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Directed and Metalation of Naphthalene 1,8-Diamide: Complementing SAr Reactivity for the Synthesis of Substituted Naphthalenes.
Org Lett
March 2021
Department of Chemistry, Queen's University, Kingston, ON K7L 3N6, Canada.
Mono- and dianion species of 1,8-naphthalene diamide were generated under -BuLi/TMEDA conditions and trapped with a variety of electrophiles to give 2- and 2,7- substituted products and . Using Suzuki-Miyaura cross-coupling, mono- and di-iodinated products were converted into the corresponding 2-aryl () and 2,7-diaryl () products, respectively. The amide-amide rotation barrier of was established by VT NMR, and the structure of fluorenone structure , obtained by metalation, was secured.
View Article and Find Full Text PDFRadioiodinated 9-fluorenone derivatives for imaging α7-nicotinic acetylcholine receptors.
Medchemcomm
December 2019
Key Laboratory of Radiopharmaceuticals of Ministry of Education , College of Chemistry , Beijing Normal University, Beijing 100875 , China . Email:
A series of 9-fluoren-9-one substituents were synthesized and evaluated for imaging cerebral α7-nAChRs. -iodine substituted 9-fluorenone with high binding affinity ( = 9.3 nM) and selectivity was radiolabeled with I.
View Article and Find Full Text PDFThe chalcones derived from -alkynylacetophenones and aromatic aldehydes (yne-enones) when heated under reflux with iodine in acetic acid gave a range of benzo[]fluorenone derivatives in moderate to good yields. The transformation involves the formation of a vinyl indenone intermediate through regioselective alkyne hydration and intramolecular aldol condensation followed by electrocyclic ring closure and aromatization.
View Article and Find Full Text PDFSynthesis and radiofluorination of novel fluoren-9-one based derivatives for the imaging of α7 nicotinic acetylcholine receptor with PET.
Bioorg Med Chem Lett
May 2018
Helmholtz-Zentrum Dresden-Rossendorf, Institute of Radiopharmaceutical Cancer Research, Permoserstraße 15, Leipzig 04318, Germany.
By structure-activity relationship studies on the tilorone scaffold, the 'one armed' substituted dibenzothiophenes and the fluoren-9-ones were identified as the most potential α nAChR ligands. While the suitability of dibenzothiophene derivatives as PET tracers is recognized, the potential of fluoren-9-ones is insufficiently investigated. We herein report on a series of fluoren-9-one based derivatives targeting α nAChR with compounds 8a and 8c possessing the highest affinity and selectivity.
View Article and Find Full Text PDFReactivity of a Molecular Magnesium Hydride Featuring a Terminal Magnesium-Hydrogen Bond.
Inorg Chem
December 2016
Institute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany.
The reactivity of the molecular magnesium hydride [Mg(MeTACD·AlBu)H] (1) featuring a terminal magnesium-hydrogen bond and an NNNN-type macrocyclic ligand, MeTACD ((MeTACD)H = Me[12]aneN = 1,4,7-trimethyl-1,4,7,10-tetraazacyclododecane), can be grouped into protonolysis, oxidation, hydrometalation, (insertion), and hydride abstraction. Protonolysis of 1 with weak Brønsted acids HX such as terminal acetylenes, amines, silanols, and silanes gave the corresponding derivatives [Mg(MeTACD·AlBu)X] (X = C≡CPh, 3; HN(3,5-Me-CH), 4; OSiMe, 5; OSiPh, 6; Cl, 7; Br, 8). Single-crystal X-ray diffraction of anilide 4 showed a square-pyramidal coordination geometry for magnesium.
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