1190286-86-2

Upstream product

• 2393-23-9 4-methoxy-benzylamine 
• 536-74-3 phenylacetylene 
• 67-64-1 acetone 
• 591-50-4 iodobenzene 

Downstream Products

• 1316844-97-9 C₃₀H₃₉N₃O₅ 
• 1190287-00-3 (Z)-5-benzylidene-3-(4-methoxybenzyl)-4,4-dimethyloxazolidin-2-one 

Relevant academic research and scientific papers

Stereoselective amination: Via vinyl-silver intermediates derived from silver-catalyzed carboxylative cyclization of propargylamine

The stereoselective synthesis of aminovinyloxazolidinones based on the electrophilic amination of a vinyl-silver intermediate, generated by silver-catalyzed carbon dioxide incorporation on a propargyl amine, was achieved. The geometry of the aminated product was determined by a single crystal X-ray analysis and NOE measurement and it was elucidated that the geometry was proved to be opposite to the geometry predicted from the previous silver-catalyzed carbon dioxide fixation on a propargyl amine derivative. This unexpected stereoselectivity could be successfully explained by a radical mechanism. This journal is

Silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for stereoselective preparation of (E)-iodovinyloxazolidinones

The silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for the stereoselective synthesis of (E)-iodovinyloxazolidinones was developed. The silver-catalytic system could be applied to various propargylic amines to afford the corresponding iodovinyloxazolidinones in high yields. The structure of the oxazolidinone was confirmed by X-ray structure analysis to be the Eisomer for the geometry of the exo-olefin. The silver-catalyzed cyclization and replacement of silver with the iodine group in the intermediate were thought to be crucial steps.

Base-Promoted Carbonylative Cyclization of Propargylic Amines with Selenium under CO Gas-free Conditions

We report here a new carbonylative procedure for the cyclization of propargylic amines with elemental selenium (Se). By using tBuOK as the promoter, various 1,3-selenazolidin-2-ones were produced without the usage of toxic CO gas. Benzene-1,3,5-triyl triformate (TFBen) was employed as a safe and convenient CO surrogate here, and a broad class of substrates (29 examples) were effectively transformed into the desired products in 50–97% yields under mild conditions. (Figure presented.).

Base-Promoted Sulfur-Mediated Carbonylative Cyclization of Propargylic Amines

A tBuOK-mediated carbonylative cyclization of propargylic amines with elemental sulfur has been developed. With benzene-1,3,5-triyl triformate (TFBen) as a convenient CO surrogate, various substituted 1,3-thiazolidin-2-ones were produced in good to excellent yields.

Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles

A diversity-oriented protocol giving access to a novel class of spiro-cyclic guanidine derivatives is described. The copper(I)-catalyzed, three-component coupling of a ketone, an alkyne and a primary amine (KA 2-coupling) provides the required secondary propargylamines and assures the generation of diversity. The key step of the protocol, a silver(I)-mediated tandem guanylation of secondary propargylamines followed by an intramolecular heterocyclization, provides the target bis-Boc-protected-2- iminoimidazolines spiro-fused with a five-, six- or seven-membered (heterocyclic) ring, which could, in most cases, be further deprotected to the spiro-2-aminoimidazoles. Georg Thieme Verlag Stuttgart · New York.

Unprecedented Cu(I)-catalyzed microwave-assisted three-component coupling of a ketone, an alkyne, and a primary amine

An efficient, microwave-assisted Cu(I)-catalyzed one-pot coupling of a ketone, an alkyne, and a primary amine (KA2 coupling) is described, giving access to secondary propargylamines.