Passerini and Ugi Reactions Involving Kinetically Unstable Isocyanides

Quelhas, Alexandre; Gazzeh, Houda; Roisnel, Thierry; Trolez, Yann; Guillemin, Jean‐Claude

doi:10.1002/ejoc.202100787

Cited by 3 publications

(1 citation statement)

References 29 publications

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“…Kinetically unstable propargyl isocyanides were utilized in the Ugi reaction by the group of Guillemin to generate Ugi adducts containing a propargyl unit. [30] Reaction of formaldehyde, acetic acid, t ‐butyl amine and 3‐isocyanoprop‐1‐yne in methanol solvent for 24 h produced the Ugi adduct in 50 % yield (Scheme 19 ). This Ugi adduct undergoes Sonogashira coupling with iodobenzene (2 equiv.)…”

Section: Transition Metal‐catalysed Transformationsmentioning

confidence: 99%

Propargyl Amines: Versatile Building Blocks in Post‐Ugi Transformations

Bhoraniya

Modha

2023

ChemistryOpen

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The Ugi reaction, a multicomponent reaction, allows diversity‐oriented synthesis Its importance is recognized by an exponential increase in the publications utilizing the post‐Ugi transformations as a strategy to build complex molecules via simple and sustainable processes in the recent literature. A second concept, alkyne activation through metal‐, acid‐, iodine‐catalysis and base‐mediated transformations, also leads to wonderful molecules in short and efficient synthetic routes. Combination of these two approaches via application of an alkyne‐containing component in the Ugi reaction brings the benefits of both protocols into one synthetic sequence. The propargyl amines come as an obvious choice in this context as they work wonderfully as an amine component in the Ugi reaction, while post‐Ugi alkyne activation has the potential to generate biologically interesting carbo‐ and hetero‐cyclic systems. Thus, one can compare the Ugi adduct with a pupa which has inherent property of metamorphosis into biologically interesting molecules. In this review, application of propargyl amines in the Ugi reaction is discussed with a focus on post‐Ugi transformations.

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Section: Transition Metal‐catalysed Transformationsmentioning

confidence: 99%

Propargyl Amines: Versatile Building Blocks in Post‐Ugi Transformations

Bhoraniya

Modha

2023

ChemistryOpen

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Two decades of recent advances of Passerini reactions: synthetic and potential pharmaceutical applications

2022

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Synthesis, Characterization and Chemistry of Tetrakis(Propargylisocyanide) Copper(I) Complex

Quelhas

Roisnel

Guillemin

et al. 2023

Molbank

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The kinetically unstable propargylisocyanide was reacted with the tetrakis(acetonitrile) copper(I) hexafluorophosphate and the formed complex was then involved in a copper-catalyzed alkyne-azide cycloaddition reaction (CuAAC). After the decomplexation of the adduct, the isocyanide was engaged in a Ugi reaction. By such a complexation, reactions can be carried out on the CC triple bond without the constraint of the instability of the free compound or the competitive reactivity of the isocyanide group.

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Passerini and Ugi Reactions Involving Kinetically Unstable Isocyanides

Cited by 3 publications

References 29 publications

Propargyl Amines: Versatile Building Blocks in Post‐Ugi Transformations

Propargyl Amines: Versatile Building Blocks in Post‐Ugi Transformations

Two decades of recent advances of Passerini reactions: synthetic and potential pharmaceutical applications

Synthesis, Characterization and Chemistry of Tetrakis(Propargylisocyanide) Copper(I) Complex

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