22908-29-8

Upstream product

• 2916-76-9 methyl (trimethylsilyl)acetate 
• 100-00-5 4-chlorobenzonitrile 
• 27888-12-6 dimethylthiocarbamoylsulfanyl-acetic acid methyl ester 
• 53088-68-9 methyl 3-chlorophenylacetate 
• 611-06-3 2,4-dichloronitrobenzene 
• 150746-76-2 tris(dimethylamino)sulfonium trimethylsilyldifluoride 
• 147124-31-0 2-(5-Chloro-2-nitro-phenyl)-malonic acid dimethyl ester 

Downstream Products

• 17630-75-0 5-chloro-indolin-2-one 
• 22908-28-7 (5-chloro-2-nitro-phenyl)-acetic acid 

Relevant academic research and scientific papers

A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles

A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C?C and the subsequent umpolung C?O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.

IMIDAZOLINYLMETHYL ARALKYLSULFONAMIDES

Compounds of the Formula: where R1-R6 are those defined herein and methods for producing the same. Also provided are pharmaceutical compositions comprising a Compound of Formula I and methods for their use as therapeutic agents.

A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction

An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1.Chloride as well as fluoride could be used as the leaving group in this reaction.However, the latter was prefered since it required milder conditions.Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides.The nonproteinogenic α-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary.The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.

A general oxindole synthesis

A general synthesis of indol-2(3H)-ones (oxindoles), was developed based on the addition of dimethyl malonate to commercially available halonitrobenzenes. The advantage of this route over many other oxindole syntheses was the regiochemical control of the substitution pattern on the aromatic ring.

Process of preparing nitrodihydroaryl carbonyl compounds

Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.

Nucleophilic Addition of Silyl Enol Ethers to Aromatic Nitro Compounds: Scope and Mechanism of Reaction

In sharp contrast to alkali-metal enolates, silyl enol ethers and ketene silyl acetals add to aromatic nitro compounds in the presence of a fluoride ion source to give the intermediate dihydroaromatic nitronates, which can be observed by NMR.In situ oxidation of the intermediate with bromine or DDQ yields α-nitroaryl carbonyl compounds in moderate-to-high yields.The reaction is applicable to alkyl-, alkoxy-, and halogen-substituted nitrobenzenes as well as to heterocyclic and condensed nitroaromatic compounds.While substitution ortho to the nitro group predominates with sterically undemanding silyl reagents, para-substitution products are exclusively obtained with bulky reagents.However, by blocking the para position with an appropriate group such as chlorine, the addition can be directed to the ortho position.Halogen atoms of halogenated nitroaromatics and p-nitrocumenyl chloride are not displaced in the reaction, suggesting the absence of radical ion intermediates.Dihydroaromatic nitro derivatives ca be isolated in some cases, such as anthracene and naphthalene systems which are less prone to rearomatize.

Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes with α-Substituted Nitriles and Esters. Direct α-Cyanoalkylation and α-Carbalkoxyalkylation of Nitroarenes

Carbanions generated from alkanenitriles bearing α-chloro, α-OR, or α-SR groups and from aliphatic esters bearing α-SR groups react with mononitroarenes to replace hydrogen atoms of the nitroaromatic ring ortho or para to the nitro group with α-cyanoalkyl or α-carbalkoxyalkyl substituents.The nucleophilic replacement of hydrogen with such carbanions proceeds faster than substitution of halogen ortho or para to the nitro group.

Nucleophilic Addition of Silyl Enol Ethers to Aromatic Nitro Compounds: A Facile Synthesis of α-Nitroaryl Carbonyl Compounds

Silyl enol ethers and silyl ketene acetals add to aromatic nitro compounds in the presence of fluoride ion sources (e.g. tris(dimethylamino)sulfonium difluorotrimethylsiliconate (TASF)) to give, after oxidation, α-nitroaryl carbonyl compounds.