One-pot conversion of phenols to anilines via Smiles rearrangement

Xie, Yongsheng; Vijaykumar, B.V.D.; Jang, Kiwan; Shin, Hong-Hyun; Zuo, Hua; Shin, Dong‐Soo

doi:10.1016/j.tetlet.2013.06.022

Cited by 20 publications

(10 citation statements)

References 34 publications

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“…Flash column chromatography (silica gel 60 N, 20:1 hexane/AcOEt) of the crude material afforded 432 mg (40% yield) of 5,7-dichloro-8-quinolinamine as a yellow solid. The spectroscopic data of 5,7-dichloro-8-quinolinamine are in good agreement with those reported in literature …”

Section: Experimental Sectionsupporting

confidence: 91%

Palladium-Catalyzed ortho-Selective C–H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions

et al. 2017

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The palladium-catalyzed ortho-selective chlorination of N-quinolinylbenzamide derivatives with hydrochloric acid was achieved under anodic oxidation conditions. The use of 5,7-dichloro-8-quinolinyl group as directing group was effective for the selective chlorination, and the reaction was applicable to benzamide derivatives bearing various functional groups. Synthesis of vismodegib was also completed using the palladium-catalyzed electrochemical C-H chlorination in two different steps.

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Section: Experimental Sectionsupporting

confidence: 91%

Palladium-Catalyzed ortho-Selective C–H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions

et al. 2017

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“…The structure of 2‐[(1‐alkyl(aryl)‐4‐cyano‐6,7‐dihydro‐5 H ‐cyclopenta[ c ]pyridin‐3‐yl)oxy]acetamides 11b , 11c , 11h , 11i , 11m , 11n and 11a , 11g , 11l (deriving from primary aliphatic amines) allowed its occurrence. In fact the presence of an alkoxyacetamide group (containing a potential nitrogen nucleophilic center, that could be further activated by sodium ethoxide, and at the same time of an oxygen atom, of ether type, potential leaving group) in a substrate strongly activated towards aromatic nucleophilic substitutions (a nitrogen pyridine atom and a cyano group are present) rendered possible Smiles rearrangements . The mechanism of this rearrangement is well known and has been recalled in our previous paper .…”

Section: Resultsmentioning

confidence: 92%

New Methods for the Synthesis of 3‐Amino‐6,7‐Dihydro‐5H‐Cyclopenta[c]Pyridine‐4‐Carbonitriles and Cyclopenta[d]Pyrazolo[3,4‐b]Pyridines via a Smiles‐type Rearrangement

Sirakanyan

Spinelli

Geronikaki

et al. 2016

Journal of Heterocyclic Chem

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“…The synthetic pathway of target compounds 8a–8e , 9a–9e , 10a–10d , 10f as shown in Scheme was started from compound 6 . 6 was treated with 48% hydrobromic acid at reflux affording 7 .…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and cytotoxic evaluation of novel furo[2,3‐b]quinoline derivatives

Wang

Shi

et al. 2018

Chem Biol Drug Des

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A number of novel furo[2,3-b]quinoline derivatives were designed and synthesized by introducing benzyl ether, benzoate, and benzenesulfonate to 6-position of furo[2,3-b]quinoline and their chemical structures were confirmed by ESI-MS, H NMR, and C NMR spectra. All target compounds were evaluated in vitro against four human cancer cell lines (HCT-116, MCF-7, U2OS, and A549) by MTT method. Cytotoxic assay showed that compounds 8a, 8e, 10a, 10b, and 10c exhibited more potent cytotoxicities compared to 2-bromine-6-hydroxy-furo-[2,3-b]quinoline (7). Compound 10c exhibited higher antiproliferative activity (IC values ranging from 4.32 to 24.96 μm) against four human cancer cell lines (HCT-116, MCF-7, U2OS, and A549) and weak cytotoxicity on normal cell HL-7702, which suggested that 10c might be an ideal anticancer candidate. Compounds 8a, 10a, 10b showed good selectivities to MCF-7 and HCT-116, which could be considered as ideal selective candidates for further study. The SARs showed that the introduction of the benzyl ether and benzenesulfonate could significantly improve cytotoxicities, while the benzoate failed to enhance potency obviously.

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One-pot conversion of phenols to anilines via Smiles rearrangement

Cited by 20 publications

References 34 publications

Palladium-Catalyzed ortho-Selective C–H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions

Palladium-Catalyzed ortho-Selective C–H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions

New Methods for the Synthesis of 3‐Amino‐6,7‐Dihydro‐5H‐Cyclopenta[c]Pyridine‐4‐Carbonitriles and Cyclopenta[d]Pyrazolo[3,4‐b]Pyridines via a Smiles‐type Rearrangement

Design, synthesis, and cytotoxic evaluation of novel furo[2,3‐b]quinoline derivatives

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