888329-88-2

Usage

Uses

Used in Organic Synthesis:
3-(2-phenylethynyl)oxazolidin-2-one is used as a building block for the synthesis of various organic compounds due to its high reactivity and strong polarization.
Used in Asymmetric Synthesis:
3-(2-phenylethynyl)oxazolidin-2-one is used as a useful reagent in asymmetric synthesis, enabling the selective formation of enantiomerically pure compounds.
Used in the Preparation of Highly Reactive Keteniminium Ions:
3-(2-phenylethynyl)oxazolidin-2-one serves as a precursor for the generation of highly reactive keteniminium ions, which are valuable intermediates in organic chemistry for the synthesis of a wide range of target molecules.

Upstream product

• 497-25-6 dimethylenecyclourethane 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 536-74-3 phenylacetylene 
• 768-60-5 4-methoxyphenylacetylen 
• 637-44-5 phenylpropyolic acid 
• 1258403-15-4 1-((Z)-2-bromo-1-iodovinyl)benzene 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 100-52-7 benzaldehyde 
• 1483-82-5 phenylethynyl chloride 
• 58723-96-9 (Z)-1,2-dichloro-2-phenylethylene 
• 7436-90-0 2,2-dibromostyrene 
• 71-43-2 benzene 

Downstream Products

• 1039487-45-0 3-(5-phenyl-3-p-tolyl-3H-1,2,3-triazol-4-yl)oxazolidin-2-one 
• 1085526-73-3 3,3'-(2-phenylethene-1,1-diyl)dioxazolidin-2-one 
• 1134172-72-7 3-[(Z)-1-(4-nitrophenyl)-2-phenylbut-1-enyl]oxazolidin-2-one 
• 1134172-74-9 methyl (2E,4Z)-4-(2-oxooxazolidin-3-yl)-5-phenylhepta-2,4-dienoate 
• 1134172-63-6 3-[(Z)-2-phenylbuta-1,3-dienyl]oxazolidin-2-one 
• 478918-54-6 3-[(1Z)-2-phenylprop-1-en-1-yl]-1,3-oxazolidin-2-one 
• 1134172-46-5 3-[(1Z)-2-phenylbut-1-en-1-yl]-1,3-oxazolidin-2-one 
• 1134172-70-5 3-[(Z)-1-benzoyl-2-phenylbut-1-enyl]oxazolidin-2-one 
• 1187370-50-8 (E)-3-(1-(2-iodophenylimino)-2-phenylethyl)oxazolidin-2-one 
• 1187370-69-9 3-(2-phenyl-1H-indol-3-yl)oxazolidin-2-one 
• 1187370-67-7 3-(3-phenyl-1H-indol-2-yl)oxazolidin-2-one 
• 1187370-52-0 (E)-3-(1-(4-chloro-2-iodophenylimino)-2-phenylethyl)oxazolidin-2-one 
• 1187370-51-9 (E)-3-(1-(2-chlorophenylimino)-2-phenylethyl)oxazolidin-2-one 
• 1187370-60-0 (E)-ethyl 4-(1-(2-oxooxazolidin-3-yl)-2-phenylethylideneamino)benzoate 

Relevant academic research and scientific papers

A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes

We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).

Nickel-catalyzed regioselective hydroamination of ynamides with secondary amines

The first Ni(OTf)2-catalyzed hydroamination of ynamides 2 was developed by reacting with secondary amines (1 and 4). This protocol features excellent regioselectivity, a broad substrate scope of secondary aryl amines, and good functional group tolerance for ynamides. Using this method, a variety of substituted ethene-1,1- diamine compounds were prepared in moderate to excellent yields with high 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.

Yb(iii)-catalysedsyn-thioallylation of ynamides

Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.

One-pot synthesis of alkynylthiocyanates by phase-transfer reagent

Thiocyano-group widely exist in natural products and drug structures. A novel one-pot synthesis of alkynylthiocyanates from terminal alkynes, [hydroxy(tosyloxy)iodo]benzene and potassium thiocyanate by phase-transfer reagent involving the hypervalent iodine intermediates in transition metal-free conditions was developed. The internal alkynylthiocyanates could be used to synthesize some important compounds such as 5-thiocyanato-1,2,3-triazoles and (Z)-α-thiocyanato-vinyl trifluoromethanesulfonate.

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.

Room temperature palladium-catalyzed hydroarylation of ynamides in water

Pd-catalyzed hydroarylation reactions of ynamides were studied in pure water in the presence of the water-soluble industrial TPPTS ligand in comparison with the use of PCy3 or P(o-Tol)3. Pd(OAc)2/TPPTS (3,3′,3″-phosphanetriyltris(benzenesulfonic acid) trisodium salt) system exhibited high activity for the conversion of various aryl- and alkyl-ynamides in the presence of arylboronic acids bearing either electron-donating and electron-withdrawing groups. The hydroarylation reactions allowed the formation of (Z)-α,β-disubstituted enamides as major compounds in the case of arylynamides and as unique isomer in the case of alkylynamides. The reaction conditions were optimized and the presence of a base was necessary for the efficient preparation of enamides at room temperature. Conversely, α,β-disubstituted or β,β′-disubstituted enamides were isolated as major single stereoisomers and at room temperature in water in the absence of any additive by using PCy3 or P(o-Tol)3, respectively. The best activity was observed for oxazolidin-2-one, whereas other a tosylynamide was non-reactive.

Catalyst-Free [4+2] Cycloaddition of Ynamides with 2-Halomethyl Phenols to Construct 2-Amino-4 H-Chromenes and α-Halo Enamides Simultaneously

We report the development of a facile protocol for the [4+2] cycloaddition of ynamides and 2-halomethyl phenols to afford the corresponding 2-amino-4H-chromenes and α-halo enamides under catalyst-free conditions. The reaction proceeds under mild condition

Aerobic oxidative alkynylation of H-phosphonates and amides: An efficient route for the synthesis of alkynylphosphonates and ynamides using a recyclable Cu-MnO catalyst

An atom-economical and efficient route for the synthesis of alkynylphosphonates and ynamides by aerobic oxidative alkynylation of H-phosphonates and amides with both aliphatic and aromatic alkynes using our synthesized recyclable heterogeneous Cu-MnO catalyst has been developed. The phosphorylation was carried out under base- and ligand-free conditions, and in the presence of air as the sole oxidant. The reaction is compatible with a wide variety of functional groups and generates alkynylphosphonate and ynamide products in good to excellent yields. Both reactions can be scaled up to the gram scale without any decrease in the reaction yield and the reaction time is less compared to literature reports. The catalyst is recyclable and reused several times without any significant loss of reactivity.

Transition-Metal-Free One-Step Synthesis of Ynamides

A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.