Synthesis of Ecgoninic Acid and Related Pyrrolidones

Evans, George; Gray, Harold; Jacobson, H. W.

doi:10.1021/ja01162a104

Cited by 6 publications

(3 citation statements)

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“…However, the unsaturation of β-hydromuconic acid is not in the β-position, but in the γ-position relative to the EWGs, and is thereby less electron negative than in the previously described unsaturated esters. Nevertheless, several references describe the aza-Michael addition between primary and secondary amines and β-hydromuconic acid (Evans et al, 1950; Lavagnino and Ryan, 1983), and dimethyl β-hydromuconate (Wu et al, 1961). Interestingly, here also the cascade cyclization step to form the five-membered pyrrolidone ring is reported (Scheme 12, top).…”

Section: Future Potentialsmentioning

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: Future Potentialsmentioning

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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“…W e have found t h a t r e p l a c i n g t h e p r i m a r y amine r e a c t a n t ---C, 66.18,H,7.63;N,9.65 Found: C,65.75;H,7.32;N,9.70 256 TETRAHYDRO-1H-PYRROLO [ 1,2-d] [1,4] , 6.25;N, 9.65 Found: C, 61.88;H, 6.34;N, 9.64 I R (KBr): 3300, 3080, 2980N, 9.64 I R (KBr): 3300, 3080, , 2955N, 9.64 I R (KBr): 3300, 3080, , 1721N, 9.64 I R (KBr): 3300, 3080, , 1668N, 9.64 I R (KBr): 3300, 3080, , 1628N, 9.64 I R (KBr): 3300, 3080, , 1603N, 9.64 I R (KBr): 3300, 3080, , 1576N, 9.64 I R (KBr): 3300, 3080, , 1560N, 9.64 I R (KBr): 3300, 3080, , 1449N, 9.64 I R (KBr): 3300, 3080, , 1303N, 9.64 I R (KBr): 3300, 3080, , 1183MS mle 290 (M').…”

Section: -4mentioning

confidence: 99%

THE REACTION OFtrans-3-HEXENEDIOIC ACID WITH ETHYLENEDIAMINES. A SIMPLE ROUTE TO THE TETRAHYDRO-1H-PYRROLO[1,2-d][1,4]DIAZEPINE RING SYSTEM

Lavagnino

Ryan

1983

Organic Preparations and Procedures International

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“…However, the unsaturation of β-hydromuconic acid is not in the β-position, but in the γ-position relative to the EWGs, and is thereby less electron negative than in the previously described unsaturated esters. Nevertheless, several references describe the aza-Michael addition between primary and secondary amines and β-hydromuconic acid 70,71 , and dimethyl β-hydromuconate. 72 Interestingly, here also the cascade cyclization step to form the 5-membered pyrrolidone ring is reported (Scheme 4-15, top).…”

Section: Future Potentials Aza-michael Addition On Muconic Acidmentioning

confidence: 99%

Renewable cyclic monomers for high-performance biobased polyesters

Noordzij

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Synthesis of Ecgoninic Acid and Related Pyrrolidones

Cited by 6 publications

References 0 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

THE REACTION OFtrans-3-HEXENEDIOIC ACID WITH ETHYLENEDIAMINES. A SIMPLE ROUTE TO THE TETRAHYDRO-1H-PYRROLO[1,2-d][1,4]DIAZEPINE RING SYSTEM

Renewable cyclic monomers for high-performance biobased polyesters

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