39856-59-2

Upstream product

• 56203-20-4 phenyl-acetic acid acetonylamide 
• 103-80-0 phenylacetyl chloride 
• 2450-71-7 Propargylamine 
• 174271-37-5 2-phenyl-N-(prop-2-yn-1-yl)acetamide 

Relevant academic research and scientific papers

New rearrangement of oxazolium salts into Δ3-pyrrolin-2-ones

The possibility of recyclizing oxazolium salts into Δ3-pyrrolin-2-ones by the action of base has been shown for the first time. 1998 Plenum Publishing Corporation.

Zn(OTf)2-catalyzed, microwave-promoted synthesis of 2-substituted 5-methyloxazoles from propargylic amides

The versatile conversion of propargylic amides to the respective 2-substituted 5-methyloxazoles was efficiently catalyzed by Zn(OTf)2 (5 mol%) under microwave irradiation in toluene. The method was applicable to a wide range of aliphatic, aroma

Erratum to “Zn(OTf)2-catalyzed, microwave-promoted synthesis of 2-substituted 5-methyloxazoles from propargylic amides” (Tetrahedron Letters (2019) 60(11) (777–779), (S0040403919301182), (10.1016/j.tetlet.2019.02.011))

The publisher regrets that Tables 1 and 2 in the published article do not appear in the correct format. The tables have been corrected in the online article and can be seen here: The publisher would like to apologise for any inconvenience caused.

Readily switchable one-pot 5-exo-dig cyclization using a palladium catalyst

A convenient, ligand-free, Pd(OAc)2-catalyzed one-pot reaction has been developed for the synthesis of oxazolines and oxazoles from easily available acid chlorides and propargylamine. The reaction pathways could be easily modulated to selectively obtain oxazolines or oxazoles by merely changing the additives. This method proceeds via in situ sequential nucleophilic addition/elimination reactions followed by an intramolecular 5-exo-dig cycloisomerization reaction. An interesting observation in this case is the effect of an additive: a basic additive such as triethylamine resulted in the formation of 5-methylene oxazolines, while an acidic additive such as acetic acid resulted in the formation of 5-methyloxazoles. With the current protocol we are able to obtain good to moderate yields of the desired product without the need for the isolation of intermediates.

Cyclization of propargylic amides: Mild access to oxazole derivatives

The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxazoles with interesting optical properties. Furthermore, the scope of the gold(I)-catalyzed alkylidene synthesis was investigated. Further functionalizations of these isolable intermediates of the oxazole synthesis were developed and chelate ligands can be obtained. The use of Barluenga's reagent offers a new and mild access to the synthetically valuable iodoalkylideneoxazoles from propargylic amides, this reagent being superior to other sources of halogens.