337974-76-2

Upstream product

• 100-52-7 benzaldehyde 
• 924-44-7 glyoxylic acid ethyl ester 
• 181768-24-1 (2-oxo-4-phenyl-but-3-enyl)-phosphonic acid dimethyl ester 
• 64-17-5 ethanol 
• 122077-91-2 C₁₂H₁₀O₃ 

Downstream Products

• 448957-97-9 (E)-3-[1-Benzyl-4-oxo-3,3-diphenyl-2-((E)-styryl)-azetidin-2-yl]-acrylic acid ethyl ester 
• 448957-99-1 (E)-3-(1-Benzyl-6-oxo-4,5,5-triphenyl-1,4,5,6-tetrahydro-pyridin-2-yl)-acrylic acid ethyl ester 

Relevant academic research and scientific papers

A novel and efficient stereo-controlled synthesis of hexahydroquinolinones via the diene-transmissive hetero-Diels-Alder reaction of cross-conjugated azatrienes with ketenes and electrophilic dienophiles

The diene-transmissive hetero-Diels-Alder (DTHDA) reactions of cross-conjugated azatrienes (divinylimines or penta-1,4-dien-3-imines) having an N-aryl, N-alkyl, or N-dimethylamino substituent have been examined. The initial reaction of the azatrienes with diphenylketene at room temperature yielded β-lactams of [2+2] cycloadducts, which upon heating underwent [1,3]-sigmatropic rearrangement to produce the formal [4+2] cycloadducts. The reaction of N-phenylazatriene with dimethylketene or dichloroketene produced the [2+2] cycloadducts only, while the reaction of N-(dimethylamino)azatriene with dichloroketene gave the [4+2] cycloadduct without heating. When the [2+2] cycloadduct has two different vinyl substituents at C-4 of the β-lactam ring, the regioselectivity of the rearrangement depends on steric factors and the electronic demand of the substituents. The second Diels-Alder reaction of the initial [4+2] cycloadducts with electron-deficient dienophiles (TCNE, N-phenylmaleimide) stereoselectively yielded hexahydroquinolinone derivatives. Similarly, a tandem intermolecular-intramolecular mode of the aza-DTHDA reactions produced tetracyclic nitrogen-containing heterocycles in a regio- and stereoselective manner.

DICARBONYL DERIVATIVES AND METHODS OF USE

Derivatives of dicarbonyl compounds having antitumor and antibiotic activity which can be used as anticancer agents.

4-[(4'-Methylphenyl)sulfonyl]-1-(trophenylphosphoranylidene)-2-butanone as a New Four-Carbon Synthon for Substituted Divinyl Ketones

The title compound and the corresponding anion have been conveniently used as precursors of substituted divinylketones in both carbo- and heterocyclization reactions in one-pot, three-step sequences leading to a wide variety of substituted carbo- and heterocyclic ring systems, as well as to multifunctionalized linear carbon frameworks. The compounds generated through the use of this multi-coupling reagent represent useful synthons for the construction of natural compounds including (+/-)-epibatidine, (-)-anabasine and (+/-)-pyrenophorin.