22568-12-3

Upstream product

• 17448-21-4 1-benzyl-5-hydroxy-5-methyl-pyrrolidin-2-one 
• 4124-41-8 p-toluenesulfonylanhydride 
• 13304-62-6 N-benzylacrylamide 
• 75-05-8 acetonitrile 
• 123-76-2 levulinic acid 
• 100-46-9 benzylamine 
• 55183-44-3 4-pentynoic chloride 
• 64984-60-7 4-oxo-4-[(phenylmethyl)amino]butanoic acid 
• 1271-66-5 dimethyltitanocene 
• 2142-06-5 1-(phenylmethyl)-2,5-pyrrolidinedione 
• 6089-09-4 4-pentynoic acid 
• 17416-73-8 4-oxopentanoic acid benzyl amide 
• 591-12-8 5-methyl-2-furanone 
• 112404-94-1 N-benzyl-4-pentynoic acid amide 

Downstream Products

• 23496-31-3 1,3-dihydro-5-methyl-1-(phenylmethyl)-2H-pyrrol-2-one 

Relevant academic research and scientific papers

Visible-Light-Mediated 5-exo-dig Cyclizations of Amidyl Radicals

A visible-light-mediated synthesis of 5-methylene-pyrrolidinones is reported. This constitutes to the first reported example of a 5-exo-dig hydroamination reaction involving a nitrogen-centered radical.

Highly Stable Porous-Carbon-Coated Ni Catalysts for the Reductive Amination of Levulinic Acid via an Unconventional Pathway

The catalytic conversions of biomass and its derivatives into fuels and chemicals require active and stable catalysts. Non-noble-metal catalysts typically suffer from deactivation due to the leaching and sintering of the metal species in liquid-phase reactions. In this work, we report a facile synthesis of porous-carbon-coated Ni catalysts supported on carbon nanotubes (CNFx@Ni@CNTs) by atomic layer deposition for the reductive amination of levulinic acid (LA) with amines to pyrrolidones. Under the protection of porous carbon with a moderate thickness, the optimized CNF30@Ni@CNTs catalyst showed a 99% yield of pyrrolidones and recyclability of up to 20 runs without the leaching and sintering of Ni nanoparticles. On the basis of verification experiments and density functional theory calculations, we determined that our Ni-catalyzed reductive amination of LA with amines underwent an unconventional pathway via amides as the first intermediate, followed by tandem cyclization, intramolecular dehydration, and hydrogenation to the desired pyrrolidones. This pathway was completely different from the reported imine-intermediated route in Pt-catalyzed systems. This work provides insights into the design of active and stable heterogeneous catalysts for liquid-phase reactions as well as into switching reaction pathways to realize the replacement of noble metals for the transformation of biobased multifunctional substrates.

A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides

The dienamine products formed by the reaction between polysubstituted succinimides and the Petasis reagent were subjected to isomerization under mild acidic conditions to give polysubstituted pyrroles in excellent yields (85-95%). The scope and limitations of this methodology are explored.

Cobalt-catalyzed regioselective synthesis of pyrrolidinone derivatives by reductive coupling of nitriles and acrylamides

(Chemical Equation Presented) A convenient and highly regioselective method for the synthesis of 5-methylenepyrrolidinone derivatives from various nitriles and acrylamides via a cobalt-catalyzed reductive coupling reaction is described. A possible mechani

Triflic anhydride mediated cyclization of 5-hydroxy-substituted pyrrolidinones for the preparation of α-trifluoromethylsulfonamido furans

The reaction of α-angelica lactone with alkylamines under aqueous conditions afforded 5-hydroxy-5-methylpyrrolidinones in high yield. When the reaction was carried out under anhydrous conditions, the only products obtained were the corresponding 4-oxopentanoic acid amides. Treatment of either class of compound with triflic anhydride (Tf2O) in pyridine resulted in the formation of various substituted sulfonamidofurans. The suggested mechanism involves initial formation of an iminium ion which is subsequently transformed into a transient imino triflate. Cyclization of the highly electrophilic imine onto the oxygen atom of the adjacent carbonyl group generates an imino dihydrofuran intermediate. This species reacts further with another equivalent of Tf2O to give the observed product. The nature of the Lewis acid used was found to affect the outcome of the cyclization reaction. In certain cases, the sulfonamide furan was utilized as a cycloaddition substrate for the synthesis of indolines and related heterocyclic systems.

Several convenient methods for the synthesis of 2-amido substituted furans

Several new methods for the synthesis of differently substituted 2-amidofurans are described. The thermolysis of furan-2-carbonyl azide results in a Curtius rearrangement and the resulting furanyl isocyanate was trapped with various organometallic reagents. A second method consists of a C-N cross-coupling reaction of a bromo-substituted furan with various amides, carbamates, and lactams. The CuI-catalyzed cross-coupling reaction between furanyl bromides and amides furnished 2- and 3-substituted amidofurans in 45-95% yield. The third protocol used involves the reaction of cyclic carbinol amides with triflic anhydride. The reaction proceeds under very mild conditions to provide α-(trifluoromethyl)sulfonamido-substituted furans in high yield. The resulting iminium ion derived from the reaction of the hydroxy pyrrolidinone with Tf2O undergoes a facile ring opening as a consequence of the adjacent hydroxyl group to produce an imino triflate intermediate. Subsequent cyclization of this highly electrophilic imine with the oxygen atom of the adjacent carbonyl group leads to an imino dihydrofuran that reacts further with another equivalent of Tf2O to give the observed product.

The reaction of cyclic carbinol amides with triflic anhydride as a method to prepare α-trifluoromethyl-sulfonamido furans

(Matrix presented) A novel synthesis of α -trifluoromethyl-sulfonamido furans via the reaction of cyclic carbinol amides with triflic anhydride has been developed. The reaction proceeds under very mild conditions with a wide set of representative lactams to provide the α-trifluoromethyl-sulfonamido-substituted furan in high yield. Rapid access to a 5-substituted indoline can be achieved by thermolysis of the N-but-3-enyl-substituted sulfonamido furan.

Toward the synthesis of biologically important chlorins, isobacteriochlorins, and corrins. Cyclic enamides from acetylenic amides

Cyclic enamides 1 of a type useful in the synthesis of naturally occurring chlorins, isobacteriochlorins, and corrins have been prepared by a process involving 5-exo-dig cyclization of the appropriate acetylenic amides 11. The desired cyclization is catalyzed by either n-Bu4NF or LiAl-(NHBn)4.

Synthesis of Cyclic Enamides by Intramolecular Cyclization of Acetylenic Amides.

Cyclic enamides 12 of a type useful in the synthesis of naturally occuring chlorins, isobacteriochlorins, and corrins have been prepared by a process involving Nicholas-Schreiber condensation to afford acetylenic amides 13, followed by either n-Bu4NF- or