332183-33-2

Upstream product

• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 1258403-15-4 1-((Z)-2-bromo-1-iodovinyl)benzene 
• 637-44-5 phenylpropyolic acid 

Downstream Products

• 1092383-15-7 (R)-1-(4-benzyl-2-oxooxazolidin-3-yl)-2-phenylethane-1,2-dione 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 

Relevant academic research and scientific papers

TMSOTf-mediated approach to 1,3-oxazin-2-one skeleton through one-pot successive reduction-[4 + 2] cyclization process of imides with ynamides

A one-pot approach to access functionalized 1,3-oxazin-2-one skeleton has been developed through successive reduction and subsequent [4 + 2] cyclization process of N-Boc lactams with ynamides by TMSOTf. As a result, a number of five to seven membered ring fused bicyclic [1,2-c][1,3]oxazin-1-ones 12a-m and tricyclic derivatives 13a-f were obtained in moderate to excellent yields with excellent regioselectivities. Moreover, linear N-Boc amides 9a-e were also amenable to this transformation, and the desired 3,4-dihydro-1,3-oxazin-2-ones 14a-m were readily achieved in moderate yields with excellent regioselectivities.

Synthesis of dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline through Cu(OTf)2-catalyzed reactions of N-acyliminium ions with ynamides

An efficient approach to access functionalized dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline skeletons has been developed through the addition-cyclization process of ynamides 8 with N-acyliminium ions generated from N,O-acetals 6,7. The reactions were conducted under the catalysis of Cu(OTf)2, and a number of functionalized dihydro-[1,3]oxazino[4,3-a] isoindoles 9a-9y and tetrahydroisoquinolines 10a-10g, 11a-11p were generated in 48–98% yields. When chiral ynamides 8n-8u were used, optically pure products 11a-11p could be obtained with good to excellent yields and diastereoselectivities.

Stereoselective Synthesis of Pyrido- and Pyrrolo[1,2-c][1,3]oxazin-1-ones via a Nucleophilic Addition-Cyclization Process of N,O-Acetal with Ynamides

An efficient asymmetric approach to access functionalized pyrido- and pyrrolo[1,2-c][1,3]oxazin-1-ones has been developed through a nucleophilic addition-cyclization process of N,O-acetal with ynamides. A number of substituted ynamides 8a-8o and 3-silyloxypyrrolidine or piperidine N,O-acetals 6a, 7 were amenable to this transformation, and the desired products 9a-9o, 10a-10m were obtained with excellent regioselectivities and outstanding diastereoselectivities. Moreover, chiral ynamides 14a-14f could also experience this addition-cyclization process to afford products 15a-15f in excellent yields.

Transition-metal-catalyzed synthesis of 1,3-diynes and ynamides from 2-bromo-1-iodoalkenes

Diynes and ynamides are important products in chemical synthesis. An efficient palladium-catalyzed homocoupling reaction of 2-bromo-1-iodoalkenes to give 1,3-diynes has been developed. The reactions are conducted under convenient conditions and provide pr

Cu-catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling

Figure presented A Cu-catalyzed aerobic oxidative amidation of propiolic acids via decarboxylation under air has been developed. Only carbon dioxide is produced as byproduct in this approach. The use of air as oxidant makes this method more useful and easy to handle.

Iron-catalyzed amidation of alkynyl bromides: A facile route for the preparation of ynamides

(Chemical Equation Presented) A facile route to obtain ynamides in high yields was described. The products were achieved through the iron-catalyzed C-N coupling reaction of amides with alkynyl bromides in the presence of 20 mol % of N,N′-dimethylethane-1,2-diamine (DMEDA).

Copper-Mediated N-Alkynylation of Carbamates, Ureas, and Sulfonamides. A General Method for the Synthesis of Ynamides

(Matrix Presented) A general amination strategy for the N-alkynylation of carbamates, sulfonamides, and chiral oxazolidinones and imidazolidinones is described. A variety of substituted ynamides are available by deprotonation of amides with KHMDS followed by reaction with CuI and an alkynyl bromide.

Efficient preparations of novel ynamides and allenamides

Practical syntheses of a series of novel ynamides and allenamides are described here. While a base-induced isomerization protocol of propargyl amides leads to an array of chiral and achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.