323204-69-9Relevant academic research and scientific papers
Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide
Chen, Yifeng,Turlik, Aneta,Newhouse, Timothy R.
supporting information, p. 1166 - 1169 (2016/02/18)
A practical and direct method for the α,β-dehydrogenation of amides is reported using allyl-palladium catalysis. Critical to the success of this process was the synthesis and application of a novel lithium N-cyclohexyl anilide (LiCyan). The reaction conditions tolerate a wide variety of substrates, including those with acidic heteroatom nucleophiles.
A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
Lu, Nianhong,Wang, Lihong,Li, Zhanshan,Zhang, Wei
supporting information; experimental part, p. 192 - 200 (2012/04/10)
A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by the coupling reactions of N-acyliminium ions produced from 3-hydroxyisoindol-1-ones or 5-hydroxy-1-pyrrol-2-ones with unactivated olefins in the presence of BF 3·OEt2 at room temperature. For most of the olefins,the reactions afforded the Csp3-Csp2 cross-coupling products,but for the α-methylstyrene and 1-hexene,the Csp3-Csp3 cross-coupling products were obtained.
Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds
Sortino,Garibotto,Cechinel Filho,Gupta,Enriz,Zacchino
experimental part, p. 2823 - 2834 (2011/06/21)
The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted followed by 2,3 dichloro- and 2-methyl-substituted maleimides. They all were fungicide rather than fungistatic enhancing the importance of their antifungal activity. 2,3-Dimethyl and 2,3-diphenyl-maleimides possessed marginal or null activity. The presence of a flexible connecting chain in N-phenylalkyl maleimides appears not to be essential for antifungal activity, although its length shows a correlation with the antifungal behavior, displaying maleimides with alkyl chains of n = 3 and n = 4 the best antifungal activities in most fungi. Different substituents on the benzene ring did not have a clear influence on the activity. Values of chemical potential properties as well as of energy do not sufficiently discriminate between active and inactive compounds. Nevertheless, it was found that, although log P alone is not strong enough to properly predict the antifungal activity, the comparison of its values for compounds within the same sub-type, showed an enhancement of antifungal activity along with an increment of lipophilicity. In addition, the LUMO's electronic clouds of the highly active compounds showed to be concentrated on the imido ring, indicating that their carbon atoms are potential sites for nucleophilic attack. Same results were obtained from MEPs. Most of the active compounds did not show cytotoxic activity against human cancer cell lines and no one possessed hemolytic activity, indicating that their activity is selective to pathogenic fungi and that they are not toxic at MIC concentrations.
Chemoenzymatic total synthesis and determination of the absolute configuration of (S)-nebracetam
Yamashita, Sho,Mase, Nobuyuki,Takabe, Kunihiko
scheme or table, p. 2115 - 2118 (2009/04/11)
We have developed an asymmetric total synthesis of nebracetam 3 by a chemoenzymatic strategy. Diastereoselective Michael addition of nitromethane to the chiral lactam (S)-9d (>99% ee), which was prepared by lipase-catalyzed kinetic resolution, afforded the Michael product 10d in 99% yield with 86% de. Chemical transformations of 10d including recrystallization furnished the chiral nebracetam 3 and its derivative. The absolute configuration of the chiral (-)-nebracetam was determined to be an (S)-configuration.
N-benzyl-5-hydroxy-3-pyrrolidin-2-one by hydrogen peroxide oxidation of N-benzyl-3-phenylseleno-2-pyrrolidinone
Mun, JiYoung,Smith, Michael B.
, p. 813 - 819 (2007/10/03)
Using the known peroxide oxidation of N-benzyl-3-phenylseleno-2- pyrrolidinone with 30% hydrogen peroxide at -5°C after 3.5 h, we prepared the expected N-benzyl-3-pyrrolin-2-one. However, reaction with 30% hydrogen peroxide for 12 h (-5°C→ambient) gave the unexpected product N-benzyl-5-hydroxy-3-pyrrolidin-2-one in 84% isolated yield. This procedure is a new synthetic route to N-benzyl-5-hydroxy-3-pyrrolidin-2-one. Copyright Taylor & Francis Group, LLC.
Regioselective reduction of maleimide and citraconimide derivatives: General preparation of 5-hydroxy-1,5-dihydropyrrol-2-one
Mase, Nobuyuki,Nishi, Toshiki,Hiyoshi, Masaomi,Ichihara, Kazuhiro,Bessho, Junichiro,Yoda, Hidemi,Takabe, Kunihiko
, p. 707 - 709 (2007/10/03)
NaBH4 reduction of citraconimide derivatives regioselectively afforded 5-hydroxy-4-methyl-1,5-dihydropyrrol-2-ones, whereas NaBH4-CeCl3 or DIBAL-H reduction gave 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-ones.
