α,α-Dialkylglycines obtained by solid phase Ugi reaction performed over isocyanide functionalized resins

Aguiam, Nádia R.; Castro, Vânia I. B.; Ribeiro, Ana Isabel; Fernandes, Rui D. V.; Carvalho, Carina Martins; Costa, Susana P. G.; Pereira-Lima, Sílvia M. M. A.

doi:10.1016/j.tet.2013.08.002

Cited by 12 publications

(6 citation statements)

References 20 publications

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“…Scheme 27). Less hazardous dehydration conditions were applied by another research group [49]. Inexpensive aminomethyl PS resin was functionalized with an isocyano group, which was either directly generated on the resin (40, Scheme 7) or attached via a spacer (43).…”

Section: Methodsmentioning

confidence: 99%

“…Peptide formation on an isocyanide polymer support by U-4CC. α,α-Dialkylglycine, a highly hindered C-tetrasubstituted amino acid, was produced by U-4CR [49]. The reaction utilized isocyanide resin either without a linker or equipped with a linker (cf.…”

Section: Isocyanide Resinmentioning

confidence: 99%

“…The Petasis reactions were carried out in the solution phase and afforded trisubstituted α-amino acid 119, which was subjected to U-4CC. α,α-Dialkylglycine, a highly hindered C-tetrasubstituted amino acid, was produced by U-4CR [49]. The reaction utilized isocyanide resin either without a linker or equipped with a linker (cf.…”

Section: Isocyanide Resinmentioning

confidence: 99%

“…The scope of the reaction components is not limited to amine, aldehyde, carboxylic acid, and isocyanide-alternative reagents were successfully examined. For example, sulfonamide was used as an amine reagent [43], imine was directly bound to the Rink resin [44], or ketones were applied to replace the aldehydes despite their lower reactivity [45][46][47][48][49]. Alternatively, glyoxal was used as the aldehyde component in U-4CR, and the second carbonyl functionality was employed for the imidazole ring formation [50].…”

Section: Introductionmentioning

confidence: 99%

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Isocyanide Multicomponent Reactions on Solid Phase: State of the Art and Future Application

Cankařová

Krchňák

2020

IJMS

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Drug discovery efforts largely depend on access to structural diversity. Multicomponent reactions allow for time-efficient chemical transformations and provide advanced intermediates with three or four points of diversification for further expansion to a structural variety of organic molecules. This review is aimed at solid-phase syntheses of small molecules involving isocyanide-based multicomponent reactions. The majority of all reported syntheses employ the Ugi four-component reaction. The review also covers the Passerini and Groebke-Blackburn-Bienaymé reactions. To date, the main advantages of the solid-phase approach are the ability to prepare chemical libraries intended for biological screening and elimination of the isocyanide odor. However, the potential of multicomponent reactions has not been fully exploited. The unexplored avenues of these reactions, including chiral frameworks, DNA-encoded libraries, eco-friendly synthesis, and chiral auxiliary reactions, are briefly outlined.

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Section: Methodsmentioning

confidence: 99%

Section: Isocyanide Resinmentioning

confidence: 99%

Section: Isocyanide Resinmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Isocyanide Multicomponent Reactions on Solid Phase: State of the Art and Future Application

Cankařová

Krchňák

2020

IJMS

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“…[2, 18] We studied the Passerini reaction involving the isocyanide‐decorated polystyrene resin C (Figure 3), which was prepared from an aminomethylated polystyrene resin ( A ) using a published procedure 19. Coupling of the amine groups of A to formic acid with subsequent formamide dehydration yielded the resin C , as indicated by the formation of IR stretching bands at 1694 cm −1 ( B , formamide CO) and 2146 cm −1 ( C , isocyanide; For IR spectra, see the Supporting Information) 19b…”

Section: Methodsmentioning

confidence: 99%