Isonitrile, V. Erweiterter Anwendungsbereich der Passerini‐Reaktion

Ugi, Ivar; Meyr, Rudolf

doi:10.1002/cber.19610940844

Cited by 93 publications

(43 citation statements)

References 8 publications

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“…[13] Ugi and Meyr reported the first application of IMCRs to synthesize tetrazole derivatives in 1961. [14] They employed NaN 3 to replace the carboxylic acid in the 3-component Passerini reaction to give 1,5-disubstituted α-hydroxymethyl tetrazole derivatives. Afterwards, numerous tetrazole-fused structure-varied derivatives were synthesized by IMCRs to yield libraries of screening compounds applied in high-throughput screening.…”

Section: Introductionmentioning

confidence: 99%

α‐Amino Acid‐Isosteric α‐Amino Tetrazoles

Zhao

Kurpiewska

Kalinowska‐Tłuścik

et al. 2016

Chemistry A European J

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The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.

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Section: Introductionmentioning

confidence: 99%

α‐Amino Acid‐Isosteric α‐Amino Tetrazoles

Zhao

Kurpiewska

Kalinowska‐Tłuścik

et al. 2016

Chemistry A European J

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“…Several modifications of the classic Ugi 4CR have been described; these modifications involve the variation of one of the components or the introduction of a linkage between two of them, which leads to interesting potential druglike derivatives of the original aacylamino amide product. [4] Although a large number of modifications of the carboxylic acid reactant have been successfully explored (for example, water, [5] alcohol and carbon dioxide, [6] hydrazoic acid [7] ), the other components are less well suited to structural changes in view of the accepted mechanism of the Ugi 4CR. Isocyanide is the key reagent of the Ugi 4CR, and the carbonyl compound and the primary amine are required for the formation of the intermediate imine.…”

Section: In Memory Of Ivar Ugimentioning

confidence: 99%

A Mimicry of Primary Amines by Bis‐Secondary Diamines as Components in the Ugi Four‐Component Reaction

et al. 2006

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Splitting the amine! The Ugi four‐component reaction (Ugi 4CR) relies on the presence of a component with a primary amino group. This protocol has been modified by “splitting” the primary amine into two secondary amines. The resulting variant of the Ugi 4CR proceeds with good to excellent yield and widens the versatility of the original multicomponent reaction by enabling variation of the molecular backbone.

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“…The two most important isocyanide-based multicomponent reactions are the Passerini three-component reaction [13] to produce a-acyloxyamides, and the Ugi four-component reaction, which yields a-acylaminoamides. The Ugi reaction usually refers to the reaction between an amine (usually a primary or secondary amine), a carbonyl compound (aldehyde or ketone), an isocyanide, and a carboxylic acid [14].…”

Section: Introductionmentioning

confidence: 99%