Copper(I)-Catalyzed Formation of Isoquinoline and Quinoline Substituted Isobenzofurans
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Abstract:
An efficient synthetic organic transformation was developed to access isoquinoline-substituted isobenzofurans by reaction of substituted 1,5-diynes with isoquinoline N-oxides. Moderate to excellent yields of isoquinoline-derived isobenzofurans were achieved by formation of a new C–C and two C–O bonds in the presence of copper catalyst in one pot. whereas quinoline-substituted isobenzofurans were obtained when the reaction was conducted using quinoline N-oxides and 1,5-diynes in the presence copper catalyst.Keywords:
Isoquinoline
Quinoline
An efficient synthetic organic transformation was developed to access isoquinoline-substituted isobenzofurans by reaction of substituted 1,5-diynes with isoquinoline N-oxides. Moderate to excellent yields of isoquinoline-derived isobenzofurans were achieved by formation of a new C–C and two C–O bonds in the presence of copper catalyst in one pot. whereas quinoline-substituted isobenzofurans were obtained when the reaction was conducted using quinoline N-oxides and 1,5-diynes in the presence copper catalyst.
Isoquinoline
Quinoline
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Isoquinoline
Quinoline
Acetylenedicarboxylate
Dimethyl acetylenedicarboxylate
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Abstract Untersucht wird die Umsetzung von Chinolin‐ und Isochinolin‐N‐oxid mit Isoxazolderivaten zur Einführung von C‐Resten.
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Quinoline
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Abstract magnified image A one‐pot procedure for the synthesis of pyrrolo[2,1‐ a ]isoquinolines and pyrrolo[1,2‐ a ]quinolines in good to excellent yields has been reported, using quinoline or isoquinoline, phenacylbromide derivatives and activated alkynes in aqueous medium. J. Heterocyclic Chem., (2009).
Isoquinoline
Quinoline
Aqueous medium
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Studies were carried out on the hydration and hydrogenation of the triple bond in quinoline and isoquinoline derivatives containing an ethynyl substituent linked directly to the pyridine moiety. Fourteen kinds of ethynyl quinolines and isoquinolines such as 2-, 3-, 4-phenylethynylquinoline, 2-, 3-, 4-(1-hexynyl) quinoline, 2-(1-propynyl) quinoline, 1-, 3-, 4-phenylethynylisoquinoline, 1-, 3-, 4-(1-hexynyl) isoquinoline, and 1-(1-propynyl)-isoquinoline were converted into the corresponding acylmethyl derivatives with high selectivity, when they were heated in dilute sulfuric acid in the presence of mercuric sulfate. In all cases, no products due to reverse hydration were isolated. Partial catalytic reduction of the ethynyl linkage of the above compounds is possible, while exhaustive reduction afforded quinolines and isoquinolines with a saturated side chain.
Isoquinoline
Quinoline
Moiety
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Isoquinoline
Quinoline
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Abstract Die Enamine (II) reagieren mit dem N‐Oxid (I) zu den Chinolinderivaten (III), von denen (IIIb) mit verd. Salzsäure bei Raumtemperatur zum Acetamid hydrolysiert wird.
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Quinoline
Enamine
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The reaction of quinoline 1-oxide with 3-aminocrotononitrile or 3-aminocinnamonitrile in the presence of benzoyl chloride afforded 2-methyl-or 2-phenyl-imidazo [1, 2-a] quinoline-1-carbonitriles along with the 2-substituted quinoline derivatives. This reaction was also observed on isoquinoline 2-oxide and 1-methyl- and 1-phenyl-imidazo [2, 1-a] isoquinoline-2-carbonitriles were obtained. The mechanism of the reaction was described tentatively.
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Quinoline
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Abstract Chinolin‐N‐oxid (I) reagiert mit den Enaminen (III) in Gegenwart von Benzoylchlorid zu den 2‐substituierten Derivaten (IV).
Quinoline
Isoquinoline
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Abstract Bei der Hydratation der Alkinylchinoline (I) erhält man Chinolinylmethylketone (II).
Isoquinoline
Quinoline
Moiety
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