35487-96-8

Upstream product

• 1240530-50-0 tert-butyl 3-oxopent-4-ynyl(phenyl)carbamate 
• 19125-34-9 1-phenylpiperidin-4-one 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 140200-76-6 α,α'-dibromopentan-3-one 
• 62-53-3 aniline 

Downstream Products

• 1403769-84-5 5-(4-methoxyphenyl)-1-phenyl-2,3-dihydropyridin-4(1H)-one 
• 1572373-71-7 6-(4-methoxyphenyl)-1-phenyl-2,3-dihydropyridin-4(1H)-one 
• 1341193-17-6 (E)-5-[2-(tert-butoxycarbonyl)vinyl]-1-phenyl-2,3-dihydropyridin-4(1H)-one 

Relevant academic research and scientific papers

Dual C(sp3)?H Bond Functionalization of N-Heterocycles through Sequential Visible-Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions

Herein we describe a mild method for the dual C(sp3)?H bond functionalization of saturated nitrogen-containing heterocycles through a sequential visible-light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well-established use of iminium ion and α-amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp3)?H bonds.

Synthesis of 2,3-Dihydro-4-pyridones, 4-Quinolones, and 2,3-Dihydro-4-azocinones by Visible-Light Photocatalytic Aerobic Dehydrogenation

The synthesis of 2,3-dihydro-4-pyridones and 4-quinolones was realized by visible-light mediated photoredox-catalyzed aerobic dehydrogenation of 4-piperidones and 2,3-dihydro-4-quinolones. This method enables the synthesis of cyclic enaminones in up to 89

Synthesis of 6- and 7-membered cyclic enaminones: Scope and mechanism

Six- and seven-membered cyclic enaminones can be prepared using common, environmentally benign reagents. Amino acids are used as synthetic precursors allowing diversification and the incorporation of chirality. The key reaction in this multistep process involves deprotection of Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A β-amino elimination side reaction was identified in a few labile substrates that led to either loss of stereochemical purity or degradation. This process can be mitigated in specific cases using mild deprotection conditions. NMR and deuterium-labeling experiments provided valuable insight into the workings and limitations of this reaction. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond-making and bond-breaking, thus changing the mode of addition to a 6-endo-trig cyclization. This method can be used to construct an array of monocyclic and bicyclic scaffolds, many of which are found in well-known natural products (e.g., indolizidine, quinolizidine, and Stemona alkaloids).