22411-59-2Relevant articles and documents
Aromatic amines in organic synthesis. Part ii. p‐aminocinnamaldehydes
J?drzejewska, Beata,Pietrzak, Marek
, (2021/08/03)
Ten derivatives of p‐aminocinnamic aldehydes were prepared from the reaction of either aromatic amines with dimethylaminoacrolein or benzaldehydes with acetaldehyde. Their chemical structure and purity were verified by1H NMR,13C NMR and IR spectroscopic methods. We found that the synthesis applying dimethylaminoacrolein as the reagent gets better yields than the one based on the reaction with acetaldehyde. The yields of the cinnamic aldehydes varied according to the type of the amino group and the number and position of the substituents. The basic spectroscopic properties of the p‐aminocinnamic aldehydes are also described since the compounds may be a precursor for the synthesis of dyes for diverse applications, e.g., in medicine and optoelectronics.
Synthesis of 3-[4-(dimethylamino)phenyl]alkyl-2-oxindole derivatives and their effects on neuronal cell death
Furuta, Kyoji,Kawai, Yu,Mizuno, Yosuke,Hattori, Yurika,Koyama, Hiroko,Hirata, Yoko
, p. 4457 - 4461 (2017/09/12)
Novel 3-[4-(dimethylamino)phenyl]alkyl-2-oxindole analogs were synthesized by either of the following two pathways: (1) a sequence of Knoevenagel condensation of oxindole with (4-dimethylamino)cinnamaldehyde–hydrogenation, or (2) alkylation of oxindole dianion with [(4-dimethylamino)phenyl]alkyl halides. Subsequent alkylation at C-3 and/or N-1 of the oxindole skeleton by anion-based methods provided additional substituted derivatives for structure-activity relationship studies. Their effects on neuronal cell death induced by oxidative stress were evaluated by lactate dehydrogenase assay. Compounds with the alkyl chain length of 2–4 significantly suppressed the neuronal cell death. No significant change occurred in the activity by substitution with less-polar groups. The stereochemistry at C-3 of the oxindole core was also irrelevant for the neuroprotective effects of these compounds.
Analogs of Michler's ketone for two-photon absorption initiation of polymerization in the near infrared: Synthesis and photophysical properties
Lemercier, Gilles,Martineau, Cecile,Mulatier, Jean-Christophe,Wang, Irene,Stephan, Olivier,Baldeck, Patrice,Andraud, Chantal
, p. 1606 - 1613 (2007/10/03)
We present the synthesis of substituted ketones, conjugated analogs of Michler's ketone. These molecules exhibit broadband TPA properties between 700 and 1100 nm due to a charge transfer from the terminal amino groups to the central ketone function and wi
