25755-82-2

Upstream product

• 5868-55-3 (3-p-tolyl-isoxazol-5-yl)-boronic acid 
• 27835-00-3 ethyl (4-methylbenzoyl)acetate 
• 124-38-9 carbon dioxide 
• 2089-33-0 4-methylacethophenone oxime 
• 1227841-23-7 (E)-4-methylbenzaldehyde O-3-(4-methylphenyl)propioloyl oxime 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 122-00-9 para-methylacetophenone 
• 616-38-6 carbonic acid dimethyl ester 
• 22027-51-6 3-oxo-3-p-tolyl-propionic acid methyl ester 
• 13820-14-9 4-methylbenzonitrile oxide 
• 441285-82-1 (Z)-3-amino-3-p-tolylacrylic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 104-85-8 para-methylbenzonitrile 

Downstream Products

• 65927-00-6 5-chloro-4-dichloromethyl-3-p-tolyl-isoxazole 
• 7118-66-3 5-methyl-2-(4-methylphenyl)-1H-benzimidazole 
• 139436-60-5 6-methyl-2-p-tolylquinoxaline 
• 1792-41-2 2,5-dimethylbenzimidazole 
• 142335-30-6 7-Methyl-4-p-tolyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 7118-65-2 5-chloro-2-(p-tolyl)-1H-benzo[d]imidazole 
• 139436-64-9 6-chloro-2-(p-tolyl)quinoxaline 
• 2818-69-1 5-chloro-2-methyl-1H-benzimidazole 
• 142335-33-9 7-Chloro-4-p-tolyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 120893-29-0 4-p-Tolyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 120-03-6 2-(p-tolyl)-1H-benzimidazole 
• 17286-62-3 2-(4-methylphenyl)quinoxaline 
• 30196-30-6 3,3'-di-p-tolyl-2H,2'H-2,2'-bibenzo[b][1,4]thiazine 

Relevant academic research and scientific papers

Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3-Oxazin-6-One Derivatives

A palladium catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed. In the reaction, a cascade process involving ring-opening/cyclization was suggested. The reaction features high atomic economy due to no elimination of CO2 occurred. Moreover, products obtained demonstrate aggregation-induced emission properties with relatively high solid-state emission efficiencies. (Figure presented.).

Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones

A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.

Palladium catalyzed insertion reaction of isocyanides with 3-arylisoxazol-5(4 H)-ones: Synthesis of 4-aminomethylidene isoxazolone derivates

A palladium catalyzed insert reaction of isocyanides to 3-arylisoxazol-5(4H)-ones for the construction of 4-aminomethylidene isoxazolone derivates is reported. In this transformation, only the C-H bond of the methylene group was involved while the remaining ring structure was retained. In general, this work provided a new protocol for the synthesis of 4-aminomethylidene isoxazolones.

Atom-Economic Silver-Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones

An unprecedented silver-catalyzed difunctionalization of the isocyano group with cyclic oximes is described. This method allows efficient and atom-economic assembly of a vast array of structurally novel and interesting pyrimidinediones, and tolerates a range of functionalities. The resulting products can be easily converted into some useful compounds. Furthermore, the method can also be applied for the late-stage modification of a few biologically active molecules.

Reformatsky and Blaise reactions in flow as a tool for drug discovery. One pot diversity oriented synthesis of valuable intermediates and heterocycles

The application of Reformatsky and Blaise reactions for the preparation of a diverse set of valuable intermediates and heterocycles in a one-pot protocol is described. To achieve this goal, a greener activation protocol for zinc in flow conditions has been developed to introduce this metal efficiently into α-bromoacetates. The organozinc compounds were added to a diverse set of ketones and nitriles to obtain a wide range of functional groups and heterocyclic systems.

Base initiated aromatization/CO bond formation: A new entry to O-pyrazole polyfluoroarylated ethers

A base initiated intermolecular SNAr reaction of pyrazolones with polyfluoroarenes was developed. The process involved the isomerization aromatization of pyrazolone followed by the CO bond formation via the selective CF bond cleavage. With this strategy, a wide range of O-pyrazole polyfluoroarylated ethers bearing diverse functional groups were synthesized in mild to good yields. Additionally, our method was also applied to the isoxazol substrates.

Synthesis of novel isoxazole fused heterocycles

Condensation of 3-aryl-4-formyl isoxazoles with 1,2-diamines led to the formation of 3-aryl-(6,7-benzo-1,5-heptadiazino)(3,2-d)-isoxazoles or isoxazolo-[5,4-b]-benzodiazepines and 3,10-diaryl-6,7,14,15-tetrhydro-13 H,16H-diisoxazole-(4,5-b;4,5-l)(1,4,8,11)-tetra-aza-cyclo-tetra-deca-4, 14-diones, the novel seven-and 14-membered heterocyclic systems. Similar compounds are of great importance in medicinal chemistry.

Gold-catalyzed cyclization and subsequent arylidene group transfer of O-propioloyl oximes

Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 °C in the presence of Au(PPh3)NTf2 (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.

Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)

The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50s of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min.

Reactivity of p-phenyl substituted β-enamino compounds using k- 10/ultrasound. II [1]. Synthesis of isoxazoles and 5-isoxazolones

The condensation of 4-phenyl substituted β-enamino ketones 1a-d and β- enamino esters 5a-d with hydroxylamine hydrochloride using K-10 as the solid support under sonication was studied to evaluate the formation of isoxazole and 5-isoxazolone rings from β-enamino compounds with a substituted aromatic ring. Isoxazoles 2a-c, 3c-d and 5-isoxazolones 6a-c and 7a-d were obtained. The use of K-10/ultrasound in this reaction furnished novel results in some cases.