Hydroxylamine in der Vierkomponenten‐Kondensation nach Ugi, III

Zinner, G.; Hantelmann, O.

doi:10.1002/ardp.19753080502

Cited by 10 publications

(1 citation statement)

References 5 publications

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“…Continuing their studies, in 1974, Zinner et al 163 described an UT-4CR approach to 1,5-disubstituted tetrazoles using hydroxylamines as amine components. Reaction with formaldehyde in the presence of cyclohexyl isocyanide and hydrazoic acid (HN 3 ) afforded the corresponding 1,5-disubstituted tetrazole methylene hydroxylamines 50.…”

Section: Monocyclic Tetrazoles Derivativesmentioning

confidence: 99%

Tetrazoles via Multicomponent Reactions

2019

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Tetrazole derivatives are a prime class of heterocycles, very important to medicinal chemistry and drug design due to not only their bioisosterism to carboxylic acid and amide moieties but also to their metabolic stability and other beneficial physicochemical properties. Although more than 20 FDA-approved drugs contain 1H- or 2H-tetrazole substituents, their exact binding mode, structural biology, 3D conformations, and in general their chemical behavior is not fully understood. Importantly, multicomponent reaction (MCR) chemistry offers convergent access to multiple tetrazole scaffolds providing the three important elements of novelty, diversity, and complexity, yet MCR pathways to tetrazoles are far from completely explored. Here, we review the use of multicomponent reactions for the preparation of substituted tetrazole derivatives. We highlight specific applications and general trends holding therein and discuss synthetic approaches and their value by analyzing scope and limitations, and also enlighten their receptor binding mode. Finally, we estimated the prospects of further research in this field.

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Section: Monocyclic Tetrazoles Derivativesmentioning

confidence: 99%

Tetrazoles via Multicomponent Reactions

2019

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A Half‐Century of the Ugi Reaction: Modified Variants

Ullrich

Kazmaier

2023

Organic Reactions

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The classic Ugi reaction is a four‐component coupling process involving a carboxylic acid, a carbonyl compound, an amine, and an isocyanide, resulting in an N ‐acylamino acid amide product. Modified Ugi reactions employ special, often multifunctional, reaction components, and can involve fewer than or more than four components. This reaction exhibits broad scope and can be used to prepare complex heterocycles. As a result, this method has been employed to prepare diverse libraries of structurally related products, and in addition, is often applied to the synthesis of drugs, drug‐like molecules, and natural products. Applications in target‐directed synthesis are presented, as are comparisons to other related multicomponent reactions and heterocycle syntheses; modifications leading to achiral heteroaromatic ring systems are not included. This chapter covers the literature from the early days of the Ugi reaction in 1961 through the end of 2012.

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Multikomponentenreaktionen mit Isocyaniden

2000

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EinleitungOrganisch-chemische Synthesen haben einen hohen Grad an Kunstfertigkeit erlangt. Kaum ein komplizierter Naturstoff entzieht sich einer vielstufigen Totalsynthese. Dabei werden die Zielmoleküle oft mehr divergent als konvergent, also sequentiell, entsprechend ihrer Komplexität in vielen Schritten synthetisiert. Der Fortschritt in der Totalsynthese von Naturstoffen der vergangenen Jahrzehnte lässt sich beim Vergleich der Strychninsynthese von Woodward mit neueren Synthesen erkennen. [1] Er beruht z. T. auf der Optimierung von Syntheseoperationen und Reaktionen. Metallorganische Varianten klassischer Reaktionen sind häufig diastereo-, enantio-, regio-und/oder chemoselektiver und liefern die Produkte oft in besseren Ausbeuten. Verbesserte analytische sowie Trennmethoden tragen zu effizienteren Syntheseschritten bei. Während Woodward für seine 28-stufige Strychninsynthese 6 Â 10 À5 % Gesamtausbeute erhielt, konnten die Gruppen von Magnus, Overman, Kuehn und Rawal diese komplexe Verbindung in weniger Syntheseschritten und in 10 3 -bis 10 4 -mal höherer Gesamtausbeute herstellen.

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Hydroxylamine in der Vierkomponenten‐Kondensation nach Ugi, III

Cited by 10 publications

References 5 publications

Tetrazoles via Multicomponent Reactions

Tetrazoles via Multicomponent Reactions

A Half‐Century of the Ugi Reaction: Modified Variants

Multikomponentenreaktionen mit Isocyaniden

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