- Copper-Catalyzed Direct C-5 Fluorination of 8-Aminoquinolines by Remote C-H Activation
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A convenient method was developed for direct regioselective fluorination of 8-aminoquinolines at the C-5 position by copper-catalyzed remote C-H activation using Selectfluor as the electrophile fluorinating reagent. With this method, diverse fluorinated quinoline derivatives were facilely obtained under mild conditions with moderate yields.
- Luo, Si-Si,Su, Lan-Jun,Jiang, Yue,Li, Xiao-Bao,Li, Zheng-Hui,Sun, Huan,Liu, Ji-Kai
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- Synthesis of fluorine-containing 1,10-phenanthrolines using mild versions of Skraup and Doebner-von Miller reactions
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A versatile route for the synthesis of new 1,10-phenanthroline derivatives with fluorine-containing groups is described. Skraup reactions were performed with yields of 19 up to 48% and overall yields of 5 up to 13% based on different fluorinated anilines as starting materials. Ten formerly unknown derivatives were synthesized and characterized by NMR spectroscopy (1H,13C,19F), ESI mass spectrometry and elemental analysis.
- Lüdtke, Carsten,Haupt, Axel,Wozniak, Martin,Kulak, Nora
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- Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)-H bonds at room temperature
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The direct transformation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved by palladium catalysis at room temperature with good functional group tolerance. Some drugs and natural products were readily modified by this method. Merged with substitution reaction, newly formed C-X bonds can be transformed into diverse C-O, C-S, C-C and C-N bonds. A preliminary mechanism study demonstrates that solvent is crucial for C-H activation and the C-H activation step is involved in the rate-limiting step. An isolated Pd(ii) intermediate can be transformed into a halogenated product with the retention of conformation which suggests that concerted reductive elimination from Pd(iv) to form a C-X bond was favored.
- Yang, Xinglin,Sun, Yonghui,Sun, Tian-Yu,Rao, Yu
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supporting information
p. 6423 - 6426
(2016/05/24)
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- Novel Sulfonaminoquinoline Hepcidin Antagonists
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The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.
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Page/Page column 129
(2012/09/05)
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- Dual stimulatory and inhibitory effects of fluorine-substitution on mutagenicity: An extension of the enamine epoxide theory for activation of the quinoline nucleus
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Nineteen mono- and di-fluorinated derivatives of quinoline, 1,7- phenanthroline, 1,10-phenanthroline, benzo-[h]quinoline, and benzo[f]quinoline were subjected to analysis of their structure-mutagenicity relationships. For this purpose, six new fluorinated derivatives were synthesized. The results support that the enamine epoxide structure of the pyridine moiety, as well as the bay-region epoxide structure, is responsible for mutagenicity. Formation of K-region epoxides might involve a detoxification process rather than mutagenic activation.
- Saeki, Ken-Ichi,Kawai, Hiroshi,Kawazoe, Yutaka,Hakura, Atsushi
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p. 646 - 650
(2007/10/03)
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