Six‐Component Reactions and Beyond: The Nuts and Bolts

Hooshmand, Seyyed Emad; Yazdani, Hossein; Hulme, Christopher

doi:10.1002/ejoc.202200569

Cited by 10 publications

(2 citation statements)

References 186 publications

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“…Authors may offer a feasible approach involving the intermolecular trapping of nitrilium by the nitrate anion by similarity with the mechanism of the conventional Ugi reaction [ 50 ]. As indicated in Scheme 3 , the resultant nitro imidate might undergo a [ 1 , 4 ]-shift of the nitro group through a Mumm-type transfer to produce the equivalent nitramine 15 .…”

Section: Alternative Components For Carboxylic Acidsmentioning

confidence: 99%

“…The advent of multicomponent reactions (MCRs) is a promising platform for the synthesis of organic molecules, and it has been explored via the investigation of a high variety of components within a reagent class, as well as a growing number of components for the direct synthesis of a broad spectrum of chemicals [ 1 , 2 , 3 , 4 ]. MCRs, which use three or more accessible starting reactants in a single vessel, are an important class of sustainable and green synthesis, as they enhance orthodox “stop-and-go” synthesis, which requires tedious workup, isolation, and purification.…”

Section: Introductionmentioning

confidence: 99%

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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: Alternative Components For Carboxylic Acidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ugi Four-Component Reactions Using Alternative Reactants

Hooshmand

Zhang

2023

Molecules

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An Efficient Combinatorial Synthesis of Novel Thiazolidinone‐Bis Schiff Base Hybrids Using One‐Pot Multicomponent Reaction

et al. 2023

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A facile multicomponent synthesis of novel thiazolidinone-bis Schiff base hybrids has been developed using readily available starting materials. The four-component reaction of isothiocyanate, hydrazine, aldehyde and αbromoester in water readily affords thiazolidinone-bis Schiff base hybrids, whereas the five-component strategy involving the same reactants in the presence of boron trifluoride etherate in acetonitrile leads to the formation of the fully functionalized thiazolidinone-bis Schiff base hybrids.

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Catalytic Stereoselective Multicomponent Reactions for the Synthesis of Spiro Derivatives: Recent Progress

Patel

2022

Eur J Org Chem

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Spiro derivatives are important scaffolding substances found in many natural products and pharmaceuticals. In the last decade, numerous new approaches based on multicomponent reactions have been explored for the selective and efficient development of new spiro derivatives using various organocatalytic and transition metal‐based catalytic systems. This Review discusses pioneering advances in the field of catalytic stereoselective multicomponent reactions for the preparation of various spiro derivatives. These include stereoselective Michael cascade cyclization reactions, cycloadditions, diastereoselective reactions, and miscellaneous reactions for the synthesis of spiro‐hetero/carbocycles. Advances in the last decade have made it possible to synthesize various spiro compounds with good to excellent stereoselectivity under appropriate reaction conditions. However, achieving high regioselectivity in several described multicomponent reactions remains a challenge. Organocatalysts and transition‐metal‐based catalysts play a crucial role in achieving this milestone. Proposed catalytic mechanisms and supporting evidence are highlighted in this Review. The progress described in catalytic stereoselective approaches for spiro derivatives is immense. However, it is expected that new stereoselective synthetic methods will soon be developed that can be widely used for the preparation of spiro‐heterocycles/carbocycles.

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Six‐Component Reactions and Beyond: The Nuts and Bolts

Cited by 10 publications

References 186 publications

Ugi Four-Component Reactions Using Alternative Reactants

Ugi Four-Component Reactions Using Alternative Reactants

An Efficient Combinatorial Synthesis of Novel Thiazolidinone‐Bis Schiff Base Hybrids Using One‐Pot Multicomponent Reaction

Catalytic Stereoselective Multicomponent Reactions for the Synthesis of Spiro Derivatives: Recent Progress

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