Synthesis of Furoquinolines by a One‐Pot Multicomponent Cascade Reaction Catalyzed by Platinum Complexes

Barluenga, José; Mendoza, Abraham; Rodríguez, Félix; Fañanás, Francisco J.

doi:10.1002/chem.200802146

Cited by 55 publications

(11 citation statements)

References 48 publications

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“…On similar lines, Barluenga and co-workers have also reported the facile synthesis of furoquinolines 155 via hydroalkoxylation-cationic cyclization cascade from alkynol 156 and imine 157 (Scheme 62). [67] Interestingly, usage of silver salt along with platinum salt instead of HBF 4 gave a different product in comparison to the previous report (Scheme 61). More importantly, in addition to the change in the additive, the sequence of addition also played an important role.…”

Section: Transition-metal-catalyzed Intramolecular Hydroalkoxylation-cycloaddition Cascadecontrasting

confidence: 55%

Transition Metal‐Catalyzed Hydroalkoxylation of Alkynes: An Overview

Nanda

Mallik

2021

Chemistry A European J

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Oxygen-bearing motifs, mainly the congener heterocycles are ubiquitous due to their presence in various natural products and bioactive scaffolds. Although in literature, several strategies have been developed for their synthesis, hydroalkoxylation of alkynes has come forward as a method of choice and has been used extensively. In particular, hydroalkoxylation of alkynes has gained enormous attention from the synthetic community due to the rapid access to a very useful and reactive synthetic intermediate like 'enol ether'. Furthermore, to manifold the utility of these methods, reports have been developed elaborating the generation of 'enol ether' using hydroalkoxylation and their usage in various reactions in cascade or tandem manner. This review focuses on recent development on the hydroalkoxylation of alkynes for the synthesis of oxygen-containing entities.

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Section: Transition-metal-catalyzed Intramolecular Hydroalkoxylation-cycloaddition Cascadecontrasting

confidence: 55%

Transition Metal‐Catalyzed Hydroalkoxylation of Alkynes: An Overview

Nanda

Mallik

2021

Chemistry A European J

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“…Previously, t BuOK catalyzed cycloisomerization for the synthesis of endo cyclized product was established through an ionic mechanism [9] . Barleunga [10] and Belmont [11] reported the synthesis of furoquinolines using Pt and silver catalysts respectively. Later, in 2011 Hendrickson reagent‐assisted synthesis of furoquinolines through annulation reaction was discussed by the Yao group [12] …”

Section: Figurementioning

confidence: 99%

Radical Promoted Synthesis of Furoquinolines via Anomalous Dakin‐Type Reaction

et al. 2021

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A radical promoted approach for the selective synthesis of furo[3,2‐b]quinolines and benzylidene‐1,3‐dihydrofuro[3,4‐b]quinolines have been achieved from 2‐alkynyl quinoline‐3‐carbaldehydes by fine‐tuning of base and oxidant in good yields. In the presence of an oxidant, the reaction afforded the 5‐endo‐dig cyclized furoquinolines by decarbonylative intramolecular cyclization via a Dakin‐type reaction; however, in the absence of oxidant, 5‐exo‐dig cyclized products were obtained selectively through reductive intramolecular cyclization. The formation of furoquinolines was further supported by X‐ray crystallographic studies. The proposed mechanism was well supported by the control experiments.

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“…However, when the same reaction was performed with 5 mol% of PtCl 2 (cod) and 10 mol% of silver(I) hexafluoroantimonate, the reaction led to the formation of furo[3,2-c]quinoline derivative 37a in high yield and as a single diastereomer. 22 The formation of compound 37a suggests the coupling of three components -a unit of alkynol 32a and two units of imine 36a -in a process in which a molecule of 4-methoxyaniline is also delivered. The mechanism of this reaction is believed to involve the addition of the initially formed exocyclic enol ether 38 to the imine through a Mannich-type process to give amine derivative 39.…”

Section: Scheme 16mentioning

confidence: 99%

Constructing Molecular Complexity from Alkynol Derivatives: A Journey from Fischer Carbene Complexes to Tandem Catalysis with Gold and other Carbophilic Lewis Acids

Rodríguez

Fañanás

2013

Synlett

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One of the main challenges that organic chemists face is the development of new ways to obtain novel compounds in a fast, clean, and efficient manner. Among the strategies developed to achieve this goal are multicomponent and tandem reactions, which offer the opportunity of building up complex molecules from simple starting materials in a single synthetic operation. Alkynol derivatives are one example of these simple starting materials which, combined with other appropriate reagents, are easily transformed into interesting final products.The explosion of research that has occurred in recent years in the field of gold catalysis has served to further raise the value of alkynol derivatives as useful materials for multicomponent and cascade reactions. This account describes our recent work in this area and shows how simple reagents can be catalytically converted into complex molecules containing interesting motifs, such as eight-membered rings, [3.3.1]-and [3.2.1]-bicyclic compounds, quinolines, and spiroacetals. In addition, the application of the methods developed is shown in the total syntheses of some natural products, such as berkelic acid.

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Synthesis of Furoquinolines by a One‐Pot Multicomponent Cascade Reaction Catalyzed by Platinum Complexes

Abstract: Functionalized furoquinoline derivatives are easily obtained in a one‐pot three‐component coupling process that involves the reaction of 4‐pentyn‐1‐ol derivatives and N‐arylaldimines in the presence of catalytic amounts of a platinum(II) complex (see scheme).

Cited by 55 publications

References 48 publications

Transition Metal‐Catalyzed Hydroalkoxylation of Alkynes: An Overview

Transition Metal‐Catalyzed Hydroalkoxylation of Alkynes: An Overview

Radical Promoted Synthesis of Furoquinolines via Anomalous Dakin‐Type Reaction

Constructing Molecular Complexity from Alkynol Derivatives: A Journey from Fischer Carbene Complexes to Tandem Catalysis with Gold and other Carbophilic Lewis Acids

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