Macromol. Rapid Commun. 3/2014

Kreye, Oliver; Kugele, Dennis; Faust, Lorenz; Meier, Michael A. R.

doi:10.1002/marc.201470010

Cited by 9 publications

(14 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The use of multicomponent reactions in the field of organic chemistry, for instance in the synthesis of pharmaceuticals, 29 hydrogels, 30,31 peniciline 55 scaffolds 32 and peptidomimetics 33 is already well established. 32 Recently, the use of the P-3CR and the U-4CR in polymer chemistry was demonstrated by our [34][35][36][37][38][39] and other groups. [40][41][42][43] Furthermore, sequential Ugi reactions were studied by Wessjohann et al for the synthesis of peptide-peptoid 60 chimeras 31,44,45 and in the synthesis of macrocycles.…”

mentioning

confidence: 99%

Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

2015

Self Cite

View full text Add to dashboard Cite

The synthesis of sequence-defined oligomers by the iterative application of the modular Ugi four-component reaction (U-4CR) and the efficient thiol-ene addition reaction is described. By varying the amine component in the U-4CR, a sequence-defined and monodisperse tetramer (M = 1568.5 10 g/mol) was obtained. More interestingly, if both the amine and the isocyanide components were varied simultaneously in the U-4CR, a double sequence-controlled, monodisperse pentamer (M = 2411.8 g/mol) bearing ten different and selectable side chains was obtained. All oligomers were 15 thoroughly characterized by NMR and IR spectroscopy, mass spectrometry and GPC.One of the most challenging topics of modern polymer chemistry is the control over the monomer sequence in synthetic polymers. 1 These highly defined synthetic polymers exhibit novel material 20 properties and special self-assembly behaviour, depending on the monomer sequence. 2 However, the most sophisticated and controlled monomer sequences are synthesized by nature, for instance in translation and replication processes. 3 Over the past decades, different approaches have been developed in order to 25 synthesize sequence-defined polymers. 1,4 On the one hand, controlled radical polymerizations like RAFT, 5-7 ATRP 8-11 and NMP 11-13 can be applied for the synthesis of sequence-controlled polymers. 14 These radical polymerizations take advantage of simple one-pot procedures, but due to the radical nature of those 30 methods, side reactions, such as chain transfer, occur, thus chain to chain deviations are present. 15 On the other hand, stepwise procedures providing monodisperse macromolecules by using (DNA)-templates, [16][17][18][19][20][21] or complex molecular machines are reported. 22, 23 Although these approaches are elegant, the 35 synthetic efforts are considerable and the reactions can only be carried out on small scales. Recently, other protocols for the stepwise synthesis of sequence-defined polymers were reported making use of orthogonal reactions providing sequence-defined macromolecules by the iterative application of Michael additions 40 and aminolysis reactions, 24 azide-alkyne cycloadditions and amidifications, 25 or photochemical couplings and retro Diels-Alder reactions. 26 Our group focusses on the use of multicomponent reactions to achieve sequence control. 27 The iterative application of the Passerini three-component reaction 45

show abstract

mentioning

confidence: 99%

Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…Recently, ricinoleic acid has been used for the synthesis of different kinds of polymers, dendrimers and polyamides using the Passerini and Ugi multicomponent reactions. [42][43][44] Thus, the hybrid PHQ-fatty acids 12-17a-e were synthesised in good yields from the respective β-ketoesters 3a-e (Scheme 1, Table 2). The products 12-17a-e were purified using column chromatography and characterised by the usual spectroscopic methods, including infrared (IR) spectroscopy, in addition to proton ( 1 H NMR) and carbon ( 13 C NMR) nuclear magnetic resonance and CHN elemental analysis.…”

Section: Methodsmentioning

confidence: 99%

Multicomponent synthesis of novel hybrid PHQ-fatty acids

et al. 2015

View full text Add to dashboard Cite

Multicomponent reactions as methods for green synthesis are important pathways for obtaining of pharmacological compounds. In this work, an efficient synthesis of new fatty Hantzsch derivative compounds using a four-component reaction is described. We demonstrate for the first time a fatty acid polyhydroquinoline (hybrid PHQ-fatty acids) synthesis from renewable resources containing C16 and C18 saturated and unsaturated fatty chains, including the ricinoleic acid (12-hydroxy-9-cis-octadecenoic acid), the major constituent of castor oil. The experimental results demonstrate that the best value for charging the sulfamic acid was 20 mol% and that thirty new hybrids PHQ-fatty acids were synthesised in good yields.

show abstract

“…for preparation of a bistramide A segment [446], with allylic alcohols (followed by oxidation) for the preparation of γ-keto-α,β-unsaturated esters [447], with an alkene-dihydropyridone for preparation of the dihydrolycolucine skeleton [448], with vinyldioxolane derivatives [449], with alkenes connected to cellulose derivatives [450]; with fatty-acid derived alkene-carbamates for preparation of renewable polyesters and polyamides [451], with a passerine-derived triene for eventual dendrimer preparation (three-fold CM) [452],…”

Section: )mentioning

confidence: 99%

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Herndon

2016

Coordination Chemistry Reviews

View full text Add to dashboard Cite

Macromol. Rapid Commun. 3/2014

Cited by 9 publications

References 0 publications

Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

Multicomponent synthesis of novel hybrid PHQ-fatty acids

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Contact Info

Product

Resources

About