200055-89-6Relevant academic research and scientific papers
Enantioselective allene/enone photocycloadditions: The use of an inexpensive optically active 1,3-disubstituted allene
Shepard, Mary S.,Carreira, Erick M.
, p. 16253 - 16276 (1997)
We report the preparation and use of an inexpensive readily prepared optically active 1,3-disubstituted allene that may be utilized for enantioselective intramolecular allene/enone photocycloadditions. In addition, we describe novel substrates for intramo
Studies of bioactive heterocycles: Facile thio-Claisen rearrangement of propargylthio[1]benzopyran-2-ones
Majumdar,Ghosh
, p. 2115 - 2117 (2002)
Hitherto unreported 2H-thiopyrano[3,2-c][1]benzopyran-5-ones 6a-f are synthesized regioselectively in 79-85% yields by the thio-Claisen rearrangement of 4-propargylthio[1]benzopyran-2-ones 5a-f. The substrates 5a-f are synthesized by alkylation of hithert
Highly selective and sensitive coumarin–triazole-based fluorometric ‘turn-off’ sensor for detection of Pb2+ ions
Shaily,Kumar, Ajay,Parveen, Iram,Ahmed, Naseem
, p. 713 - 721 (2018)
Exposure to even very low concentrations of Pb2+ is known to cause cardiovascular, neurological, developmental, and reproductive disorders, and affects children in particular more severely. Consequently, much effort has been dedicated to the de
Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides
Fernandes, Rodney A.,Gangani, Ashvin J.,Kunkalkar, Rupesh A.
, p. 3970 - 3984 (2020/03/19)
An efficient metal-free and cost-effective method for the synthesis of coumarin and butenolide 4-sulfonates (46 examples) has been developed. The reaction involves addition of sulfonic acids to ethyl propiolates followed by lactonization, resulting in direct formation of coumarin and butenolide 4-sulfonates. This methodology has been elaborated to Sonogashira and Suzuki coupling including the synthesis of rac-tolterodine.
Synthesis, CYP 450 evaluation, and docking simulation of novel 4-aminopyridine and coumarin derivatives
Ghalehshahi, Hajar G.,Balalaie, Saeed,Sohbati, Hamid R.,Azizian, Homa,Alavijeh, Mohammad S.
, (2019/01/21)
Four series of novel compounds based on 4-aminopyridine, glatiramer acetate, pyrone, and coumarin backbones were sufficiently synthesized and identified by spectroscopic methods. CYP enzyme inhibition assays of five predominate human P450 isozymes indicate that all compounds, except for 4-hydrazide pyridine 1c, seem to be less toxic than 4-aminopyridine. Further investigation of the compounds using molecular docking experiments revealed different, the same, or stronger binding modes for most of the synthesized compounds, with both polar and hydrophobic interactions with the 1WDA and 1J95 receptors compared to benzoyl l-arginine amide and 4-aminopyridine, respectively. These results introduce the synthesized compounds as K+ channel blockers that could be considered for in vivo CNS disease studies.
Palladium-Catalyzed Synthesis of Benzothiophenes via Cross-Dehydrogenative Coupling of 4-Arylthiocoumarins and Pyrones
Zhang, Jin,Zhuang, Yuyu,Ma, Yangmin,Yang, Xiufang,Szostak, Michal
supporting information, p. 5709 - 5714 (2019/11/21)
Benzothiophenes represent a pivotal class of sulfur heterocycles and their synthesis has attracted significant attention to generate bioactive scaffolds. Herein, we report a convergent, atom- and step-economic method for the synthesis benzothiophenes by cross-dehydrogenative coupling (CDC) of 4-arylthiocoumarins in good to excellent yields. We further demonstrate cross-dehydrogenative coupling of 4-arylthio-2-pyrones to afford alternative substitution of benzothiophenes. The presence of a labile ester carbonyl moiety provides functional handle for further functionalization by coumarin deconstruction. Most crucially, the manuscript demonstrates that the use of readily accessible templated synthesis has a significant potential for the rapid assembly of sulfur heterocycles by dehydrogenative coupling mechanism.
Transition metal- and oxidant-free sulfonylation of 1-sulfonyl-1H-1,2,3-triazoles to enols for the synthesis of sulfonate derivatives
He, Xinwei,Wu, Yuhao,Zuo, Youpeng,Xie, Mengqing,Li, Ruxue,Shang, Yongjia
supporting information, p. 959 - 972 (2019/03/14)
A novel and convenient protocol for the synthesis of sulfonate derivatives via DABCO-catalyzed direct sulfonylation of 1-sulfonyl-1,2,3-triazoles to different enols has been established. This synthetic route could effectively avoid the use of transition m
Formal Carbene Insertion into C?O or C?N Bond: An Efficient Strategy for the Synthesis of 2-Substituted 2H-Chromene Derivatives from Chromene Acetals or Hemiaminal Ethers
Zhang, Dan,Hu, Wenhao
supporting information, p. 2446 - 2452 (2018/05/14)
We report the palladium/Br?nsted acid co-catalyzed formal insertion of carbene into the C?O or C?N bond of 2H-chromene acetals or hemiaminal ethers. This transformation was initiated by the Br?nsted acid-promoted cleavage of the C?O or C?N bond, followed by modification of the leaving alcohol or amino fragments with palladium carbenes, and reassembly of the modified fragments. A variety of C-2 functionalized 2H-chromene derivatives were obtained in moderate yield (43～75%) with good to excellent diastereoselectivities (up to >95:5 dr) under mild conditions. (Figure presented.).
Coumarin-4-sulfonate derivatives and preparation method thereof
-
Paragraph 0123-0125, (2021/03/03)
The invention discloses coumarin-4-sulfonate derivatives and a preparation method thereof. The structure of the coumarin-4-sulfonate derivatives is shown as formula (I) in the description, wherein R1is selected from H, C1-C5 alkyl or C1-C5 alkoxy; R2 is s
Convenient Michael addition/β-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
Padilha, Gustavo,Birmann, Paloma T.,Domingues, Micaela,Kaufman, Teodoro S.,Savegnago, Lucielli,Silveira, Claudio C.
, p. 985 - 990 (2017/02/15)
A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus.
