13941-99-6

Upstream product

• 78607-65-5 N-benzoyl-2-aza-3-oxabicyclo(2.2.1)heptane 
• 930-30-3 cyclopent-2-enone 
• 55-21-0 benzamide 
• 65-85-0 benzoic acid 
• 108732-34-9 benzoic acid isobutoxycarbonyl ester 

Relevant academic research and scientific papers

Palladium-catalyzed hydroamidation reaction of enones

A catalytic amount of Pd(PhCN)2Cl2 promotes conjugate addition reaction of amides with enones to afford β-amidoketones (aza-Michael reaction, hydroamidation reaction) under solvent-free conditions. The produced β-amidoketones could be transformed into multi-substituted piperidinones.

Solvent-free Br?nsted acid-catalyzed Michael addition of nitrogen- and carbon-containing nucleophiles by ultrasound activation

A new method has been developed for the Michael addition of nitrogen- and carbon-containing nucleophiles to cyclic enones. Using this conjugate addition reaction, a variety of different nucleophiles can react with a range of cyclic enones in the presence

Solvent-free Br?nsted acid-catalyzed Michael addition of nitrogen- and carbon-containing nucleophiles by ultrasound activation

A new method has been developed for the Michael addition of nitrogen- and carbon-containing nucleophiles to cyclic enones. Using this conjugate addition reaction, a variety of different nucleophiles can react with a range of cyclic enones in the presence

Catalyst control over regio- and enantioselectivity in baeyer-villiger oxidations of functionalized ketones

We report a peptide-based catalyst that can strongly influence the regio- and enantioselectivity of the Baeyer-Villiger (BV) oxidation of cyclic ketones bearing amide, urea, or sulfonamide functional groups. Both types of selectivity are thought to arise from a catalyst-substrate hydrogen-bonding interaction. Furthermore, in selected cases, the reactions exhibit the hallmarks of parallel kinetic resolution. The capacity to use catalysis to select between BV products during an asymmetric process may have broad utility for both the synthesis and diversification of complex molecules, including natural products.

Catalytic conjugate additions of nitrogen-, phosphorus-, and carbon-containing nucleophiles by amphoteric vanadyl triflate

(Chemical Equation Presented) A series of carbamates, amides, N-tosyl amides, (hetero)arenes, and hydrogen phosphines/phosphites has been examined as nucleophiles for (hetero)Michael-type additions to enones and enamides catalyzed by amphoteric vanadyl triflate under mild and neutral conditions. The newly developed C-N, C-P, and C-C bond-formation protocols were carried out smoothly in good to high yields without intervention of any 1,2-additions.

NOVEL THERMOLYTIC TRANSFORMATION OF N-BENZOYL 2-AZA 3-OXA BICYCLO(2.2.1)HEPT-5-ENE AND N-BENZOYL 2-AZA 3-OXA BICYCLO(2.2.1)-HEPTANE

Novel thermolytic pathways were encountered in careful studies with N-benzoyl 2-aza 3-oxa bicyclo(2.2.1)heptene (1) and N-benzoyl 2-aza 3-oxa bicyclo(2.2.1)heptane (2).Compound 1 thermally fragments by four pathways, namely, (3,3)-sigmatropic shift, (4+2)-cycloreversion, N-O rupture and C-N homolysis.The (3,3)-sigmatropic shift provides a novel route to unusual, bicyclic heterocycles.Electron withdrawing aryl groupings tend to promote the (3,3)-sigmatropic shift pathway over others.The (4+2)-cycloreversion of 1 leads to nitroso carbonyl benzene and cyclopentadiene.The weak ? bonds of PhCONO undergo ready homolysis.The intermediate arising from N-O rupture leads to a cyclopentenone radical similar to that involved in the PG endoperoxide -> PGE change.This radical either combines with benzoyl radical leading to 4-dibenzoylamino cyclopentenone or is transformed to an enamide by loss of hydrogen.The N-O rupture leads to the formation of benzanilide.Nitrosocarbonyl benzene is a powerful electrophile.With cyclohexene it forms a hydroximic ester, initiated by nucleophile acceptance at the CO oxygen.In contrast, it reacts with P(OMe)3 leading to diphenylurea via nucleophile acceptance at N=O oxygen.Thermolysis of 2 proceeds largely by N-O rupture, similar to that normally observed in the PG endoperoxide -> PGE change.