120185-88-8

Upstream product

• 49619-82-1 3-bromo-4H-chromen-4-one 
• 24067-17-2 4-nitrophenylboronic acid 
• 96982-67-1 dibutyl p-nitrophenylboronate 
• 99-81-0 4-Nitrophenacyl bromide 
• 90-02-8 salicylaldehyde 
• 636-98-6 p-nitrobenzene iodide 
• 3034-09-1 4'-nitroflavanone 

Downstream Products

• 297163-64-5 3-(4-amino-phenyl)-chromen-4-one 

Relevant academic research and scientific papers

Novel synthesis of 3-phenyl-chromen-4-ones using n-heterocyclic carbene as organocatalyst: An efficient domino catalysis type approach

Herein is reported a simple and efficient synthesis of isoflavones starting from various substituted phenacyl bromides and salicylaldehydes in presence of NHC. The mechanism involved domino catalysis type approach with consumption and regeneration of catalyst in two catalytic cycles. This method proved to be very lucrative and gives very good yield. The method described here represents an environmentally benign alternative to classical approach.

Structural studies on bioactive compounds. 40.1 synthesis and biological properties of fluoro-, methoxyl-, and amino-substituted 3-phenyl-4H-1-benzopyran-4-ones and a comparison of their antitumor activities with the activities of related 2-phenylbenzothiazoles

A new series of fluoro-, methoxyl-, and amino-substituted isoflavones have been synthesized as potential antitumor agents based on structural similarities to known flavones and isoflavones (quercetin and genistein respectively) and antitumor 2-phenylbenzothiazoles. Target compounds were synthesized using palladium-catalyzed coupling methodologies to construct the central aryl carbon-carbon single bond. The new isoflavone derivatives were tested for in vitro activity in human breast (MDA-MB-468 and MCF-7) and colon (HT29 and HCT-116) cancer cell lines. Low micromolar GI50 values were obtained in a number of cases, with the MDA-MB-468 cell line being the most sensitive overall. Notably, significant potentiation of growth inhibitory activity (GI50 1 μM for 12d, 12f, 12h, 12k, 121, 12o but not the methylene-bridged derivative 12i) was observed when MDA-MB-468 cells were co-incubated with TBDD, a powerful inducer of cytochrome P450 (CYP)-1A1 activity, suggesting that isoflavone derivatives can act as substrates for CYP1A1 bioactivation.

A general method for the synthesis of isoflavones by oxidative rearrangement of flavanones using thallium (III) perchlorate

Oxidation of flavanones with thallium(III) perchlorate in acetonitrile or dimethoxyethane leads to 2,3-aryl migration providing a general method for the synthesis of isoflavones having electron relasing as well as electron withdrawing substituents at C2-aryl ring and the mechanism in relaltion to in vivo is discussed.

Oxidation of Flavanones using Thallium(III) Salts: A New Route for the Synthesis of Flavones and Isoflavones

When treated with thallium(III) acetate in acetic acid or acetonitrile, flavanones undergo facile dehydrogenation to afford flavones whereas, upon treatment with thallium(III) toluene-p-sulfonate or thallium(III) nitrate in propionitrile or acetonitrile, respectively, they undergo oxidative 2,3-aryl migration to give isoflavones in high yield.

Novel Synthesis of Isoflavones by the Palladium-Catalyzed Cross-Coupling Reaction of 3-Bromochromones with Arylboronic Acids or Its Esters

The synthesis of isoflavone derivatives by means of palladium-catalyzed cross-coupling reaction between 3-bromochromones and arylboronic acids or its butyl esters is described.