The Synthesis of Carbapenem and Carbacephem Derivatives by a Combination of 4CC with the Chemistry of Oxazoles and N-boc-carbonamides

Neyer, Gebhard; Achatz, J.; Danzer, B.; Ugi, Ivar

doi:10.3987/com-89-s68

Cited by 18 publications

(1 citation statement)

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“…The use of low molecular weight alcohols or aprotic polar solvents has been shown to be advantageous in Ugi methodology hence the choice of methanol as the solvent. 7 Pirrung and Das Sarma noted that biphasic systems using aqueous media accelerate this type of reactions. 8 This was attempted, but we found that the convenience of removal of the methanol and immediate addition to the silica gel column for purification outweighed any advantage to the use of a biphasic system.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel β-lactams and in vitro evaluation against the human malaria parasite Plasmodium falciparum

Blackie

Feng²,

Smith³

et al. 2016

Arkivoc

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The use of three-component four-center Ugi reactions to afford the synthesis of novel β-lactams is described. Three series of compounds have been made using this reaction in combination with the Mannich reaction. All compounds formed are racemic mixtures and were tested against the chloroquine sensitive D10 strain of Plasmodium falciparum in an in vitro assay. All compounds showed low to moderate microMolar range activity with the most active compounds 2.6 and 3.1 showing IC 50 values 16 µM and 15 µM respectively

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Section: Resultsmentioning

confidence: 99%

Synthesis of novel β-lactams and in vitro evaluation against the human malaria parasite Plasmodium falciparum

Blackie

Feng²,

Smith³

et al. 2016

Arkivoc

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Ethyl Malonate

Bolton¹

2001

Encyclopedia of Reagents for Organic Synthesis

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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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The Synthesis of Carbapenem and Carbacephem Derivatives by a Combination of 4CC with the Chemistry of Oxazoles and N-boc-carbonamides

Cited by 18 publications

References 0 publications

Synthesis of novel β-lactams and in vitro evaluation against the human malaria parasite Plasmodium falciparum

Synthesis of novel β-lactams and in vitro evaluation against the human malaria parasite Plasmodium falciparum

Ethyl Malonate

A Half‐Century of the Ugi Reaction: Classic Variant

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