88733-56-6Relevant academic research and scientific papers
Preparation method of sulfasalazine impurity D
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Paragraph 0040; 0046; 0051; 0057, (2020/07/24)
The invention discloses a preparation method of a sulfasalazine impurity D, belongs to the field of drug impurity synthesis, and provides the preparation method of the sulfasalazine impurity D, whichis reasonable in process design, strong in operability,
Site-selective arene C-H amination via photoredox catalysis
Romero, Nathan A.,Margrey, Kaila A.,Tay, Nicholas E.,Nicewicz, David A.
, p. 1326 - 1330 (2015/10/12)
Over the past several decades, organometallic cross-coupling chemistry has developed into one of the most reliable approaches to assemble complex aromatic compounds from preoxidized starting materials. More recently, transition metal-catalyzed carbon-hydrogen activation has circumvented the need for preoxidized starting materials, but this approach is limited by a lack of practical amination protocols. Here, we present a blueprint for aromatic carbon-hydrogen functionalization via photoredox catalysis and describe the utility of this strategy for arene amination. An organic photoredox-based catalyst system, consisting of an acridinium photooxidant and a nitroxyl radical, promotes site-selective amination of a variety of simple and complex aromatics with heteroaromatic azoles of interest in pharmaceutical research. We also describe the atom-economical use of ammonia to form anilines, without the need for prefunctionalization of the aromatic component.
Transition-metal-free access to primary anilines from boronic acids and a common +NH2 equivalent
Voth, Samantha,Hollett, Joshua W.,Mccubbin, J. Adam
, p. 2545 - 2553 (2015/03/18)
Diversely substituted anilines are prepared by treatment of functionalized arylboronic acids with a common, inexpensive source of electrophilic nitrogen (H2N-OSO3H, HSA) under basic aqueous conditions. Electron-rich substrates are found to be the most reactive by this method. However, even moderately electron-poor substrates are well tolerated under the room temperature conditions. Sterically hindered substrates appear to be equally effective compared to unhindered ones. Highly electron-deficient substrates afford product in very low yields at room temperature, but moderate to good yields are obtained at refluxing temperatures. Our method is also amenable to electrophilic amination of several common boronic acid derivatives (e.g., pinacol esters). We demonstrate that it can be combined with metal-halogen exchange reactions or a variety of directed ortho metalation protocols in a "one-pot" sequence for the synthesis of aromatic amines with unique substitution patterns. DFT studies, in combination with experimental results, suggest that the reaction occurs via base-mediated activation of HSA, followed by 1,2 aryl B-N migration. This mode of activation appears to be critical for the success of the reaction and allows, for the first time, a general, electrophilic amination of boronic acids at ambient temperature.
Reversible heterochiral aggregation/dissociation of bis(2-hydroxyphenyl) diamides driven by UV/Vis irradiation
Nojiri, Akihiro,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information; experimental part, p. 2137 - 2141 (2012/04/10)
Light to dissolve: (R)- and (S)-diamides bearing a hydrogen-bonding framework (red in picture) and a trans-azobenzene unit (blue) form an insoluble heterochiral aggregate, which can be dissolved by photoisomerization of the azobenzene unit to the cis conformation by UV irradiation (365-nm). The insoluble aggregate was formed again by subsequent irradiation with visible light (>422-nm). The precipitation and dissolution is manifestly reversible. Copyright
Identification of pharmacophore model, synthesis and biological evaluation of N-phenyl-1-arylamide and N-phenylbenzenesulfonamide derivatives as BACE 1 inhibitors
Huang, Wenhai,Yu, Haiping,Sheng, Rong,Li, Jia,Hu, Yongzhou
experimental part, p. 10190 - 10197 (2009/04/07)
The pharmacophore model of arylpiperazine amide derivatives was built using Discovery Studio 2.0 software package and the best pharmacophore model (Hypo 1) was validated by Enrichment and ROC method (EF at 2%, 5% and 10% are 30.6, 12.2 and 7.7; AUC of the
ORTHO-AMINATION OF LITHIATED TERTIARY BENZAMIDES. SHORT ROUTE TO POLYSUBSTITUTED ANTHRANILAMIDES
Reed, J. N.,Snieckus, V.
, p. 3795 - 3798 (2007/10/02)
Directed lithiation of benzamides (1), phenyloxazoline (4a), methoxymethoxybenzene (4b), and O-phenyl carbamate (4c) followed by sequential treatment with TsN3 and NaBH4 constitutes a general route to synthetically useful amino aromatics 3 and 5.
