7399-68-0

Usage

Chemical Family

2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazole belongs to the oxazole family of chemical compounds.

Usage in Organic Synthesis and Pharmaceutical Research

The compound is used in organic synthesis and pharmaceutical research due to its various biological activities.

Antimicrobial and Anti-inflammatory Properties

2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazole has antimicrobial and anti-inflammatory properties, making it a potential candidate for the development of new drugs.

Potential Role in the Treatment of Certain Diseases and Conditions

The compound has been studied for its potential role in the treatment of certain diseases and conditions, making it an important chemical for further research and development.

Upstream product

• 19117-21-6 1-(4-chlorobenzoyl)aziridine 
• 39083-13-1 4-chloro-N-(2-bromoethyl)benzamide 
• 124-41-4 sodium methylate 
• 1517-05-1 2-azidoethanol 
• 104-88-1 4-chlorobenzaldehyde 
• 51847-02-0 4-chloro-N-(2-chloroethyl)benzamide 
• 868-85-9 Dimethyl phosphite 
• 36926-21-3 4-chloro-N-(2-hydroxyethyl)benzothioamide 
• 67-64-1 acetone 
• 141-43-5 ethanolamine 
• 74-11-3 para-chlorobenzoic acid 
• 623-03-0 4-Cyanochlorobenzene 
• 5714-33-0 2-(2-mercaptoethyl)-aminoethanol 
• 36615-72-2 phenacylsulfonylacetic acid methyl ester 

Downstream Products

• 82891-89-2 2-<2-(methylthio)-4-chlorophenyl>-2-oxazoline 
• 82891-84-7 2-(4-propylphenyl)-4,5-dihydrooxazole 
• 126773-84-0 5-Bromo-2-(4-chlorophenyl)oxazole 
• 46047-24-9 2-(4-chlorophenyl)oxazole 
• 104-88-1 4-chlorobenzaldehyde 
• 1119513-01-7 bis-(2-[p-chlorophenyl]-2-oxazoline-κ1N) zinc(II) bromide 
• 1119512-94-5 bis-(2-[p-chlorophenyl]-2-oxazoline-κ1N) zinc(II) chloride 
• 80253-66-3 cyanomethyl 4-chlorobenzoate 
• 82891-93-8 2-(2-methyl-4-n-propylphenyl)-2-oxazoline 
• 82891-91-6 2-(2-methyl-4-chlorophenyl)-2-oxazoline 
• 126773-87-3 C₉H₅⁽²⁾HClNO 

Relevant academic research and scientific papers

Facile one-pot synthesis of 2-oxazoline

We developed a facile one-pot synthesis of 2-oxazolines from carboxylic acid and 2-chloroethyl isocyanate, involving amide bond formation and a following intramolecular cyclization using 4-dimethylaminopyridine as the catalyst. A large variety of functional groups are well tolerated by the mild reaction conditions to afford diverse 2-oxazolines in good to excellent yields. This reaction will keep the chirality of the isocyanate at position 1, the R2 substituted carbon. Microwave-assisted synthesis can further enhance the reaction yield and reduce the reaction time to 5 min. This method facilities the synthesis of 2-oxazolines for diverse applications, such as 2-oxazoline derived polymers and materials.

Rhodium(III)-Catalyzed Oxidative Cyclization of Oxazolines with Cyclopropanols: Synthesis of Isoindolinones

The synthesis of C3-substituted isoindolin-1-ones from oxazolines and cyclopropanols has been achieved with oxazoline as a bifunctional nucleophilic directing group. The reaction proceeds by the cleavage of three chemical bonds and allows the formation of three new chemical bonds, a C-N bond, a C-C bond, and a C-O bond, in a single step.

Mild, Selective Ru-Catalyzed Deuteration Using D2O as a Deuterium Source

A method for the selective deuteration of polyfunctional organic molecules using catalytic amounts of [RuCl2(PPh3)3] and D2O as a deuterium source is presented. Through variation of additives like CuI, KOH, and various amounts of zinc powder, orthogonal chemoselectivities in the deuteration process are observed. Mechanistic investigation indicates the presence of different, defined Ru-complexes under the given specific conditions.

Cu(II) immobilized on Fe3O4@Agarose nanomagnetic catalyst functionalized with ethanolamine phosphate–salicylaldehyde schiff base: A magnetically reusable nanocatalyst for preparation of 2-substituted imidazolines, oxazolines, and thiazolines

Herein we synthesized Cu(II) immobilized on Fe 3 O 4 @Agarose functionalized with ethanolamine phosphate–salicylaldehyde Schiff base (Fe 3 O 4 @Agarose/SAEPH 2 /Cu(II)) as a new and cost-effective nanomagnetic catalyst. The nanomagnetic catalyst was characterized by FT- IR, XRD, VSM, SEM- EDX, TEM, TGA, and ICP techniques and it was found that the particles were about 9–25 nm in size and spherical with entrapment of the Fe 3 O 4 particles in the hollow pore structure of the agarose. The prepared nanomagnetic catalyst showed excellent activity for preparation of 2-substituted imidazolines, oxazolines, and thiazolines. The catalyst is easy to prepare and exhibits higher catalytic activity than some commercially available copper sources. More importantly, this nanomagnetic catalyst can be easily recovered by using a permanent magnet and reused for at least seven cycles without significant deactivation.

A 2 - substituted oxazoline or 2 - substituted piperazine synthetic method (by machine translation)

The invention discloses a method for synthesizing 2 - substituted oxazoline or 2 - substituted oxazine new method, by nitrile and amino ethanol or 3 - amino - 1 - propanol as raw material, in the absence of solvent, can be used for the recycling of the sulfur to induce synthesis of 2 - substituted oxazoline and 2 - substituted piperazine. The method of the invention has low cost, simple reaction process, mild reaction conditions, the reaction time is short, the yield and the like, is suitable for the industrial generation. (by machine translation)

Highly efficient synthesis of β-nitrate ester carboxamides through the ring-opening of 2-oxazolines

A novel method for the synthesis of β-nitrate ester carboxamides using non-corrosive tert-butyl nitrite (TBN) as the nitro source and easily available oxygen as the oxidant has been developed. Variously substituted 2-oxazolines were efficiently ring-opened to deliver the corresponding products in excellent yields. Notably, this reaction provides fast access to pharmaceuticals such as nicorandil.

Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines

The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.

Willgerodt–Kindler reaction-driven one pot solventless entry to 2-oxazolines

We report an efficient and green protocol for the synthesis of 2-oxazolines by the reaction of aromatic nitriles with β-aminoalcohols using sulfur under solvent-free conditions. The reaction occurs via the Willgerodt-Kindler mechanism followed by transami

A Mild and Regioselective Route to Functionalized Quinazolines

A Rh-catalyzed ortho-amidation cyclocondensation sequence gave a range of 4-aminoquinazolines in high yield. The method features a remarkably mild C(sp2)-H activation step and can be exploited to rapidly access compounds with established biological activity.

An efficient one-pot synthesis of 2-oxazolines with molecular iodine under ultrasound irradiation

A series of 2-oxazolines were prepared by the condensation of aldehydes with 2-aminoethanol in the presence of molecular iodine and potassium carbonate in t-BuOH at 35-40 °C under ultrasound irradiation. The easy work-up procedure and moderate to good yie