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

Abstract

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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“…Nowadays, the most critical challenge would be the design of effective chemical reaction sequences, providing great structural complexity with minimum synthetic steps. 34,35 Multicomponent reactions (MCRs) can be regarded as transformations in which, to form the product, we need more than two starting materials. Moreover, it is worth mentioning that such reactions will nearly incorporate the atoms of the starting materials.…”

Chemical CO2 fixation using a green biocatalytic system based on Ugi conjugated cobalt phthalocyanine on cellulose

“…46 In organic chemistry, one of the most well-known classes of multicomponent reactions (MCRs) is the Ugi four-component reaction (Ugi-4CR), which contains an isocyanide, an amine, a carboxylic acid, and a ketone or aldehyde to produce a bisamide. [47][48][49] In recent years, this strategy has been established as a powerful and sustainable tool for the modication and functionalization of diverse materials. 50 The association of MCRs with materials chemistry has delivered neoteric functional structures with exible designability, developing an innovative avenue in interdisciplinary research.…”

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“…In the past decade, a wide variety of synthetic approaches have been developed to improve the sustainability of organic transformations. Among them, one-pot multicomponent reactions (MCRs) are powerful tools for the synthesis of complex heterocyclic constructions, based on procedure simplicity, energy saving, cost-effectiveness, atom economy, and green solvent compatibility [20][21][22]. Water compatibility is one notable beneficial aspect of multicomponent reaction due to being safe, eco-friendly, readily available, and inexpensive [23].…”

“…Among them, one-pot multicomponent reactions (MCRs) are powerful tools for the synthesis of complex heterocyclic constructions, based on procedure simplicity, energy saving, cost-effectiveness, atom economy, and green solvent compatibility. 20–22 Water compatibility is one notable beneficial aspect of multicomponent reactions, due to it being safe, eco-friendly, readily available, and inexpensive. 23 It is worth a mention that are still some issues regarding the reactants for water applications and organic transformation is limited.…”