676348-63-3

Upstream product

• 2142-70-3 2-iodoacetophenone 
• 616-38-6 carbonic acid dimethyl ester 
• 79-20-9 acetic acid methyl ester 
• 609-67-6 2-Iodobenzoyl chloride 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 38330-80-2 monomethyl monopotassium malonate 
• 88-67-5 2-Iodobenzoic acid 
• 14452-30-3 3'-iodoacetophenone 
• 1829-28-3 ethyl 2-iodobenzoate 

Downstream Products

• 1439356-84-9 methyl 1-methyl-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate 

Relevant academic research and scientific papers

NON type chiral bisoxazoline ligand nd synthesis method and application thereof

The invention relates to an NON type chiral bisoxazoline ligand and a synthesis method and application thereof. The ligand has a bisoxazoline structure as shown in a general formula 1, the synthesis method of the NON type chiral bisoxazoline ligand comprises the following steps: taking an o-iodobenzoic acid compound as an initial raw material, performing acylating chlorination on a benzoisofuranylalkylene dicarboxylic acid skeleton prepared through multi-step reaction, performing condensation with chiral amino alcohol, and finally performing cyclization to obtain a ligand 1 which is used for catalytic synthesis of chiral fluorinated beta-ketone ester. Compared with the prior art, the synthesis method disclosed by the invention is simple and efficient, mild in synthesis condition and easy to operate and good in repeatability, and the corresponding metal complex shows good catalytic activity and stereoselectivity in the asymmetric fluorination reaction of beta-ketone ester.

Expanding the Boxmi Ligand Family: Synthesis and Application of NON and NSN Ligands

Two synthetic strategies for a new family of neutral NON ligands featuring a bis(oxazolinylmethylidene)isobenzofuran framework (boxman) are reported. A Pd-mediated cyclization reaction forming the isobenzofuran core constitutes the key reaction in the eight-step synthetic route to the nonbackbone-methylated target compound H,Rboxman. In contrast, the introduction of two additional methyl groups provides stereochemical control during backbone construction and thereby access to the methylated derivative Me,Rboxman, which was synthesized in five steps and improved yields. In addition, the synthetic sequence was transferred to the thio analogue, providing access to the NSN ligand H,Rboxmene. Subsequent complexation experiments with iron and cobalt chloride precursors afforded the four-coordinated chlorido complexes Me,RboxmanMCl2 (R = Ph, iPr; M = Fe, Co) and established the boxman family as trans-chelating, bidentate bis(oxazoline) ligands. Application of the latter in the nickel(II)- and zinc(II)-catalyzed α-fluorination of β-ketoesters and oxindoles (up to 98percent yield and 94percent ee) demonstrated their suitability for enantioselective catalysis.

Palladium-Catalyzed Asymmetric Intramolecular Reductive Heck Desymmetrization of Cyclopentenes: Access to Chiral Bicyclo[3.2.1]octanes

A palladium-catalyzed asymmetric reductive Heck reaction of unactivated aliphatic alkenes, with eliminable β-hydrogen atoms, has been realized for the first time. A series of optically active bicyclo[3.2.1]octanes bearing chiral quaternary and tertiary carbon stereocenters were obtained in good yields with excellent enantioselectivities, exhibiting good functional-group tolerance and scalability. Moreover, deuterated optically active bicyclo[3.2.1]octanes were also obtained in high efficiency.

PhIO/Et3N ? 3HF-Mediated Formation of Fluorinated 2H-Azirines via Domino Fluorination/Azirination Reaction of Enamines

A variety of enamine carboxylic esters and enaminones were converted to the biologically interesting fluorinated 2H-azirines through reactions with PhIF2 generated in situ by PhIO and Et3N ? 3HF in 1,2-dichroloethane, which features the hypervalent iodine reagents-mediated introduction of fluorine atom and formation of the 2H-azirine skeleton under metal-free conditions. The domino reaction is postulated to proceed via a PhIF2-mediated oxidative fluorination and a subsequent azirination of the fluorinated enamine intermediates. (Figure presented.).

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.

Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process

Substrates bearing both a β-ketoester moiety and a (het)aryl halide structure element were dimerized to 1-naphthols and related products in the presence of catalytic amounts of CuI in isopropanol. The reaction starts with an intermolecular C-arylation, which is followed by an intramolecular condensation. The final aromatization delivers the highly substituted products with yields up to 81%.

Transition metal-free one-pot synthesis of 2-substituted 3-carboxy-4-quinolone and chromone derivatives

A novel one-pot synthesis of the 2-substituted 3-carboxy-4-quinolone/ chromone derivatives from readily available 3-oxo-3-arylpropanoates and amides/acyl chlorides is reported, without any transition metal aid. The Royal Society of Chemistry 2013.

COMPOUNDS USEFUL AS AICARFT INHIBITORS

Compounds of the formula:(where R1, R2 and R3 are defined in the specification) are inhibitors of AICARFT. These compounds, as well as their pharmaceutically acceptable salts, solvents, prodrugs, and pharmaceutically active metabolites, are useful in pharmaceutical compositions for treating diseases such as cancer.