Trimethyl Aconitate

Schäfer, Hans J.; Witthaut, Daniel; Kratschmer, Silke

doi:10.1002/047084289x.rn00999

Cited by 2 publications

(2 citation statements)

References 13 publications

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“…To the best of our knowledge the aza-Michael addition between an amine and trans -trimethyl aconitate, followed by the cascade cyclization step, has been reported only four times (Joentgen et al, 2002; Okada et al, 2009; Schäfer et al, 2009; Singh et al, 2016). All reported amines were primary mono-amines (e.g., benzylamine), to yield a N -substituted mono-pyrrolidone-dimethylcarboxylate, and found potential use as surfactant (Okada et al, 2009).…”

Section: Recent Developmentsmentioning

confidence: 99%

Cascade aza-Michael Addition-Cyclizations; Toward Renewable and Multifunctional Carboxylic Acids for Melt-Polycondensation

Noordzij

Wilsens

2019

Front. Chem.

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Although the aza-Michael addition reaction on various unsaturated (di-)carboxylic acids and esters of, for example, itaconic acid, is well-known, the consecutive cyclization reaction has not received much attention in literature. The products of this aza-Michael cascade reaction, being mono- or di-carboxylic acid or ester functionalized N-alkyl-pyrrolidone structures, prove interesting for melt-polycondensation reactions as they exhibit excellent stability at elevated temperatures. In other words, this reaction is a toolbox for the generation of renewable monomers and, in turn, polymers with tunable physiological properties. Therefore, this work provides an overview of the state-of-the-art of the cascade aza-Michael addition-cyclization reactions on biobased unsaturated acids and esters, and their use in polymerization reactions. Furthermore, we extend this overview with the cascade aza-Michael addition-cyclization reaction of trans-trimethyl aconitate with di-amines to form a tetra-functional N-alkyl-bis-(pyrrolidone dimethylcarboxylate), which exhibits excellent thermal stability and could effectively be used as monomer in polycondensation reactions. Importantly, the aza-Michael addition reaction between primary amines and trans-trimethyl aconitate can be considered a click-reaction; it proceeds quantitatively within minutes under ambient conditions and follows the principles of green chemistry.

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Section: Recent Developmentsmentioning

confidence: 99%

Cascade aza-Michael Addition-Cyclizations; Toward Renewable and Multifunctional Carboxylic Acids for Melt-Polycondensation

Noordzij

Wilsens

2019

Front. Chem.

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“…To the best of our knowledge the aza-Michael addition between an amine and transtrimethyl aconitate, followed by the cascade cyclization step, has been reported only four times. 28,[65][66][67] All reported amines were primary mono-amines (e.g. benzylamine), to yield a N-substituted mono-pyrrolidone-dimethylcarboxylate, and found potential use as surfactant.…”

Section: Recent Developments Aza-michael Addition On Aconitic Acidmentioning

confidence: 99%

Renewable cyclic monomers for high-performance biobased polyesters

Noordzij

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Trimethyl Aconitate

Cited by 2 publications

References 13 publications

Cascade aza-Michael Addition-Cyclizations; Toward Renewable and Multifunctional Carboxylic Acids for Melt-Polycondensation

Cascade aza-Michael Addition-Cyclizations; Toward Renewable and Multifunctional Carboxylic Acids for Melt-Polycondensation

Renewable cyclic monomers for high-performance biobased polyesters

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