153856-53-2

Upstream product

• 2555-05-7 3-methyl-2-pyrrolidinone 
• 98-59-9 p-toluenesulfonyl chloride 
• 216210-21-8 C₁₈H₁₉NO₃SSe 
• 10019-95-1 N-tosylpyrrolidinone 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 10285-80-0 N-tosyl-3-butenylamine 
• 64-17-5 ethanol 
• 67-63-0 isopropyl alcohol 
• 75-65-0 tert-butyl alcohol 
• 74-83-9 methyl bromide 
• 887235-19-0 S-(4-pentynyl) N-3-butenyl-N-[(4-methylphenyl)sulfonyl]carbamothioate 
• 108-98-5 thiophenol 

Downstream Products

• 420131-45-9 3-methyl-2-oxo-1-(p-toluenesulfonyl)pyrrolidine-3-carboxylic acid benzyl ester 
• 862422-07-9 3-benzyl-3-methyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-one 
• 862422-18-2 3-allyl-3-methyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-ol 
• 862422-26-2 N-allyl-4-methyl-N-(3-methyl-3-vinyl-hex-5-enyl)-benzenesulfonamide 
• 862422-14-8 3-benzyl-3-methyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-ol 
• 862422-16-0 3-methyl-3-pyridin-4-ylmethyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-ol 
• 862422-24-0 N-allyl-4-methyl-N-(3-methyl-3-pyridin-4-ylmethyl-pent-4-enyl)-benzenesulfonamide 
• 862422-22-8 N-allyl-N-(3-benzyl-3-methyl-pent-4-enyl)-4-methyl-benzenesulfonamide 
• 420131-50-6 3-methyl-2-oxo-1-(p-toluenesulfonyl)pyrrolidine-3-carboxylic acid 
• 420131-49-3 3-diazoacetyl-3-methyl-1-(p-toluenesulfonyl)-2-pyrrolidinone 

Relevant academic research and scientific papers

One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles

A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.

Selective C-H Olefination of Indolines (C5) and Tetrahydroquinolines (C6) by Pd/S,O-Ligand Catalysis

Herein, we report a highly selective C-H olefination of directing-group-free indolines (C5) and tetrahydroquinolines (C6) by Pd/S,O-ligand catalysis. In the presence of the S,O-ligand, a wide range of challenging indolines, tetrahydroquinolines, and olefins was efficiently olefinated under mild reaction conditions. The synthetic potential of this methodology was demonstrated by the efficient olefination of several indoline-based natural products.

Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides

Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).

Exploration of the interrupted Fischer indolization reaction

A convergent method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. The method is convergent, mild, operationally simple, broad in scope, and can be used to access enantioenriched products. In addition, our approach is amenable to the synthesis of furoindoline and pyrrolidinoindoline natural products as demonstrated by the concise formal total syntheses of physovenine and debromoflustramine B. The strategy will likely enable the synthesis of more complex targets such as the communesin alkaloids.

An interrupted fischer indolization approach toward fused indoline-containing natural products

An efficient method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. Our studies show that the approach will likely be amenable to the synthesis of complex targets, such as the communesin natural products.

Generation and cyclization of unsaturated carbamoyl radicals derived from S-4-pentynyl carbamothioates under tin-free conditions

The radical reaction of benzenethiol with S-4-pentynyl carbamothioates provides a valuable protocol for the tin-free generation of carbamoyl radicals, which arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals. This procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones, although, for the latter, it seems of lesser utility. Novel evidence is presented that. N-tosyl-substituted carbamoyl radicals display a peculiar tendency to yield the corresponding isocyanate by β-elimination of the tosyl radical.

Synthesis of a novel series of 4,4-disubstituted 2,3,4,7-tetrahydroazepines

A general, simple and straightforward strategy for the synthesis of a novel series of 4,4-disubstituted 2,3,4,7-tetrahydroazepines is described. This route involves a one-pot Wittig olefination/N-allylation process on a five-membered hemi-aminal followed by a final ring closing metathesis reaction.

Palladium-catalyzed carbonylation of homoallylic amine derivatives in the presence of a copper co-catalyst

γ-Lactams were synthesized from N-tosylhomoallylamines by a carbonylation reaction catalyzed by palladium and copper salts under the normal pressure of CO and O2 at room temperature. Monocarbonylation proceeded by the use of [PdCl2(C

Cyclization-cycloaddition cascades for the construction of azapolycyclic ring systems

Cyclic 2-amidofuranones were obtained from the Rh(II)-catalyzed reaction of α-diazoketo substituted pyrrolidine derivatives. These compounds are derived by a [1,4]-hydrogen transfer from an initially formed carbonyl ylide dipole. Acylation of the amido-substituted furanone with pivalyl chloride provided a fused amidofuran, which underwent bimolecular Diels-Alder cycloaddition with N-phenylmaleimide. The Rh(II)-catalyzed decomposition of ethyl 2-diazo-3-oxo-(2-oxo-1-pent-4-enoyl-pyrrolidine-3-yl)propionate was also examined. In this case, the alkenyl group tethered to the amido carbonyl underwent smooth intramolecular [4+2]-cycloaddition with the amidofuran obtained from the acylation reaction. An alternate route for the synthesis of cyclic amidofurans was developed using a Pummerer induced cyclization of the thiophenyl substituted acetal derived from the aldol reaction of methoxyphenylsulfanyl acetaldehyde with α-valerolactam. Treatment of the amido-substituted acetal with dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) generated an oxonium ion, which readily cyclized onto the adjacent carbonyl group. The amidofuran that was formed underwent an intramolecular Diels-Alder reaction when heated at 110°C in toluene. Subsequent ring opening of the transient [4+2]-cycloadduct followed by elimination of methanol and tautomerization of the resulting cyclohexadienone gave rise to the observed phenolic lactam in good overall yield.

Carbamoyl radicals from se-phenylselenocarbamates: Intramolecular additions to alkenes

A series of 5 exo-trig cyclizations of carbamoyl radicals generated from readily available Se-phenylselenocarbamates is reported. Kinetic studies indicate that the rate constant of this cyclization exceeds 1 x t 08s-1 in several cases.