63404-83-1

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 728, 1957 DOI: 10.1021/ja01560a062

InChI:InChI=1/C12H11NO/c1-9-7-11(8-12(14)13-9)10-5-3-2-4-6-10/h2-8H,1H3,(H,13,14)

Upstream product

• 16232-41-0 2-hydroxy-6-methyl-4-phenyl-nicotinonitrile 
• 614-16-4 Benzoylacetonitrile 
• 67-64-1 acetone 
• 3446-58-0 3-oxo-3-phenylpropanamide 
• 41220-29-5 N-carbamoylmethylpyridinium chloride 
• 1896-62-4 (E)-benzalacetone 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 100-39-0 benzyl bromide 
• 75-56-9 methyloxirane 
• 107-91-5 cyanoacetic acid amide 
• 856212-48-1 6-methyl-2-oxo-4-phenyl-2,3,4,5-tetrahydro-pyridine-3-carbonitrile 
• 23652-90-6 3-amino-1-phenylbut-2-en-1-one 
• 86119-84-8 phosphoric acid 

Downstream Products

• 127956-31-4 2-methoxy-6-phenyl-4-phenyl-pyridine 
• 72248-86-3 1,6-dimethyl-4-phenylpyridin-2(1H)-one 
• 83021-65-2 3,6-dimethyl-4-phenylpyridin-2(1H)-one 
• 1447910-65-7 dimethyl 6-methyl-2-oxo-4-phenyl-1,2-dihydropyridin-3-ylphosphonate 
• 54453-92-8 2-chloro-6-methyl-4-phenylpyridine 
• 83021-73-2 (1S,8S)-8,9-Dimethyl-11-phenyl-9-aza-tricyclo[6.2.2.0^2,7]dodeca-2,4,6,11-tetraen-10-one 
• 83021-73-2 (1R,8R)-8,9-Dimethyl-11-phenyl-9-aza-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,11-tetraen-10-one 
• 72248-88-5 dimethyl 1,2-dimethyl-3-oxo-5-phenyl-2-azabicyclo<2.2.2>octa-5,7-diene-7,8-dicarboxylate 
• 127956-38-1 1-<2-cyano-1-(4-methoxyphenyl)-ethenyl>-6-methyl4-phenyl-2(1H)-pyridinone 
• 127956-41-6 1-<2-cyano-1-(4-chlorophenyl)-ethenyl>-6-methyl-4-phenyl-2(1H)-pyridinone 
• 99934-45-9 2-Methyl-6-phenoxy-4-phenyl-pyridine 
• 83021-68-5 (1R,8R)-8-Methyl-11-phenyl-9-aza-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,11-tetraen-10-one 
• 83021-68-5 (1R,8R)-8-Methyl-11-phenyl-9-aza-tricyclo[6.2.2.0^2,7]dodeca-2,4,6,11-tetraen-10-one 

Relevant academic research and scientific papers

A novel abnormal michael reaction of 2-Acylmethyl-4,4-dimethyl-2-oxazolines with acetylenic ketones and Esters

The first example of abnormal Michael reaction of an active methylene compound, 2-acylmethyl-4,4-dimethyl-2-oxazoline with acetylenic ketone in acetonitrile is reported. The reaction accompanies 1,3-migration of the acyl group of the substrate to give 2-(3-acyl-1-buten-4-on-1-yl)-2-oxazoline, which was easily cyclized to 5-acyl-2-pyridone derivatives by treatment with silica gel. Selectivity of the reaction depends on bulkiness of all the substituents of both the substrate and the reagent. The selectivity is interpreted in terms of reduced kinetic acidity of an initial anionic adduct intermediate by both steric and electronic factors.

2-pyridone synthesis using 2-(phenylsulfinyl)acetamide

2-Pyridones were prepared by means of an efficient protocol including the 1,4-addition of 2-(phenylsulfinyl)acetamide to α,β-unsaturated ketones followed by cyclization and sulfoxide elimination.

A facile solid-phase synthesis of 3,4,6-trisubstituted-2-pyridones using sodium benzenesulfinate as a traceless linker

A facile and traceless solid-phase synthesis of 3,4,6-trisubstituted-2- pyridones has been developed using polystyrene sodium benzenesulfinate resin. The chemistry is applicable to combinatorial library synthesis.

2-Pyridones from cyanoacetamides and enecarbonyl compounds: Application to the synthesis of nothapodytine B

The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-cyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence of O2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkylcyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).