74018-54-5

Upstream product

• 1073-06-9 3-fluorobromobenzene 
• 118559-32-3 4,4-dimethyl-2-(tri-n-butylstannyl)-2-oxazoline 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 456-48-4 3-Fluorobenzaldehyde 
• 106588-42-5 N-(2-methyl-3-hydroxypropyl)-3-fluorobenzamide 
• 455-38-9 3-fluorobenzoic acid 
• 104283-71-8 2-(3-Fluoro-phenyl)-4,4-dimethyl-oxazolidine 
• 1711-07-5 3-fluorobenzoyl chloride 

Downstream Products

• 853946-01-7 4-fluoro-3-(2-fluorophenyl)isobenzofuran-1(3H)-one 
• 135061-85-7 4,4-Dimethyl-2-(2-benzylseleno-3-fluorophenyl)-1,3,oxazoline 
• 111771-24-5 3-fluoro-2-<(5,6,7,8-tetrahydro-1-naphthalenyl)methyl>benzoic acid 
• 853946-02-8 1-(2-(2-fluorobenzyl)-3-fluorophenyl)ethanone 

Relevant academic research and scientific papers

Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines

A selective ortho,ortho’-functionalization of readily available aryl oxazolines by two successive magnesiations with sBu2Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62–99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 °C, 4 h) provided the corresponding nitriles (36 examples, 73–99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed.

Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.

Directed functionalization of halophenyl-2-oxazolines with TMPMgCl?LiCl

A variety of difunctionalized aryl-2-oxazolines were prepared from the reaction of halophenyl-2-oxazolines and TMPMgCl?LiCl to give an organomagnesium reagent, which was then treated with various electrophiles. The metalation step takes place under mild conditions, and this process al-lows for the isolation of the desired products in good yields. No isomeric or other benzyne-derived products were detected. The influence of the halogen substituents on the acidity of the aromatic hydrogen atoms was evaluated by using density functional theory (DFT) calculations.

NEW COMPOUNDS I/418

There is provided compounds of formula I, wherein R1 to R7 have meanings given in the description, which are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and ventricular arrhythmias.

Synthesis of symmetrical triarylphosphines from aryl fluorides and red phosphorus: Scope and limitations

The reaction of aryl fluorides with phosphide anion, generated in situ from the reduction of red phosphorus by lithium metal in liquid ammonia, gave symmetrical triarylphosphines in fair to good yields. Phosphonodiamide, sulfonamide, 2-oxazolyl, and nitrile groups were stable to the reaction conditions, while nitro and bromo substituents were not. para-Substituted aryl fluorides gave higher yields than meta-substituted aryl fluorides, and ortho-substituted aryl fluorides failed to react.

Peri Fluoro Steric Effects: Syntheses and Comparative Acid-Catalyzed Isomerization of the 8-, 9-, and 11-Fluoro-1,2,3,4-tetrahydro-7,12-dimethylbenzanthracenes to Exo Methylene Tautomers

Facile and regiospecific syntheses for 8-, 9-, and 11-fluoro-1,2,3,4-tetrahydro-7,12-dimethylbenzanthracenes (4, 5, and 7) from 5,6,7,8-tetrahydro-1-naphthaldehyde and the respective 2-(2-fluoro-6-iodophenyl)oxazoline 14, 2-(2-bromo-5-fluorophenyl)oxazoline 15, and 2-(3-fluorophenyl)oxazoline 16 are described.Comparative acid-catalyzed isomerization of these polycyclic aromatic hydrocarbons (PAH) to exo methylene tautomers in refluxing benzene is compared to our previously published studies employing the parent hydrocarbon 1 and the 5-, 6-, and 10-fluoro analogues(2, 3, and 6).The peri steric effect of 11-fluoro compound 7- was the most dramatic, providing 7-exo methylene isomer 45 in nearly quantitative yield.Substitution of fluorine at peri positions 6 and 8 afforded product ratios at equilibrium, whereas the 7-exo methylene tautomers (41 and 42) also were thermodynamically favored over the parent anthracene PAH or the respective 12-exo methylene isomers (48 and 49).Like the unsubstituted PAH 1, where fluorine does not occupy a peri position such as in the 9- and 10-fluoro species 5 and 6, no appreciable quantities of exo methylene tautomers were detected.Comparative ΔGo values for isomerization of 6-, 8-, and 11-fluoro isomers revealed that sandwiching the C12-CH3 group between the 11-fluoro and C1-CH2 functions in 7 and removing any possible 7-CH2-F interaction in exo methylene product 45 led to a relative relief in steric interaction of approximately 1 kcal/mol.

A NEW ROUTE TO 3-HYDROXYPHTHALIDES : APPLICATION TO THE SYNTHESIS OF RACEMIC DAUNOMYCINONE.

Lithiation (n-BuLi) of the (3'-methoxyphenyl) oxazoline (2a) occurs specifically at C2' and, following carboxylation (CO2/13CO2) and esterification, yields the phthalate derivative (e.g. 5a).Elaboration of the oxazoline-ring furnishes the related aldehyde