3430-09-9Relevant academic research and scientific papers
Late-stage synthesis and application of photoreactive probes derived from direct benzoylation of heteroaromatic C-H bonds
Hesp, Kevin D.,West, Graham M.,Xiao, Jun
, p. 3669 - 3673 (2020)
A C-H functionalization strategy for the expedient access to photoreactive chemical probes of commonly found heterocyclic fragments or drug molecules of pharmaceutical relevance is described. A series of aryl glyoxylic acid reagents featuring pendant alkyne or azide clickable handles have been developed for application in the radical-mediated appendage of benzoyl fragments onto simple heteroaromatic fragments, as well as more complex drug-like compounds. This unprecedented strategy of chemical probe synthesis allows for direct access to photoreactive chemical probes without any requirement of fragment pre-functionalization or significant synthetic re-evaluation.
K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
Hunjan, Mandeep Kaur,Laha, Joydev K.
, p. 8437 - 8440 (2021/09/02)
While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.
Compound, organic electroluminescent device and electronic device
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Paragraph 0149-0151; 0152-0155, (2020/05/01)
The invention belongs to the technical field of OLEDs and provides a compound with a structure of a chemical formula 1, wherein X1, X2 and X3 are C or N, and at least one of X1, X2 and X3 is N; X4, X5and X6 are C or N, and only one N exists in X4, X5 and X6; L1 and L2 are each independently selected from the group consisting of a single bond, a C1-C20 alkylene group, a C6-C30 arylene group, a C3-C30 heteroarylene group, and a C3-C20 cycloalkylene group; Ar1 and Ar2 are each independently selected from the group consisting of a C1-C20 alkyl group, a C3-C20 cycloalkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, and Si(R1R2R3). According to the phenanthrene fused ring compound provided by the invention, compound molecules have strong planar ductility. The strong planar ductility of the compound molecules can enhance the rigidity of the material and prolong the service life of the material. Besides, the molecular parent nucleus and the aryl substituent group are prone to forming a large conjugated system, and a plurality of nitrogen atom centers exist at the same time, so that the intramolecular electron cloud density is increased, the electron mobility and the transition rate can be improved, and an organic light-emitting device has relatively high device efficiency. The invention further provides the organic light-emitting device and an electronic device.
Iron-catalyzed Minisci acylation of N-heteroarenes with α-keto acids
Wang, Xiu-Zhi,Zeng, Cheng-Chu
, p. 1425 - 1430 (2019/02/01)
An efficient and mild protocol has been developed for the Minisci acylation reactions of nitrogen-containing heteroarenes with α-keto acids. Distinct from the conventional Minisci acylation conditions, the chemistry was performed using non-noble metal Fe(II), instead of expensive Ag(I) salt, as catalyst. A wide range of substrates, including aliphatic or aromatic α-keto acids, as well as various N-heteroarenes, proved to be compatible with the protocol. Scale-up experiment also demonstrates the practicality of the approach.
Room Temperature Metal-Catalyzed Oxidative Acylation of Electron-Deficient Heteroarenes with Alkynes, Its Mechanism, and Application Studies
Sharma, Shweta,Kumar, Mukesh,Vishwakarma, Ram A.,Verma, Mahendra K.,Singh, Parvinder Pal
, p. 12420 - 12431 (2018/10/20)
Herein, we report an original one-step, simple, room-temperature, regioselective Minisci reaction for the acylation of electron-deficient heteroarenes with alkynes. The method has broad functional group compatibility and gives exclusively monoacylated products in good to excellent yields. The mechanistic pathway was analyzed based on a series of experiments confirming the involvement of a radical pathway. The 18O-labeling experiment suggested that water is a source of oxygen in the acylated product, and head space GC-MS experiment shows the C-C cleavage occurs via release as CO2.
Preparation method of acyl-substituted pyrazine compound
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Paragraph 0055, (2018/06/26)
The invention belongs to the technical field of organic synthesis and specifically discloses a preparation method of an acyl-substituted pyrazine compound. The preparation method comprises the following steps: (1) adding a silver catalyst, an oxidizing ag
Palladium-Catalyzed suzuki?Miyaura cross-Coupling of amides via site-Selective n?C bond cleavage by cooperative catalysis
Meng, Guangrong,Shi, Shicheng,Szostak, Michal
, p. 7335 - 7339 (2018/05/22)
Palladium-catalyzed Suzuki?Miyaura cross-coupling of primary benzamides enabled by a merger of site-selective N,N-di-Boc-activation and cooperative catalysis via N?C bond cleavage for the synthesis of biaryl ketones is reported. We present the synergistic combination of Lewis base and palladium catalysis as a concept to activate inert amide N?C bonds. The mild reaction conditions provide a direct route to structurally diverse ketones. The reaction tolerates a wide range of electrophilic functional groups. Considering the fundamental importance of primary amides as pharmaceutical and synthetic intermediates, the strategy has a potential for developing a diverse array of valuable amide N?C bond functionalization reactions by the synergistic merger of Lewis base and organometallic catalysis.
Convenient Stille carbonylative cross-couplings using molybdenum hexacarbonyl
Lindh, Jonas,Fardost, Ashkan,Almeida, Maria,Nilsson, Peter
experimental part, p. 2470 - 2472 (2010/07/04)
Palladium catalysis was used in Stille-type carbonylative cross-couplings employing Mo(CO)6 as the carbon monoxide source. Robust and convenient transformations were carried out in closed vessels at 100 °C, providing a set of diaryl ketones in good yields. Aryl triflates and bromides were used as coupling partners with aryl stannanes. Inclusion of the Mo(CO)6 destabilizing agent DBU made this protocol operationally simple and suppressed side-product formation.
T-CELL INHIBITING COMPOUNDS AND THEIR USE FOR THE TREATMENT OF T-CELL-MEDIATED DISEASES
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Page/Page column 27-28, (2008/12/07)
The present invention relates to compounds of formula IA or IB. The present invention also concerned to a method of treating immunologic diseases or pathological conditions in association with T cell involving an immunologic component using T-cell inhibitors, optionally in combination with one or more other drugs selected from steroids, DMARDs, NSAIDs, immunosuppressive, and biological modifiers, pharmaceutical compositions comprising said compounds of formula IA or IB together with said other drugs, and the use of T-cell inhibitors for the manufacture of a pharmaceutical composition for the treatment of immunologic diseases or pathological conditions involving an immunologic component.
Polar effects in free-radical reactions. A novel homolytic acylation of heteroaromatic bases by aerobic oxidation of aldehydes, catalysed by N-hydroxyphthalimide and Co salts
Minisci, Francesco,Recupero, Francesco,Cecchetto, Andrea,Punta, Carlo,Gambarotti, Cristian,Fontana, Francesca,Pedulli, Gian Franco
, p. 325 - 328 (2007/10/03)
A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N-oxyl radical (PINO) generated from N-hydroxyphthalimide by air oxygen and Co(II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromatic base, which is then rearomatised in a chain process. Quinazoline has an anomalous behaviour, giving 3H-quinazolin-4-one as the only reaction product.
