33768-41-1Relevant academic research and scientific papers
Mapping Dual-Base-Enabled Nickel-Catalyzed Aryl Amidations: Application in the Synthesis of 4-Quinolones
McGuire, Ryan T.,Lundrigan, Travis,MacMillan, Joshua W. M.,Robertson, Katherine N.,Yadav, Arun A.,Stradiotto, Mark
supporting information, (2022/02/17)
The C?N cross-coupling of (hetero)aryl (pseudo)halides with NH substrates employing nickel catalysts and organic amine bases represents an emergent strategy for the sustainable synthesis of (hetero)anilines. However, unlike protocols that rely on photoredox/electrochemical/reductant methods within NiI/III cycles, the reaction steps that comprise a putative Ni0/II C?N cross-coupling cycle for a thermally promoted catalyst system using organic amine base have not been elucidated. Here we disclose an efficient new nickel-catalyzed protocol for the C?N cross-coupling of amides and 2′-(pseudo)halide-substituted acetophenones, for the first time where the (pseudo)halide is chloride or sulfonate, which makes use of the commercial bisphosphine ligand PAd2-DalPhos (L4) in combination with an organic amine base/halide scavenger, leading to 4-quinolones. Room-temperature stoichiometric experiments involving isolated Ni0, I, and II species support a Ni0/II pathway, where the combined action of DBU/NaTFA allows for room-temperature amide cross-couplings.
E-N-(2-acetyl-phenyl)-3-phenyl-acrylamide targets abrin and ricin toxicity: Hitting two toxins with one stone
Chauhan, Vinita,Dhaked, Ram Kumar,Pathak, Uma,Phatak, Pooja,Saxena, Nandita
, (2021/09/04)
The efficacy of small molecule inhibitors (SMIs) against the enzymatic activity of Shiga toxin prompted the evaluation of their efficacy on related toxins viz. ricin and abrin. Ricin, like Shiga toxin, is listed as a category B bioweapon and belongs to th
Mild, rapid and efficient metal-free synthesis of 2-aryl-4-aryloxyquinolines via direct Csp2[sbnd]O bond formation by using diaryliodonium salts
Nahide, Pradip D.,Solorio-Alvarado, César R.
supporting information, p. 279 - 284 (2017/01/03)
An efficient ligand- and transition metal-free procedure for the direct Csp2[sbnd]O bond formation for the arylation of 2-aryl-4-quinolones was developed. The synthesis of the starting quinolones was carried out under our optimized C
Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp3)-C(sp2) Bond: Synthesis of Substituted Benzoxazinones
Verma, Ajay,Kumar, Sangit
supporting information, p. 4388 - 4391 (2016/10/11)
A transition metal (TM)-free practical synthesis of biologically relevant benzoxazinones has been established via a selective oxidative decarbonylative cleavage of an unstrained C(sp3)-C(sp2) bond employing iodine, sodium bicarbonate, and tbutyl hydroperoxide in DMSO at 95 °C. Control experiments and Density Functional Theory (DFT) calculations suggest that the reaction involves a [1,5]H shift and extrusion of CO gas as the key steps. The extrusion of CO has also been established using PMA-PdCl2.
INHIBITORS OF LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE AND USES THEREOF
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Paragraph 0320; 0321, (2016/12/26)
Herein are provided, inter alia, compounds capable of modulating the level of activity of low molecular weight protein tyrosine phosphatase (LMPTP) and methods of using the same. In embodiments, the compound has a structure according to Formula (I-A).
Synthesis and cyclisation studies of (E)-2-aryl-1-methyl-3-styrylquinolin-4(1H)-ones
Rocha, Djenisa H.A.,Pinto, Diana C.G.A.,Silva, Artur M.S.
supporting information, p. 7717 - 7721 (2015/09/07)
The synthesis of (E)-2-aryl-1-methyl-3-styrylquinolin-4(1H)-ones, through the Heck reaction of 2-aryl-3-iodo-1-methyl-quinolin-4(1H)-ones with styrene is described. 2-Aryl-3-iodo-1-methyl-2-quinolin-4(1H)-ones can be obtained efficiently in a two-step tra
N-Bu4NI-catalyzed selective dual amination of sp3 C-H bonds: Oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale
Zhao, Dan,Wang, Teng,Shen, Qi,Li, Jian-Xin
supporting information, p. 4302 - 4304 (2014/04/17)
An n-Bu4NI catalyzed domino reaction that involves selective dual amination of sp3 C-H bonds has been developed. The protocol affords a facile and efficient approach to the synthesis of imidazo[1,5-c] quinazolines under mild conditions.
Copper-mediated selective C-H activation and cross-dehydrogenative C-N coupling of 2′-aminoacetophenones
Ilangovan, Andivelu,Satish, Gandhesiri
supporting information, p. 5726 - 5729 (2013/12/04)
Isatins were obtained by cross-dehydrogenative C-N annulation and dealkylative C-N annulation of 2′-N-aryl/alkylaminoacetophenones and 2′-N,N-dialkylaminoacetophenones respectively in the presence of Cu(OAc)2·H2O/NaOAc/air. However, on reaction with CuBr, 2′-N-benzylaminoacetophenones underwent selective oxidation of an α-methylene group of amine rather than the 2-acetyl group to provide corresponding benzamides exclusively. Base played an important role in selective oxidation by lowering the temperature and time.
Synthesis and evaluation of graveoline and graveolinine derivatives with potent anti-angiogenesis activities
An, Zeng-Yun,Yan, Yi-Yong,Peng, Dan,Ou, Tian-Miao,Tan, Jia-Heng,Huang, Shi-Liang,An, Lin-Kun,Gu, Lian-Quan,Huang, Zhi-Shu
experimental part, p. 3895 - 3903 (2010/09/14)
A series of graveoline and graveolinine derivatives were synthesized. The biological results showed that most of graveoline derivatives possessed higher cytotoxicity and better inhibitive effect against the adhesion and migration of human umbilical vein e
PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF COMPLEX DISEASES AND THEIR DELIVERY BY INSERTABLE MEDICAL DEVICES
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Page/Page column 61-62, (2008/06/13)
The present invention relates to polyphenol-like compounds that are useful for inhibiting VCAM-1 expression, MCP-1 expression and/or SMC proliferation in a mammal. The disclosed compounds are useful for regulating markers of inflammatory conditions, including vascular inflammation, and for treatment and prevention of inflammatory and cardiovascular diseases and related disease states.
