71590-96-0Relevant articles and documents
Development of Decarboxylative Cyanation Reactions for C-13/C-14 Carboxylic Acid Labeling Using an Electrophilic Cyanating Reagent
Song, Fengbin,Salter, Rhys,Chen, Lu
, p. 3530 - 3537 (2017/04/11)
Degradation-reconstruction approaches for isotope labeling synthesis have been known for their remarkable efficiency, but applications are scarce due to some fundamental limitations of the chemistries developed to date. The decarboxylative cyanation reaction, as a degradation-reconstruction approach, is especially useful in rapid carboxylic acid carbon isotope labeling, however development toward its application as a widespread technique has stalled at the early stages due to numerous limitations which include somewhat narrow applicability. Employing the electrophilic cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as the cyano source, efficient decarboxylative cyanation chemistry has been developed for aryl and alkyl carboxylic acids respectively with two rationally designed reaction pathways. The reactions provided good yields of nitrile products from carboxylic acids, with complete retention of isotopic purity from the [13CN]-NCTS used. The reaction conditions are relatively mild requiring no oxidant and no excess toxic heavy metal and the reagent [13/14CN]-NCTS is a stable, easy-to-handle crystalline solid that can be prepared quickly and effectively from the readily available [13/14C]-KCN. The following work describes this novel and efficient method for alkyl and aryl carboxylic acid isotopic labeling using a single reagent.
Synthesis and biological evaluation of 2-(3′,4′,5′-trimethoxybenzoyl)-3-N,N-dimethylamino benzo[b]furan derivatives as inhibitors of tubulin polymerization
Romagnoli, Romeo,Baraldi, Pier Giovanni,Sarkar, Taradas,Carrion, Maria Dora,Cruz-Lopez, Olga,Lopez Cara, Carlota,Tolomeo, Manlio,Grimaudo, Stefania,Di Cristina, Antonietta,Pipitone, Maria Rosaria,Balzarini, Jan,Gambari, Roberto,Ilaria, Lampronti,Saletti, Roberto,Brancale, Andrea,Hamel, Ernest
body text, p. 8419 - 8426 (2009/04/11)
Molecules that target microtubules have an important role in the treatment of cancer. A new class of inhibitors of tubulin polymerization based on the 2-(3,4,5-trimethoxybenzoyl)-2-dimethylamino-benzo[b]furan molecular skeleton was synthesized and evaluat
Sodium Bis(trimethylsily)amide and Lithium Diisopropylamide in Deprotection of Alkyl Aryl Ethers: α-Effect of Silicon
Hwu, Jih Ru,Wong, Fung Fuh,Huang, Jiann-Jyh,Tsay, Shwu-Chen
, p. 4097 - 4104 (2007/10/03)
Removal of methyl, benzyl, and methylene groups from alkyl aryl ethers is among the most popular deprotecting methods in organic synthesis. Alkali organoamides NaN(SiMe3)2 and LiN(i-Pr)2, often used as organic bases, have been developed as efficient deprotecting agents. Treatment of aryl methyl ethers with 1.5 equiv of NaN(SiMe3)2 or LiN(i-Pr)2 in THF and 1,3-dimethyl-2-imidazolidinone in a sealed tube at 185 °C produced the corresponding phenol derivatives in good to excellent yields (80-97percent). Removal of the methylene unit from benzodioxole derivatives was also accomplished by use of 2.5 equiv of these alkali organoamides. The corresponding catechols were obtained in 93-99percent yields. The activity of NaN(SiMe3)2 was proven lower than that of LiN(i-Pr)2; it is due to the steric congestion and the α-stabilizing effect of the silyl groups. Thus selective mono-O-demethylation of o-dimethoxybenzenes can be achieved by the use of NaN(SiMe3)2 but not LiN(i-Pr)2. O-Debenzylation of aryl benzyl ethers, however, can be accomplished by the use of LiN(i-Pr)2.
