Erbium(III) Triflate: A Valuable Catalyst for the Synthesis of Aldimines, Ketimines, and Enaminones

Dalpozzo, Renato; Nino, Antonio De; Nardi, Mónica; Russo, Beatrice; Procopio, Antonio

doi:10.1055/s-2006-926378

Cited by 56 publications

(21 citation statements)

References 13 publications

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“…The high reactivity of a-alkylidene 5-membered cyclic carbonates (aCC) towards secondary amines [39][40][41] was exploited to design two novel bis(oxocarbamate) monomers, i. e. bis(2-methyl-3-oxobutan-2-yl) piperazine-1,4-dicarboxylate (M1) and bis(2methyl-3-oxobutan-2-yl) hexane-1,6-diylbis(methylcarbamate) (M2) following the reaction illustrated in Scheme 2. [40,41,43] Scheme 1. [40,42] DMACC was then reacted with piperazine or N,N-dimethyl-1,6-hexanediamine (DMHDA) in DMF at room temperature without any catalyst to provide the corresponding bis(oxocarbamate)s. It should be noted that primary diamines are not adapted to design bis(oxo-carbamate)s as it has previously been demonstrated that primary amines led to b-hydroxy-oxazolidinones by reaction with aCC.…”

Section: Resultsmentioning

confidence: 99%

CO₂‐Sourced Non‐Isocyanate Poly(Urethane)s with pH‐Sensitive Imine Linkages

et al. 2018

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Carbon dioxide is a renewable C1-feedstock that is exploited for the production of polymers. In this work, we report on the conversion of CO 2 into novel bis(oxo-carbamate)s that are then exploited for the synthesis of degradable non-isocyanate polyurethanes (NIPUs) bearing acid-sensitive imine functions within the polymer backbone. Two CO 2 -sourced bis(oxo-carbamate)s were first prepared by the facile catalyst-free and regioselective aminolysis of an a-alkylidene cyclic carbonate (prepared by carboxylative coupling of CO 2 with a propargylic alcohol) with two secondary diamines, piperazine and N,N'-dimethyl-1,6-hexanediamine. A large diversity of poly(urethane-co-imine)s (PUIs) with molar masses ranging from 4500 to 8500 g/mol were then prepared by polycondensation of bis(oxo-carbamate)s with various primary diamines, and by using Ti(OEt) 4 as catalyst and drying agent. Finally, the pH-responsiveness of PUIs was demonstrated by immersing a representative polymer in aqueous solutions at different pH. This work illustrates that hydrolytically degradable NIPUs can be constructed by polycondensation of novel CO 2 -sourced monomers with diamines.

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Section: Resultsmentioning

confidence: 99%

CO₂‐Sourced Non‐Isocyanate Poly(Urethane)s with pH‐Sensitive Imine Linkages

et al. 2018

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“…Possible mechanism for the formation of pyrrole is shown in the Scheme 2. We presume that initially pentane-2,4-dione 2 reacts with amine 3 to form the unsaturated amino ketone 5 and tautomerised to form intermediate 6 [29,30]. DABCO reacts with phenacyl bromide 1 and forms quaternary salt 7 [31], which subsequently react with intermediate 6 and form intermediate 8.…”

Section: Resultsmentioning

confidence: 99%

DABCO Promoted an Efficient and Convenient Synthesis of Pyrrole in Aqueous Medium

Meshram¹,

Bangade²,

Reddy³

et al. 2012

IJOC

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The synthesis of C-substituted and N-substituted pyrrole is described by the reaction of phenacyl bromides, pentane-2, 4-dione and amine in aqueous medium using DABCO as a catalyst. The method is very convenient and applicable for alkyl as well as aryl amines and phenacyl bromides. The procedure is amenable for the synthesis of new substituted pyrroles. Moreover, aqueous medium makes the method more eco-friendly

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“…Dalpozzo et al 15 utilizaram triflato de érbio(III) como catalisador na preparação de aldiminas, cetiminas e enaminonas. Exemplos representativos encontram-se no Esquema 3.…”

Section: Métodos De Preparaçãounclassified