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Upstream product

• 33440-88-9 silver phenylacetylide 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 536-74-3 phenylacetylene 
• 201024-81-9 C,N-diphenylnitrone 
• 1374324-65-8 C₂₂H₁₈N₂O 
• 93-98-1 N-phenyl benzoyl amide 

Relevant academic research and scientific papers

Metal-free synthesis of quinolines by direct condensation of amides with alkynes: revelation of N-aryl nitrilium intermediates by 2D NMR techniques

Employing triflic anhydride/2-fluoropyridine as an activation system, the coupling reactions of secondary N-aryl amides with terminal alkynes yielded substituted quinolines in moderate to excellent yields. The reaction tolerated both electron-donating and electron-withdrawing groups at the benzamide moiety. Electron-rich aryl acetylenes served as excellent coupling partners, and aliphatic terminal alkynes such as cyclopropyl and conjugate vinyl acetylenes could also be used as reaction partners. By means of 2D NMR techniques (heteronuclear multiple bond correlation (HMBC), heteronuclear single quantum correlation (HSQC)), nitrilium ions were probed as reactive intermediates which are in contrast with that suggested by Movassaghi on the basis of in situ IR monitoring experiments. On the basis of these results, a plausible mechanism for the formation of quinolines was suggested.

Microwave-assisted cerium(III)-promoted cyclization of propargyl amides to polysubstituted oxazole derivatives

Functionalized polysubstituted oxazoles are an important class of five-membered N,O-heterocycles that occur widely in the structure of natural products and fine chemicals. They are also often used as building blocks in the synthesis ofheterocyclic molecules with more complex structures. Therefore, efficient synthetic protocols based on Lewis acid promoted reactions are desirable. In this context, we report that, under microwave irradiation, the CeCl3·7H2O/NaI/I2 system is capable of promoting a 5-exo-dig cyclization of propargyl amides with good functional group tolerance. The microwave reactor also provides a more convenient and safer method for heating the reaction. This methodology represents a straightforward CeCl3·7H2O/NaI/I2 promoted cyclization using microwave irradiation to accomplish the synthesis of polysubstituted oxazole derivatives. After a wide-ranging scientific investigation on the use of cerium(III) salts as promoters for useful organic transformations, we describe here a new, microwave-assisted reaction involving the combinationof CeCl 3·7H2O/NaI/I2 for the construction of N,O-heterocycles. The study concerns the preparation of highly substituted oxazoles starting from N-propargyl carboxamides. Copyright

Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives

Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza-1-buten-3-ynes in good yields.In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products.The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used.Asymmetric induction is also observed in the reaction of phenylacetylene with α,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.

Copper-catalysed Reaction of Arylacetylenes with C,N-Diarylnitrones

Reaction of arylacetylenes with C,N-diarylnitrones is effectively catalysed by copper(I) iodide-dppe in the presence of potassium carbonate to give the corresponding 1-azabut-1-en-3-yne (iminopropyne) derivatives in good yield.

A convenient palladium-catalyzed synthesis of alkynyl substituted Schiff's bases by coupling of imidoyl chlorides with 1-alkynes

Alkyne substituted Schiff's bases 3 for example N-(1-phenyl-2-hexynylidene)aniline (3e), were conveniently synthesized from imidoyl chlorides 1 and 1-alkynes 2 in the presence of a palladium catalyst.