64353-75-9

Upstream product

• 103-82-2 phenylacetic acid 
• 156-87-6 propan-1-ol-3-amine 
• 72320-38-8 3-azidopropan-1-ol 
• 122-78-1 phenylacetaldehyde 
• 103-80-0 phenylacetyl chloride 
• 124932-16-7 N-(3-hydroxypropyl)-2-phenylacetamide 
• 140-29-4 phenylacetonitrile 
• 910794-36-4 N-(3'-bromopropyl)-2-phenylacetamide 

Downstream Products

• 1313272-91-1 methyl (E)-(6-oxo-8-phenyl-3,4-dihydro-2H-pyrrolo[2,1-b]-1,3-oxazin-7-ylidene)acetate 
• 1313273-04-9 dimethyl 2-(6-oxo-8-phenyl-3,4,6,7-tetrahydro-2H-pyrrolo[2,1-b]-1,3-oxazin-7-yl)-malonate 

Relevant academic research and scientific papers

Additive-free pd-catalyzed α-allylation of imine-containing heterocycles

An additive-free Pd-catalyzed α-allylation of different imino-group-ontaining heterocycles is reported. The activation of α-CH pronucleophiles (pKa (DMSO) > 25) occurs without the addition of strong bases or Lewis acids using only the Pd/Xantphos catalyst system. The reaction scope has been studied for various 5- and 6-membered nitrogen-containing heterocycles (yields up to 96%). Mechanistic investigations suggest an initial allylation of the imine-N followed by a Pd-catalyzed formal aza-Claisen rearrangement.

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.

CuCl-catalyzed radical cyclisation of N-α-perchloroacyl-ketene-N,S- acetals: A new way to prepare disubstituted maleic anhydrides

The copper-catalyzed radical cyclization (RC) of N-α-perchloroacyl cyclic ketene-N,X(X=O, NR, S)-acetals was studied. While the RC of N-acyl ketene-N,O-acetals was unsuccessful, the 5-endo cyclization of the other ketene acetals provided much better results, with the following order of cyclization efficiency: hexa-atomic cyclic ketene-N,NR-acetalspenta-atomic cyclic ketene-N,S-acetalshexa-atomic cyclic ketene-N,S-acetals. Invariably the catalytic cycle begins with the formation of a carbamoyl methyl radical. This leads to a cascade of reactions, including a radical polar crossover step, which ends with the formation of the maleimide nucleus, or precursors of this. Products from the RC of the hexa-atomic cyclic ketene-N,S-acetals, were efficiently transformed into disubstituted maleic anhydrides.

Efficient oxidative conversion of aldehydes to 2-substituted oxazolines and oxazines using (diacetoxyiodo)benzene

An efficient synthesis of 2-substituted oxazolines from aldehydes and 2-amino alcohol using (diacetoxyiodo)benzene as an oxidant, is reported. (Diacetoxyiodo)benzene acts as a mild dehydrogenating agent to convert the initially formed oxazolidine from ald

One-step conversion of aldehydes to oxazolines and 5,6-dihydro-4H-1,3-oxazines using 1,2- and 1,3-azido alcohols

The reactions of 1,2- and 1,3-hydroxy azides with aldehydes under acidic conditions were examined. A variety of Lewis acids were examined, of which BF3·OEt2 was found the most convenient. Trimethylsilyl ether derivatives of the alcohols could also be reacted using trimethylsilyl triflate as the promoter. Twenty-five examples that proceed in moderate to quantitative yields are reported.

A simple synthesis of Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and 2-substituted benzoxazoles

Carboxylic acids react readily at 0° ← + 24°C with amino alcohols, amino mercaptans and o-aminophenols in the presence of triphenylphosphine- or tributylphosphine dichloride (generated in situ from the reaction of the phosphines with hexacholoroethane or CCl4) and triethylamine in acetonitrile to form the corresponding Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and 2-substituted benzoxazoles in one reaction step in yields of up to 80%.

A SIMPLE SYNTHESIS OF Δ2-OXAZOLINES, Δ2-OXAZINES, Δ2-THIAZOLINES AND Δ2-IMIDAZOLINES

Carboxylic acids react with amino alcohols, amino mercaptans or diamines in the presence of triphenylphosphine, CCl4 and tert. bases to afford in 50-75percent yield the corresponding Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and Δ2-imidazolines.