126378-84-5

Upstream product

• 620-08-6 4-methoxypyridine 
• 100-59-4 phenylmagnesium chloride 
• 214626-96-7 (RS)-1-benzoyl-2-phenyl-2,3-dihydro-1H-pyridin-4-one 
• 54125-02-9 danishefsky's diene 
• 100-52-7 benzaldehyde 
• 150884-50-7 benzaldehyde N-boc imine 
• 100-58-3 phenylmagnesium bromide 
• 107971-39-1 phenyl 4-oxo-2-phenyl-3,4-dihydropyridine-1(2H)-carboxylate 
• 16118-22-2 benzylidenamine 
• 100-47-0 benzonitrile 

Downstream Products

• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 126575-05-1 DL-3-(N-formylamino)-3-phenylpropionic acid 
• 471259-71-9 (RS)-3-amino-3-phenyl-propionic acid hydrochloride 
• 653579-37-4 (RS)-1-methyl-2-phenyl-2,3-dihydro-1H-pyridin-4-one 
• 1335247-90-9 1-(3-(tert-butyldimethylsilyloxy)propyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one 
• 1335247-98-7 N-(3'-((tert-butyldimethylsilyl)oxy)propyl)-2,5-diphenyl-2,3-dihydropyridin-4(1H)-one 
• 1341193-20-1 2-phenyl-5-(2-(tert-butoxycarbonyl)vinyl)-2,3-dihydropyridin-4(1H)-one 
• 1232685-93-6 N-(2-bromo-4,5-dimethoxyphenyl)-4-oxo-2-phenyl-2,3-dihydropyridine-1-carboxamide 
• 1232685-94-7 N-(2-bromo-4-chloro-5-methoxyphenyl)-4-oxo-2-phenyl-2,3-dihydropyridine-1-carboxamide 
• 1232685-96-9 (2S)-N-(2-bromo-4-chloro-5-methoxyphenyl)-4-oxo-2-phenyl-2,3-dihydropyridine-1-carboxamide 

Relevant academic research and scientific papers

AgOTf-Catalyzed Aza-Diels-Alder Reactions of Danishefsky's Diene with Imines in Water

Aza-Diels-Alder reactions of Danishefsky's diene with imines in water took place smoothly in the presence of a catalytic amount of silver triflate to afford dihydro-4-pyridones in high yields. The silver triflate-catalyzed three-component reactions starti

Synthesis of dihydropyridone scaffolds on solid support: Resin Activation/Capture Approach/REACAP Technology

Resin Activation/Capture Approach (REACAP Technology) has been used to synthesize dihydropyridone scaffolds on solid support.

One pot solid phase synthesis of 2-substituted 2,3-dihydropyridin-4(1H)- ones on Rinkamide-resin

A novel solid phase synthesis of 2-substituted 2,3-dihydropyridin-4(1H)- ones using Rinkamide-polystyrene-resin is described. The key step involves a hetero-Diels-Alder reaction of Danishefsky's diene with solid phase bound imines, which was carefully opt

Novel Series of Dihydropyridinone P2X7 Receptor Antagonists

Identification of singleton P2X7 inhibitor 1 from HTS gave a pharmacophore that eventually turned into potential clinical candidates 17 and 19. During development, a number of issues were successfully addressed, such as metabolic stability, plasma stability, GSH adduct formation, and aniline mutagenicity. Thus, careful modification of the molecule, such as conversion of the 1,4-dihydropyridinone to the 1,2-dihydropyridinone system, proper substitution at C-5″, and in some cases addition of fluorine atoms to the aniline ring allowed for the identification of a novel class of potent P2X7 inhibitors suitable for evaluating the role of P2X7 in inflammatory, immune, neurologic, or musculoskeletal disorders.

Synthesis and structure - Activity relationship studies of novel dihydropyridones as androgen receptor modulators

A library of 3-hydroxy-2,3-dihydropyridones was synthesized, and their activities as antiandrogens were tested in the human prostate cancer cell line LNCaP. Structure-activity relationship (SAR) studies resulted in the identification of a potent compound

Lewis base catalyzed aza-diels-alder type reactions between danishefsky's dienes in the presence of lewis base catalysts. An efficient method for the synthesis of substituted 2,3-dihydropyridin-4-ones

Aza-Diels-Alder type reactions of various imines with 1-methoxy-3-trimethylsilyloxy-l,3-butadiene (Danishefsky's diene) derivatives catalyzed by Lewis bases such as lithium methoxide are described. The reaction proceeds via a stepwise pathway, i.e. first by an imino-aldol reaction followed by the acid mediated annulation to afford the corresponding 2,3-dihydropyridin-4-ones in high yields. An appropriate choice of the substituents on nitrogen plays important roles both in addition of the silyl enolates and in the subsequent annulation to form the desired cycloadducts.

Synthesis of β-amino acids based on oxidative cleavage of dihydropyridone derivatives

(Chemical Equation Presented) A new method for the synthesis of β-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NaIO4 and subsequently with base gave the corresponding β-amino acids in a one-pot procedure. The reactions have been monitored by 1H NMR indicating that the β-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.

Facile synthesis of dihydropyridones from nitriles

A short and efficient procedure for the synthesis of N-unsubstituted 2-aryl-2,3-dihydro-4(1H)-pyridinones from Danishefsky's diene and triethylborylimines is described. Trialkylborylimines were prepared in situ from nitriles and trialkylborohydrides. The method is compatible only with aromatic nitriles. 6-Substituted 5,6-dihydro-4-ethoxy-2(1H)-pyridinones have been prepared analogously, albeit in low yield, from Brassard's diene.