769-28-8Relevant articles and documents
Kinetics and Mechanism of the Condensation Reaction of Symmetrical and Unsymmetrical 1,3-Diketones with Cyanoacetamide in the Synthesis of 4,6-Disubstituted-3-cyano-2-pyridones
Misic-Vukovic, Milica,Radojkovic-Velickovic, Mirjana
, p. 1965 - 1970 (1992)
The rate constants for the condensation of cyanoacetamide with pentane-2,4-dione, 5-methylhexane-2,4-dione and 5,5-dimethylhexane-2,4-dione catalysed by piperidine were determined under a variety of experimental conditions.A UV spectrophotometric method for rate measurements was developed and the structures of the products were elucidated by means of a spectroscopic study.On the basis of the obtained rate constants, activation parameters and the evidence on the structure of synthesized unsymmetrical 4,6-disubstituted-3-cyano-2-pyridones a possible reaction scheme was suggested.It was thus possible to explain the selectivity of the reaction and the position of substituents in the pyridones obtained.
An Unusual Photodimerisation of a Pyrone Analogue; X-Ray Crystal Structure of the Principal Product
Alcock, Nathaniel W.,Samuel, Christopher J.
, p. 603 - 604 (1982)
Irradiation of 4-dicyanomethylene-2,6-dimethyl-4H-pyran (1) in methanol leads to the dimers (2) and (3); the structure of (2) has been determined by X-ray crystallography.
Synthesis, physicochemical and vibrational spectral properties of 2–pyridone and 2–aminopyridine derivatives: An experimental and theoretical study
El–Tahawy, Mohsen M. T.,Garavelli, Marco,Keshk, Reda M.
, (2020/09/01)
A convenient and efficient one–pot three–component reaction of acetyl acetone, malononitrile and ammonium acetate was investigated for the synthesis of 3–cyano–4,6–dimethyl–2–pyridone (PI) and 2–amino–3–cyano–4,6–dimethylpyridine (PII). The products were achieved with high purity, high yields and short reaction time. The yields of the two products depend on the concentration of ammonium acetate, reaction time and the solvent used. The structures of the isolated products were confirmed by elemental analysis and spectral data, supported by quantum chemical (MP2) calculations, both in gas phase and solvents (water and ethanol), that were also employed to track the reaction mechanisms and model vibrational spectral properties for final characterization and interpretation of spectral data. A remarkable matching between theoretical predictions and experiments was attained both for the geometrical parameters, as compared to X-Ray data available in the literature, and for vibrational frequencies, leading to a correlation coefficient (R2) of 0.99. Molecular docking was further studied to predict the docking binding energy of the synthesized compounds with the target proteins.
1,5,7-TRISUBSTITUTED ISOQUINOLINE DERIVATIVES, PREPARATION THEREOF, AND USE THEREOF IN MEDICINES
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Paragraph 0210-0211; 0224-0225, (2020/08/30)
The present disclosure relates to 1,5,7-trisubstituted isoquinoline derivatives, their preparation and pharmaceutical use. In particular, the present disclosure discloses a compound of formula (I) or a pharmaceutically acceptable salt, stereoisomer, solvate or prodrug thereof, and a preparation method and use thereof. The definitions of the groups in the formula can be found in the specification and claims.
5-Hydroxyindole-based EZH2 inhibitors assembled via TCCA-catalyzed condensation and Nenitzescu reactions
Chen, Guoliang,Du, Fangyu,Sun, Wenjiao,Wang, Lihui,Wu, Chunfu,Yang, Cheng,Zhou, Qifan
supporting information, (2020/05/16)
5-Hydroxyindole derivatives have various demonstrated biological activities. Herein, we used 5-hydroxyindole as a synthetic starting point for structural alterations in a combinatorial process to synthesize 22 different compounds with EZH2 inhibitor pharmacophores. A series of 5-hydroxyindole-derived compounds were screened inhibitory activities against K562 cells. According to molecular modeling and in vitro biological activity assays, the preliminary structure-activity relationship was summarized. Compound L–04 improved both the H3K27Me3 reduction and antiproliferation parameters (IC50 = 52.6 μM). These findings revealed that compound L–04 is worthy of consideration as a lead compound to design more potent EZH2 inhibitors. During the preparation of compounds, we discovered that trichloroisocyanuric acid (TCCA) is a novel catalyst which demonstrates condensation-promoting effects. To gain insight into the reaction, in situ React IR technology was used to confirm the reactivity. Different amines were condensed in high yields with β-diketones or β-ketoesters in the presence of TCCA to afford the corresponding products in a short time (10~20 min), which displayed some advantages and provided an alternative condensation strategy.
