Tandem Michael addition of amines to maleic anhydride and 1,3-prototropic shift: experimental and theoretical results

Gurjar, Asha; Sinha, Pragya; Bansal, R. K.

doi:10.1016/j.tet.2014.06.003

Cited by 9 publications

(8 citation statements)

References 44 publications

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“…Neither the FTIR spectrum nor the 1 H NMR spectrum point to the occurrence of Michael addition of the glycine amine group to the methyl-substituted carboncarbon double bond, which is a well-known side reaction occurring during the imidization of maleic anhydride. 14 Synthesis and characterization of fully bio-based Diels-Alder adduct of glycine citraconimide and sorbic acid The renewable glycine citraconimide was reacted with sorbic acid, a naturally occurring substance used as a food preservative, 15 using Diels-Alder chemistry as described in the Experimental section and the reaction pathway is illustrated in Fig. 2.…”

Section: Resultsmentioning

confidence: 99%

“…The other impurities make up such a small amount that this is insignificant. Neither the FTIR spectrum nor the 1 H NMR spectrum point to the occurrence of Michael addition of the glycine amine group to the methyl‐substituted carbon–carbon double bond, which is a well‐known side reaction occurring during the imidization of maleic anhydride 14 …”

Section: Resultsmentioning

confidence: 99%

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Sustainable, rigid imide building blocks as promising substitutes for phthalic anhydride in alkyd resins

Hayden¹,

Papegaaij²,

Reuvers³

et al. 2020

Polymer International

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New, highly rigid bio-based building blocks were synthesized from renewable raw materials. In a first reaction step, an imide was made from citraconic anhydride and the amino acid glycine. This imide was subsequently reacted with sorbic acid using Diels-Alder chemistry, furnishing a double-ring structure. This new, very rigid renewable building block was then incorporated into alkyd resins by standard polycondensation chemistry and technology. The resulting, >80 wt% renewable, alkyd resins were evaluated as white paints in a preliminary way by solvent casting from xylene. The properties of the renewable coatings look promising, some even outperforming those of standard commercial alkyd resins. For further enhancing the sustainability of the systems discussed, turning these highly bio-based alkyd resins into stable aqueous emulsions is a must.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Sustainable, rigid imide building blocks as promising substitutes for phthalic anhydride in alkyd resins

Hayden¹,

Papegaaij²,

Reuvers³

et al. 2020

Polymer International

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“…Reaction of maleic anhydride with ammonia and primary amines can lead to maleimides, which are widely used for Michael addition of thiols or other nucleophiles onto the double bond. In principle, maleic anhydride can also act as substrate for this type of addition …”

Section: Part 2 – the Use Of Cyclic Anhydrides In Bioconjugate Chemistrymentioning

confidence: 99%

“…In principle, maleic anhydride can also act as substrate for this type of addition. 49 8.4. Maleic Anhydride-Derived Copolymers.…”

Section: ■ Introductionmentioning

confidence: 99%

Cyclic Anhydrides as Powerful Tools for Bioconjugation and Smart Delivery

Spanedda

Bourel-Bonnet

2021

Bioconjugate Chem.

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Cyclic anhydrides are potent tools for bioconjugation, therefore they are broadly used in the functionalization of biomolecules and carriers. The pH-dependent stability and reactivity, as well as the physical properties, can be tuned by the structure of the cyclic anhydride used, thus their application in smart delivery systems has become very important. This review intends to cover the last updates in the use of cyclic anhydrides as pH-sensitive linkers, their differences in reactivity and the latest applications found in bioconjugation chemistry, or chemical biology and when possible, in drug delivery.

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“…Some amino(‐imino)thiazolidinone derivatives exhibiting antifibrotic and anticancer activities have been successfully synthesized using a one‐pot multicomponent reaction strategy including [2+3] cyclocondensation and Knoevenagel condensation reactions [7] . The characteristic reactivity of maleic anhydride towards sulfur or nitrogen‐containing nucleophiles is a well‐known phenomenon and thia ‐Michael addition of sulfur based nucleophiles has been extensively studied [8,9] . When substituted thiourea derivatives are reacted with dimethyl acetylenedicarboxylate or acetylenedicarboxylic acid, corresponding five‐membered heterocyclic compounds are formed [10,11] .…”

Section: Introductionmentioning

confidence: 99%

An Efficient Ni(II) Laurate Promoted Heterocyclization of Symmetrical Thioureas with Maleic Anhydride and Mechanistic Approach toward Higher Substituted Thiazolidine‐4‐one‐5‐acetic Acids

Yıldırım

Öztürk

2022

ChemistrySelect

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For the first time, readily available Ni(II) laurate catalyzed thia‐Michael addition of symmetrical N,N‐disubstituted thioureas to maleic anhydride and subsequent cyclization in toluene afforded novel thiazolidine‐4‐one‐5‐acetic acids with good yields in a short reaction time. The efficiency and low cost of the renewable, eco‐friendly laurate based homogenous Lewis acid catalyst and the fact that cyclization proceeds in a much shorter time means that this synthetic method is interesting from a green chemistry point of view. The catalyst can be reused for many times without any significant loss of activity.

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Tandem Michael addition of amines to maleic anhydride and 1,3-prototropic shift: experimental and theoretical results

Cited by 9 publications

References 44 publications

Sustainable, rigid imide building blocks as promising substitutes for phthalic anhydride in alkyd resins

Sustainable, rigid imide building blocks as promising substitutes for phthalic anhydride in alkyd resins

Cyclic Anhydrides as Powerful Tools for Bioconjugation and Smart Delivery

An Efficient Ni(II) Laurate Promoted Heterocyclization of Symmetrical Thioureas with Maleic Anhydride and Mechanistic Approach toward Higher Substituted Thiazolidine‐4‐one‐5‐acetic Acids

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