The status of isocyanide-based multi-component reactions in Iran (2010–2018)

Shaabani, Ahmad; Mohammadian, Reza; Afshari, Ronak; Hooshmand, Seyyed Emad; Nazeri, Mohammad Taghi; Javanbakht, Siamak

doi:10.1007/s11030-020-10049-7

Cited by 17 publications

(7 citation statements)

References 286 publications

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“…A fundamental solution to this type of problem is the use of multicomponent reactions (MCRs). These are convergent processes in which more than two starting materials produce a new product with high atom efficiency in a one-pot manner. , The MCRs have become a mainstay of medicinal and organic chemistry and also have found routine application in Diversity-Oriented Synthesis (DOS) to achieve a broad spectrum of compounds with reduced numbers of synthetic steps and with increased molecular complexity. − Over the past two decades, U-4CR, which involves the condensation of an aldehyde (or a ketone), an amine, a carboxylic acid and an isocyanide, has emerged as a popular strategy to meet the demands for the synthesis of multifunctional adducts, biologically active carbohydrate derivatives, and multifunctionalized polymers. − …”

Section: Introductionmentioning

confidence: 99%

Cyclic Imines in Ugi and Ugi-Type Reactions

et al. 2020

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Ugi four-component reactions (U-4CRs) are widely recognized as being highly efficient for the synthesis of pseudopeptides. However, the products of these reactions are not so interesting as drug candidates because they are not conformationally restricted enough for a potent interaction with biological targets. One possible way to overcome this problem is to replace amine and oxo components in the U-4CRs with cyclic imines in so-called Joullié−Ugi three-component reactions (JU-3CRs). This approach provides a robust single-step route to peptide moieties connected to N-heterocyclic motifs that are found as core skeletons in many natural products and pharmaceutical compounds. JU-3CRs also provide much better diastereoselectivity than their four-component analogues. We survey here the redesign of many synthetic routes for the efficient preparation of a wide variety of three-, five-, six-, and seven-membered heterocyclic compounds connected to the peptide backbone. Additionally, in the Ugi reactions based on the cyclic imines, α-acidic isocyanides, or azides can be replaced with normal isocyanides or acids, respectively, leading to the synthesis of N-heterocycles attached to oxazoles or tetrazoles, which are of great pharmaceutical significance. This Review includes all research articles related to Ugi reactions based on the cyclic imines to the year 2020 and will be useful to chemists in designing novel synthetic routes for the synthesis of individual and combinatorial libraries of natural products and drug-like compounds.

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Section: Introductionmentioning

confidence: 99%

Cyclic Imines in Ugi and Ugi-Type Reactions

et al. 2020

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“…Isocyanides, symbolically speaking, have been likened to “Jekyll and Hyde”, or a person with bipolar disorder, since they allow for highly efficient scaffold construction, which in turn facilitates hit-tolead efforts, yet they are also frequently utterly odorous to the senses. Scientists recently observed coming on board with “isocyanide phobia” owing to the strong odors; nevertheless, this quickly transforms into “isocyanide mania” once the full depth of the productivity increases and the inherent exploratory capacity of IMCRs is revealed [ 81 , 82 , 83 , 84 , 85 ]. Nowadays, isocyanides are considered as a peculiar functional organic group that undergo remarkable chemical reactions due to their exceptional reactivity for electro- and nucleophiles adding onto the isocyanide carbon [ 86 , 87 ].…”

Section: Alternative Components For Isocyanidesmentioning

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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“… Today, this one-step transformation is famous as the Passerini three-component reaction (P-3CR), known as one of the most respected reactions in organic synthesis. In organic and medicinal chemistry, the P-3CR has been generally employed . As a possible mechanism, the first step involves the protonation of aldehyde 3 by the carboxylic acid 2 to form intermediate 82 , which is then was attacked by the alkyl isocyanide 1 , and finally with carboxylate 9 nucleophilic attack and Mumm rearrangement leading to the formation of product 4 (Scheme ).…”

Section: Passerini Reactionmentioning

confidence: 99%

Sustainable Synthesis of Pseudopeptides via Isocyanide-Based Multicomponent Reactions in Water

Nazeri

Nasiriani

Farhid

et al. 2022

ACS Sustainable Chem. Eng.

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The impressive success in the synthesis of novel products via sustainable and green methods is a crucial purpose in organic synthesis. Water as a “green solvent” plays a vital role in accelerating some organic reactions, displaying unique reactivity and selectivity from conventional organic solvents. The isocyanide-based multicomponent reactions (I-MCRs) as sustainable and versatile reactions have received significant consideration in the synthesis of pseudopeptidic frames, especially in drug discovery. This is because of the unique nature of isocyanides that play as a special active reactant. I-MCRs in water as a solvent and reagent for the synthesis of pseudopeptidic compounds have become an interesting research direction, enabling simultaneous growth of both I-MCRs and green solvents toward ideal organic synthesis. The reaction rate of I-MCRs was accelerated in water as a solvent due to the lower activation volumes and condensation of several reactants into a single reactive intermediate and product. Furthermore, I-MCRs executed possibly in water are mild, easily controlled, and environmentally friendly, which conform well to “Green Chemistry” principles. On the other hand, these powerful organic syntheses in water and aqueous media are perpetuated by acceleration and reduction in the number of workups, purification, and extraction steps. The main subject of this review is I-MCRs that are performed in the water toward the sustainable synthesis of pseudopeptide structures. It deserves to be pointed out that whereas significant progress has been recently made on the MCRs in water and aqueous media for organic transformations, there is no exclusive account to focus on and publish about the eco-friendly I-MCRs for pseudopeptides. Nevertheless, we hope this themed assemblage will be attractive and useful for organic and pharmaceutical chemists and encourage more reaction development in this fascinating engaging field.

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The status of isocyanide-based multi-component reactions in Iran (2010–2018)

Cited by 17 publications

References 286 publications

Cyclic Imines in Ugi and Ugi-Type Reactions

Cyclic Imines in Ugi and Ugi-Type Reactions

Ugi Four-Component Reactions Using Alternative Reactants

Sustainable Synthesis of Pseudopeptides via Isocyanide-Based Multicomponent Reactions in Water

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