Green Synthesis of Heterocycles Via<scp>MCRs</scp>

Zhang, Wei

doi:10.1002/9783527832439.ch5

Cited by 3 publications

(1 citation statement)

References 61 publications

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“…In the Ugi-4CR, an amine, an aldehyde or ketone, a carboxylic acid, and an isocyanide are used to render α-acetoamido carboxamide derivative. Ugi MCRs have been broadly implemented in the direct synthesis of a vast number of heterocyclic rings [ 12 , 13 , 14 ], asymmetric scaffolds [ 15 ], biologically active molecules [ 16 , 17 ], and facile generation of macrocycles [ 18 ] and polymers [ 19 ]. The Ugi-4CR is taken into account as a crucial step in the production of various natural products [ 20 ]; for instance, the naturally potent α-amino acid antibiotic (+)-furanomycin II was prepared to utilize the Ugi-4CR [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Ugi Four-Component Reactions Using Alternative Reactants

Hooshmand

Zhang

2023

Molecules

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The Ugi four-component reaction (Ugi-4CR) undoubtedly is the most prominent multicomponent reaction (MCRs) that has sparked organic chemists’ interest in the field. It has been widely used in the synthesis of diverse heterocycle molecules such as potential drugs, natural product analogs, pseudo peptides, macrocycles, and functional materials. The Ugi-4CRs involve the use of an amine, an aldehyde or ketone, an isocyanide, and a carboxylic acid to produce an α-acetamido carboxamide derivative, which has significantly advanced the field of isocyanide-based MCRs. The so-called intermediate nitrilium ion could be trapped by a nucleophile such as azide, N-hydroxyphthalimide, thiol, saccharin, phenol, water, and hydrogen sulfide instead of the original carboxylic acid to allow for a wide variety of Ugi-type reactions to occur.β In addition to isocyanide, there are alternative reagents for the other three components: amine, isocyanide, and aldehyde or ketone. All these alternative components render the Ugi reaction an aptly diversity-oriented synthesis of a myriad of biologically active molecules and complex scaffolds. Consequently, this review will delve deeper into alternative components used in the Ugi MCRs, particularly over the past ten years.

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Section: Introductionmentioning

confidence: 99%

Ugi Four-Component Reactions Using Alternative Reactants

Hooshmand

Zhang

2023

Molecules

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Synthesis of Azaspiro Tricyclic Scaffolds through Post‐Ugi Modifications: Scope and Limitation of Aza‐Michael Cyclization

et al. 2023

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Post-Ugi modifications offer a great tool to construct functionalized heterocycles in an atom-economic manner. Using this approach, we have constructed highly functionalized azaspiro tricyclic scaffolds that involve Ugi condensation and ipso-cyclization followed by aza-Michael ring closures. Herein, we present a detailed account of aza-Michael cyclizations with respect to substrate scope and limitations, along with new methods to prepare novel azaspiro tricyclic scaffolds.

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