96013-55-7

Upstream product

• 413188-48-4 N-[(4-methylphenyl)sulfonyl]-4-pentenamide 
• 4083-64-1 Tosyl isocyanate 
• 98-59-9 p-toluenesulfonyl chloride 
• 675-20-7 piperidin-2-one 
• 23438-61-1 1-(toluene-4-sulfonyl)piperidin-2-one 
• 293321-16-1 3-(phenylselanyl)-1-(p-toluenesulfonyl)-2-piperidone 

Downstream Products

• 1226623-50-2 3-benzyl-1-(4-methylphenyl)sulfonyl-5,6-dihydropyridin-2(1H)-one 
• 1226623-54-6 3-(2-butynyl)-1-(4-methylphenyl)sulfonyl-5,6-dihydropyridin-2(1H)-one 
• 1226623-48-8 3-allyl-1-((4-methylphenyl)sulfonyl)-5,6-dihydropyridin-2(1H)-one 
• 1226623-46-6 1-[(4-methylphenyl)sulfonyl]-3-[(2E)-3-phenyl-2-propen-1-yl]-5,6-dihydropyridin-2(1H)-one 
• 1226623-56-8 3-(2-hydroxypropyl)-1-(4-methylphenyl)sulfonyl-5,6-dihydropyridin-2(1H)-one 
• 130291-45-1 3-methyl-1-(4-methylphenyl)sulfonyl-5,6-dihydropyridin-2(1H)-one 
• 1229643-26-8 1,1'-bis[(4-methylphenyl)sulfonyl]-5,6,3',4',5',6'-hexahydro-1H,1'H-[3,4']bipyridinyl-2,2'-dione 
• 1373152-66-9 methyl 1-(4-methoxyphenyl)-7-oxo-6-tosyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate 
• 1373152-65-8 methyl 4-oxo-1-phenyl-5-tosyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-3-carboxylate 
• 1373152-42-1 methyl 7-oxo-1-phenyl-6-tosyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate 
• 317339-77-8 4-methyl-1-tosyl-5,6-dihydropyridin-2(1H)-one 

Relevant academic research and scientific papers

Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions

A copper-catalyzed desaturation method that is suitable for converting lactones, lactams, and cyclic ketones to their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium reagents and can be carried out through a simple one-step operation. The protocol uses inexpensive catalysts and reagents and exhibits excellent scalability and functional group tolerance. Notably, tert-butyl alcohol is the only stoichiometric byproduct produced, and overoxidation is not observed. The reaction mechanism has been investigated through control experiments, deuterium labeling, radical clock, electron paramagnetic resonance, high-resolution mass spectrometry, and kinetic studies. The data obtained are consistent with a reaction pathway involving reversible α-deprotonation by a Cu(II)-OtBu species followed by further oxidation of the resulting Cu enolate.

Platinum-Catalyzed Desaturation of Lactams, Ketones, and Lactones

The development of a general platinum-catalyzed desaturation of N-protected lactams, ketones, and lactones to their conjugated α,β-unsaturated counterparts is reported. The reaction operates under mildly acidic conditions at room temperature or 50 °C. It is scalable and tolerates a wide range of functional groups. The complementary reactivity to the palladium-catalyzed desaturation is demonstrated in the efficient conversion of iodide, bromide, and sulfur-containing substrates.

Dormant versus evolving aminopalladated intermediates: Toward a unified mechanistic scenario in PdII-catalyzed aminations

PdII-catalyzed alkene aminopalladation and allylic Ci￡H activation are two competing reaction sequences sharing the same reaction conditions. This study aimed at understanding the factors that bias one or the other path in the intramolecular oxidative cyclization of two types of N-tosyl amidoalkenes. The results obtained are in accord with the initial generation of a high-energy cyclic (5- or 6-membered) aminopalladated intermediate. However, this latter species can evolve only if the following specific conditions are met: the availability of distocyclic β-H elimination pathway, the presence of a strong terminal oxidant, or the availability of a carbopalladation pathway. Conversely, the cyclic alkylpalladium complex is only a latent species in equilibrium with the initial substrate and cannot evolve. Such a reactivity hurdle leaves the way open for alternative reactivities such as allylic Ci￡H activation of the olefinic substrate to generate a η3-allyl complex followed by its interception by the nitrogen nucleophile, [3,3]-sigmatropic rearrangement, or decomposition. This study proposes a unifying mechanistic picture that connects these competing mechanisms. Asleep or awake? Unsaturated N nucleophiles react through two competing pathways under PdII catalysis: Ci￡H allylic activation and aminopalladation. New data are in accord with the initial generation of a high-energy cyclic aminopalladated intermediate (API) that can either evolve along different pathways such as β-H elimination, oxidation, or carbopalladation, or lay dormant, the latter leading to alternative types of reactivity, such as allylic Ci￡H activation or [3,3]-sigmatropic rearrangement, gaining the upper hand (see scheme; Ts=p-toluenesulfonyl). Copyright

Nitrogen ylide-mediated cyclopropanation of lactams and lactones

Cyclopropanation of α,β-unsaturated δ-lactams and δ-lactones mediated by nitrogen ylides is described. The process tolerates different alkyl halides and gives efficiently bicyclo[4.1.0]heptanes in a totally stereoselective manner. On the other hand, ε-lac

Synthesis of functionalized 1-azaspirocyclic cyclopentanones using bronsted acid or N-bromosuccinimide promoted ring expansions

Azaspirocyclic ring systems are present in a variety of alkaloids. Functionalized 1-azaspirocyclopentanones (6, 7, 11, 12) can be efficiently constructed through semipinacol ring expansion reactions of 2-(1- hydroxycyclobutyl)-p-toluenesulfonylenamides (4

Diels-Alder reactions of 5,6-dihydro-2(1H)-pyridones

The Diels-Alder reaction of achiral 5,6-dihydro-2(1H)-pyridones 12a,b and enantiopure 5,6-dihydro-2(1H)-pyridones 16a,b with a variety of diversely substituted buta-1,3-dienes under thermal or catalytic conditions, to give partially reduced isoquinolones 18-33 and 35-37, is reported. (C) 2000 Elsevier Science Ltd.

Diels-Alder reactions of 5,6-Dihydro-2(1H)-pyridones. Preparation of partially reduced cis-isoqninolones and cis-3,4-disubstituted piperidines

The Diels-Alder reactions of 5,6-dihydro-2(1H)-pyridones with a variety of diversely substituted butadienes to give partially reduced isoquinolones is reported. Reductive ozonolysis of the resulting octahydroisoquinolones gave cis-3,4-disubstituted piperidines.