Ugi/Robinson–Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

Shaw, Arthur Y.; Xu, Zhigang; Hulme, Christopher

doi:10.1016/j.tetlet.2012.02.030

Cited by 34 publications

(9 citation statements)

References 52 publications

(10 reference statements)

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“…Thus, we performed an U‐3CR on the indole‐based imines yielding compounds 14a – e . Then, utilizing phenyl glyoxal in a Passerini reaction, we were able to synthesize compound 15 which could be transformed to a variety of derivatives . In addition, we performed a Passerini reaction with keto‐carboxylic acids affording the corresponding γ‐ and δ‐lactone derivatives 16a , b .…”

Section: Resultsmentioning

confidence: 99%

Structure and Reactivity of Glycosyl Isocyanides

et al. 2018

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3D structural information was obtained from mono‐, di‐ and trisaccharide formamide and isocyanide derivatives by analysis of their X‐ray crystal structure and NMR spectroscopy. The isocyanide anomeric effect was observed. Data mining of the Cambridge Structural Database (CSD) was performed and statistically confirmed our findings. Application of the glycoside isocyanides in the synthesis of novel glycoconjugates as drug‐like scaffolds by MCR chemistry underscores the usefulness of the novel building blocks.

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Section: Resultsmentioning

confidence: 99%

Structure and Reactivity of Glycosyl Isocyanides

et al. 2018

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“…The conversion of Ugi product 133 to oxazole 135 was subsequently carried out via a debenzylation/ cyclodehydration protocol using (POCl 3 ), which led to the desired Robinson-Gabriel cyclodehydration reaction (Scheme 28). 75 In another interesting synthesis employing the Ugi reaction is the synthesis of aryloxazolone compounds, which are found in many potent non-steroidal drugs and found to be anti- A series of benzene/imidazole systems with more than three connected aromatic rings was synthesized using U-4CR through the condensation of terephthalic acid 44, c-hexylisocyanide 81 with n-butylamine 14, and phenylglyoxal hydrate 142 to afford Ugi adduct 143 followed by condensation with ammonia 144 to give the target compound 145 (Scheme 30). 78…”

Section: Synthesis Of Ve-membered Heterocyclic Compoundsmentioning

confidence: 99%

Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications

2020

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“…In contrast, Shaw et al [ 113 ] reported another convenient approach in which a sequential Ugi 4-CR followed by a Robinson–Gabriel reaction resulted in the desired oxazoles ( Scheme 44 ). Herein, dimethoxybenzylamine, several isocyanides, aryl-glyoxals and (hetero)-aryl carboxylic acids afforded the desired corresponding Ugi-products 144 in reasonable to good yields (42–65%).…”

Section: Reviewmentioning

confidence: 99%

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

Koopmanschap¹,

Ruijter²,

Orru³

2014

Beilstein J. Org. Chem.

230

117

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SummaryIn the recent past, the design and synthesis of peptide mimics (peptidomimetics) has received much attention. This because they have shown in many cases enhanced pharmacological properties over their natural peptide analogues. In particular, the incorporation of cyclic constructs into peptides is of high interest as they reduce the flexibility of the peptide enhancing often affinity for a certain receptor. Moreover, these cyclic mimics force the molecule into a well-defined secondary structure. Constraint structural and conformational features are often found in biological active peptides. For the synthesis of cyclic constrained peptidomimetics usually a sequence of multiple reactions has been applied, which makes it difficult to easily introduce structural diversity necessary for fine tuning the biological activity. A promising approach to tackle this problem is the use of multicomponent reactions (MCRs), because they can introduce both structural diversity and molecular complexity in only one step. Among the MCRs, the isocyanide-based multicomponent reactions (IMCRs) are most relevant for the synthesis of peptidomimetics because they provide peptide-like products. However, these IMCRs usually give linear products and in order to obtain cyclic constrained peptidomimetics, the acyclic products have to be cyclized via additional cyclization strategies. This is possible via incorporation of bifunctional substrates into the initial IMCR. Examples of such bifunctional groups are N-protected amino acids, convertible isocyanides or MCR-components that bear an additional alkene, alkyne or azide moiety and can be cyclized via either a deprotection–cyclization strategy, a ring-closing metathesis, a 1,3-dipolar cycloaddition or even via a sequence of multiple multicomponent reactions. The sequential IMCR-cyclization reactions can afford small cyclic peptide mimics (ranging from four- to seven-membered rings), medium-sized cyclic constructs or peptidic macrocycles (>12 membered rings). This review describes the developments since 2002 of IMCRs-cyclization strategies towards a wide variety of small cyclic mimics, medium sized cyclic constructs and macrocyclic peptidomimetics.

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Ugi/Robinson–Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

Cited by 34 publications

References 52 publications

Structure and Reactivity of Glycosyl Isocyanides

Structure and Reactivity of Glycosyl Isocyanides

Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

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