on eight species of genus Erythrina. Several new alkaloids and non-alkaloids have been isolated and screened for different biological activities. Physicochemical properties and fatty acids composition of some oils are described as well. The paper also documents some synthetic approaches to natural products and their derivatives, β-amino acids, β-lactams, 1,3,4-oxadiazolines, spirooxindole-2-azetidinones and spirooxindole-oxiranes. The synthetic approaches include the elaboration of the Diels-Alder product of furan and some dienophiles to give the natural product oryzoxymycin and cyclohexyl-β-amino acids. In addition, studies on synthesis of chromane/chromene ring systems are summarized. The application of α-diazoketones and ethyl diazoacetate in the synthesis of βlactams, 1,3,4-oxadiazoline, spirooxindole-2-azetidinones, and spirooxindole-oxiranes is described. Some oxidative, reductive, and other reactions of β-lactams are discussed. In the green chemistry domain, results on grinding-induced synthesis of benzoxazines and microwave-assisted synthesis of benzil diimines are presented. Bis(acetylacetonato)copper(II)-catalyzed oxidation reactions of hydrazones and the sec-alcoholic group of benzoins to azines and 1,2-diketones, respectively, are described. In addition, the PdCl2-catalyzed transfer hydrogenation of alkenes to alkanes in the presence Zn powder is accounted.

show abstract

“…A number of these methods have been reported in literature. 5,6 Here, we report the acid-promoted reactions of phenols and ethyl phenylpropiolate as a possible synthetic route to neoflavones or/and flavones. The theoretical basis of using the acid-mediated reaction of phenols and ethyl phenylpropiolate is summarized in scheme 1.…”

Section: Introductionmentioning

confidence: 99%

BF3OEt2 and MeSO3H-Promoted reactions of phenols and ethyl phenylpropiolate as a synthetic routes to neoflavones and a potential route to flavones

Masesane¹,

Majinda²,

Kgakatsi³

2022

Arkivoc

Self Cite

View full text Add to dashboard Cite

The BF3.OEt2 and MeSO3H-promoted reactions of phenols and ethyl phenylpropiolate to give neoflavones in 17-96% and flavones in 0-25% yield are described. In general, phenols with activating substituents favor the formation of neoflavones under both BF3.OEt2 and MeSO3H-promoted reaction conditions. Phenol and p-Chlorophenol reacted with ethyl phenylpropiolate under the MeSO3H-promoted reaction conditions to give close to 1:1 mixtures of the corresponding neoflavones and flavones.

show abstract

Fast and efficient synthesis of flavanones from cinnamic acids

Cited by 5 publications

References 28 publications

8‐Prenylflavanones through Microwave Promoted Tandem Claisen Rearrangement/6‐endo‐trig Cyclization and Cross Metathesis

8‐Prenylflavanones through Microwave Promoted Tandem Claisen Rearrangement/6‐endo‐trig Cyclization and Cross Metathesis

An account of organic chemistry research in Botswana

BF3OEt2 and MeSO3H-Promoted reactions of phenols and ethyl phenylpropiolate as a synthetic routes to neoflavones and a potential route to flavones

Contact Info

Product

Resources

About