A mild and efficient synthesis of monofluorinated α-lactam pseudopeptides via a novel dehydrofluorination of Ugi products

Liu, Nianjin; Cao, Song; Shen, Li; Yu, Jinlong; Zhang, Jian; Li, Hui; Qian, Xuhong

doi:10.1007/s11030-009-9209-x

Cited by 8 publications

(2 citation statements)

References 29 publications

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“…Numerous variants and post-condensation modifications of the original U-4CR have emerged [14–18]. One of them is an Ugi five-center four-component reaction (U-5C-4CR, Scheme 1), which differs from the parent U-4CR not only in the number of reacting functional groups, but also in its mechanism.…”

Section: Introductionmentioning

confidence: 99%

Expanding the substrate scope of ugi five-center, four-component reaction U-5C-4CR): ketones as coupling partners for secondary amino acids

et al. 2013

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Various symmetrical and unsymmetrical ketones were successfully coupled with secondary amino acids in the course of Ugi five-center, four-component reaction (U-5C-4CR), thus expanding the molecular diversity possible to be achieved by the reaction. The chemical yields depended on the degree of hindrance of the components employed and were satisfactory in view of possible steric interactions in the U-5C-4CR zwitterionic intermediate. The sense of diastereoinduction for reactions employing unsymmetrical ketones was examined by converting the resulting Ugi adducts into the corresponding rigid 2,6-diketopiperazine derivatives.Electronic supplementary materialThe online version of this article (doi:10.1007/s11030-013-9488-0) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Expanding the substrate scope of ugi five-center, four-component reaction U-5C-4CR): ketones as coupling partners for secondary amino acids

et al. 2013

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“…Traditionally -lactams are prepared by cyclization of -haloamides mediated by a strong base, 21 however, unwanted side reactions resulting from the use of a strong base are always a concern. In this context, Qian and co-workers reported 22 the base-free synthesis of monofluorinated -lactams 21 and 22 via a one-pot IMCR followed by an intramolecular cyclization strategy (Scheme 1). A small series of -lactam products 22 was prepared in moderate to good yields of 45-67% via the Ugi-4CR between gem-difluoromethylene isocyanide 20 with aldehydes, amines, and acids followed by dehydrofluorination under solvent-free heating conditions.…”

Section: Developments In Lactam Synthesis 21 -Lactamsmentioning

confidence: 99%

Synthesis of Lactams via Isocyanide-Based Multicomponent Reactions

Pharande¹

2020

Synthesis

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Lactams are very important heterocycles as a result of their presence in a wide range of bioactive molecules, natural products and drugs, and also due their utility as versatile synthetic intermediates. Due to these reasons, numerous efforts have focused on the development of effective and efficient methods for their synthesis. Compared to conventional two-component reactions, multicomponent reactions (MCRs), particularly isocyanide-based MCRs, are widely used for the synthesis of a range of small heterocycles including lactam analogues. Despite their numerous applications in almost every field of chemistry, as yet there is no dedicated review on isocyanide-based multicomponent reactions (IMCRs) concerning the synthesis of lactams. Therefore, this review presents strategies towards the synthesis of α-, β-, γ-, δ- and ε-lactams using IMCRs or IMCRs/post-transformation reactions reported in the literature between 2000 and 2020.1 Introduction2 Developments in Lactam Synthesis2.1 α-Lactams2.2 β-Lactams2.3 γ-Lactams2.3.1 General γ-Lactams2.3.2 Benzo-Fused γ-Lactams2.3.3 Spiro γ-Lactams2.3.4 α,β-Unsaturated γ-Lactams2.3.5 Polycyclic Fused γ-Lactams2.4 δ-Lactams2.5 ε-Lactams3 Conclusions

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A Half‐Century of the Ugi Reaction: Classic Variant

Ullrich

Kazmaier

2023

Organic Reactions

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The classic Ugi reaction is a four‐component coupling process that involves a carboxylic acid, a carbonyl compound, an amine, and an isocyanide. All reaction components are in a dynamic equilibrium with several intermediates, until an irreversible intramolecular 1,4‐ O → N acyl transfer leads to the formation of an N ‐acylamino acid amide. If chiral components are used in this reaction, a mixture of diastereomers is generally formed with moderate‐to‐low stereoselectivity. The broad scope of substrates that can be used in the Ugi reaction allows for the straightforward synthesis of libraries of structurally related amino acid and peptide derivatives. Therefore, this methodology is often applied to the synthesis of drugs, drug‐like molecules, and natural products. This chapter describes different variations of classic Ugi reactions, including the use of functionalized and cleavable reaction components to illustrate the broad scope of the reaction. In addition, applications in target‐directed synthesis and comparisons to other related multicomponent reactions are presented. Tabular surveys are organized according to the isocyanides used. The literature is discussed from the first disclosure of an Ugi reaction in 1961 through to the end of 2012.

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A mild and efficient synthesis of monofluorinated α-lactam pseudopeptides via a novel dehydrofluorination of Ugi products

Abstract: Six novel monofluorinated α-lactam pseudopeptide derivatives were synthesized via Ugi reaction using gem-difluoromethylene-containing isocyanide as a key component, followed by dehydrofluorination of Ugi products in one pot without additional base.

Cited by 8 publications

References 29 publications

Expanding the substrate scope of ugi five-center, four-component reaction U-5C-4CR): ketones as coupling partners for secondary amino acids

Expanding the substrate scope of ugi five-center, four-component reaction U-5C-4CR): ketones as coupling partners for secondary amino acids

Synthesis of Lactams via Isocyanide-Based Multicomponent Reactions

A Half‐Century of the Ugi Reaction: Classic Variant

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