24258-66-0

Upstream product

• 2491-31-8 2-hydroxy-deoxybenzoin 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 129218-87-7 (Z)-1-acetoxy-1-(2-acetoxyphenyl)-2-phenylethene 
• 1431841-85-8 3-iodo-2-methyl-4H-chromen-4-one 
• 98-80-6 phenylboronic acid 
• 5751-48-4 2-methylchromone 
• 1300581-09-2 6-Bromo-2-methyl-3-phenyl-4H-chromen-4-one 
• 54981-34-9 1-(5-bromo-2-hydroxyphenyl)-2-phenylethanone 
• 103-82-2 phenylacetic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 108-95-2 phenol 
• 103-80-0 phenylacetyl chloride 
• 113180-52-2 2-[2-(2-Oxo-2-phenyl-acetyl)-phenoxy]-propionic acid 

Downstream Products

• 89295-98-7 2-methyl-3-phenyl-chromene-4-thione 
• 73023-22-0 2-(3-methyl-4-phenyl-isoxazol-5-yl)-phenol 
• 70148-32-2 2-methyl-isoflavone epoxide 
• 1300582-79-9 2-[(1H-benzo[d]imidazol-1-yl)methyl]-3-phenyl-4H-chromen-4-one 
• 1300582-80-2 2-[(4-methyl-1H-benzo[d]imidazol-1-yl)methyl]-3-phenyl-4H-chromen-4-one 
• 1300582-81-3 2-[(6-chloro-9H-purin-9-yl) methyl]-3-phenyl-4H-chromen-4-one 
• 1300582-87-9 2-((9H-Purin-6-ylthio)methyl)-3-phenyl-4H-chromen-4-one 
• 1300582-88-0 2-[(1H-Imidazol-1-yl)methyl]-3-phenyl-4H-chromen-4-one 
• 1300583-77-0 2-((4-Amino-3-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one 
• 1300583-78-1 2-((4-Amino-3-(3-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one 
• 1300583-87-2 2-((4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one 
• 1300583-98-5 2-((4-amino-3-(pyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one 
• 1300584-00-2 2-((4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one 
• 1300584-01-3 2-((4-amino-3-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one 

Relevant academic research and scientific papers

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

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.

Preparation method and application of flavone and isoflavone compound

The invention provides a preparation method of a flavone and isoflavone compound, wherein the reaction formula is defined in the specification. The preparation method specifically comprises the following steps: in an inert gas atmosphere, taking a compound as shown in a formula A, B and C as initial raw materials, carrying out a stirring reaction in a solvent H under the action of a palladium catalyst D, a phosphine ligand E, norbornene F and an alkali G, and separating to obtain the flavone and isoflavone compound M, J, K or L. According to the invention, the main raw materials involved in the method are all commercial reagents and are low in price, the catalyst is a norbornene derivative, and compared with a catalyst norbornene used in similar reactions in the prior art, the dosage of the norbornene derivative is greatly reduced, the preparation cost is reduced, and the method is suitable for industrial production. The invention also provides an application of the prepared flavone and isoflavone compound in the preparation of a umbralisib core skeleton.

An efficient one-pot synthesis of indanone fused heterocyclic compounds via SeO2/FeCl3 promoted intramolecular Friedel-Craft acylation reaction

Indanones have been shown to exhibit a broad range of biological activities. An efficient and straightforward synthetic method for generating indanone fused heterocyclic compounds which contains a unique tetracyclic isoflavone moiety was developed. This unprecedented one-pot route utilizes a wide spread of substrates through three-step tandem Riley oxidation/Friedel-Crafts reaction/oxidation with SeO2/FeCl3 in moderate yield. Moreover, some of the synthesized heterocyclic compounds have shown moderate anticancer activities.

Ac2O-Mediated Dearylacetylative Dimerization of 2-Arylacetyl-1-naphthols: Synthesis of Naphtho[1,2-b]furan-3-ones

A novel and efficient route for the synthesis of 2-Aryl-2-naphthyl naphtho[1,2-b]furan-3-ones is described via NaH/Ac2O-mediated dearylacetylative dimerization of 2-Arylacetyl-1-naphthols in refluxing THF under open-flask conditions. A plausibl

NOVEL KINASE MODULATORS

The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.

A novel synthesis of 2,3-disubstituted benzopyran-4-ones and application to the solid phase

The development of a novel synthesis of 2,3-disubstituted benzopyran-4- ones and application to the solid phase are reported. Following model studies using benzyl alcohol as a surrogate for polystyrene hydroxymethyl resin, we utilized our previously established traceless diisopropylsilyloxy tinker methodology to synthesize a small library of target benzopyranones in generally high yield and purity. (C) 2000 Elsevier Science Ltd.

Photolysis of 3-bromochroman-4-ones

Photolysis of 3-bromochroman-4-ones (1a-f) leads to debrominated chromanones (2a-f) and chromones (3a-f) as major products. Their formation is accounted for in terms of primary cleavage of the carbon halogen bond to give α-carbonyl radicals (I) and/or cations (II). In the case of the 2,2-disubstituted compounds (1d-f), intermediates (II) undergo rearrangement with 1,2-shift of the phenyl or benzyl substituent prior to deprotonation. Minor by-products are the pentacyclic pyrone (4e) or 2-methylchromone (3a) (starting from 1e and 1f, respectively).

New procedures for the preparation of isoflavones with unsubstituted ring A

Isoflavones with unsubstituted ring A have been synthesized either by the ring closure of 2-hydroxydeoxybenzoins or by the dehydroxylation of 7-hydroxyisoflavones. 7-Mercaptoisoflavones have also been prepared.

Influence of the β-Substitution on the Photochemistry of α,2-Diacetoxystyrenes. Irradiatin of Phenyl, Vinyl, and Benzyl Derivatives

β-Substitution shows a pronounced influence on the photochemistry of α,2-diacetoxystyrenes.As in the case of the parent compound, intramolecular cyclization with participation of the neighbouring 2-acetoxy group takes place upon irradiation of the enol esters 4a-c; however other processes are also observed, depending on the substrate.The phenyl derivative 4a gives the E isomer 7a and the phenanthrene 9.The vinyl derivative 4b also undergoes cis-trans isomerization and/or photooxidation, to afford 7b and 10.Finally, a 1,4-acyl migratin occurs in the benzyl derivative 4c, whereby the 1,4-diketone 12 is formed.

Intramolecular Ketene Cycloadditions. Synthesis of Isoflavones and 3-Aroylbenzofurans

The conversion of 2-(carboxyalkoxy)benzils to the corresponding phenoxyketenes to an intramolecular ketene cycloaddition to ultimately yield isoflavones and/or 3-aroylbenzofurans.The ketenes may be generated by the classical dehydrochlorination of the acid chloride or by using Perkin reaction conditions, sodium acetate in refluxing acetic anhydride.The initial cycloaddition products are the corresponding β-lactones, which may decarboxylate to the isolated isoflavones and/or 2-aroylbenzofurans.The product distributions are dependent upon the substitution pattern in the orginal benzil acids.