File:Skraup quinoline synthesis From Wikimedia Reaction scheme of Skraup quinoline synthesis. Síntesis de quinolinas de Skraup. A practicable quinoline synthesis from aniline and two amino acids provides a .. is regiocomplementary to the traditional Skraup-Doebner-Von Miller synthesis. In the Skraup synthesis of quinoline the principal difficulty has always been the violence with which the reaction generally takes place; it occasionally proceeds.
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Skraup’s Synthesis | Vive Chemistry
Email required Address never made public. The reaction showed a broad substrate scope with very good yields. A copper-catalyzed regiocontrolled three-component reaction of nitriles, diaryliodoniums, and ynamides provides diversified 4-aminoquinolines. Views View Edit History. The utility for the scaffold decoration of a broad range of complex N -heterocycles is exemplified by syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.
H2SO4 and an oxidizing agent like nitrobenzene. Site Search any all words.
File:Skraup quinoline synthesis mechanism.svg
A copper-catalyzed tandem annulation of alkynyl skrahp with quinoilne compounds enables an efficient synthesis of a broad range of C4-functionalized quinolines in good yields via in situ formation of allene and intramolecular electrocyclization. Deuterium-labeling experiments provide direct evidence of a second equivalent of bromoaniline serving as the terminal oxidant. I, the copyright holder of this work, release this work into the public domain.
Prajapati, Synlett, The transformation is effective skrahp a broad range of substrates, including aliphatic alcohols, arylalkanols, cycloalkanols, and ethylene glycol. If the file has been modified from its original state, some details such as the timestamp may not fully reflect those of the original file. A straightforward and efficient Yb OTf 3 catalyzed three-component reaction of aldehydes, alkynes, and amines under microwave irradiation in an ionic liquid provides 2,4-disubstituted quinolines in excellent yield under mild reaction condition.
Synthesis of quinolines
A combination of both catalysts is necessary; the use of either catalyst alone does not give the product. The resulting 3-iodoquinolines can be further functionalized by various coupling reactions. DMSO acts not only as solvent but also as one carbon source.
The reductive cyclization to quinolines is achieved in the presence of iron or oc dithionite under metal-free conditions. Description Skraup quinoline synthesis mechanism. Knochel, Synlett, 26 An iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage and C-H activation utilizes inexpensive FeCl 3 as promoter and is suitable for forming various 3-arylquinolines from simple and readily available starting materials.
An eco-friendly method allows the synthesis of 2,4-disubstituted quinolines via Meyer-Schuster rearrangement of 2-aminoaryl ketones and phenylacetylenes in the presence of a catalytic amount of zinc trifluoromethanesulfonate in the ionic liquid [hmim]PF 6.
The catalyst can be recycled up to four times.
Notify me of new comments via email. An efficient and regioselective alkenylation of azaheterocycle N-oxides with alkenes is catalyzed by iodine under metal- and external oxidant-free reaction conditions to provide various E styrylazaheterocycles in good yields. Shi, Synlett, 26 Vive Chemistry My rendezvous with chemistry…. The reactions proceed with high atom efficiency via a sequence of dehydrogenation and condensation steps in very good isolated yields.
File:Skraup quinoline synthesis – Wikimedia Commons
Furthermore, this process can be synthesiss extended to synthesis of various 6 H -indolo[2,3- b ]quinolines via an intramolecular Buchwald-Hartwig cross-coupling reaction in a two-step one-pot manner. Lal, Synlett, 28 A regioselective 6- endo – trig intramolecular oxidative cyclization enabled an efficient synthesis of 2-aryl 4-substituted quinolines from stable and readily available o -cinnamylanilines with KO t Bu as a mediator and DMSO as an oxidant at rt.
Compatibility of this chemistry with various functional groups is noteworthy.