Reactivity of polyhydroxyalkyl-heterocycles towards Lewis acids

Vargas, Ângelo; Fernández-Bolaños, José G.; Fuentes, José; Robina, Inmaculada

doi:10.1016/s0957-4166(01)00568-7

Cited by 14 publications

(5 citation statements)

References 48 publications

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“…As shown in Scheme 1, methyl 2‐methyl‐5‐(1,2,3,4‐tetrahydroxybutyl)‐1H‐pyrrole‐3 carboxylate (compound 2 ) and methyl 5‐formyl‐2‐methyl‐1H‐pyrrole‐3‐carboxylate (compound 3 ) were prepared according to the literature [23,47].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and pyrolysis of two novel pyrrole ester flavor precursors

Fan

Chu

Tian

et al. 2022

Journal of Heterocyclic Chem

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In order to develop the high‐temperature‐released pyrrole aroma, two novel flavors precursors of methyl 2‐methyl‐5‐(((2‐methylbutanoyl)oxy)methyl)‐1‐propyl‐1H‐pyrrole‐3‐carboxylate and methyl 2‐methyl‐5‐(((2‐methylbutanoyl)oxy)methyl)‐1‐propyl‐1H‐pyrrole‐3‐carboxylate were synthesized using glucosamine hydrochloride and methyl acetoacetate as raw materials through cyclization, oxidation, alkylation, reduction, and esterification. The target compounds were characterized by nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high‐resolution mass spectrometry (HRMS). Thermogravimetry (TG), differential scanning calorimeter (DSC) and the pyrolysis‐gas chromatography/mass spectrometry (Py‐GC/MS) methods were used to analyze the heating‐stability of the target compounds, and the pyrolysis mechanism was inferred. Py‐GC/MS results indicated that some fragrance compounds were formed during thermal degradation such as 2‐methylbutyric acid, 2‐methylbutyrate, alkylpyrroles, and benzoic acid, which were important aroma components or flavor additives. This provided a theoretical reference for the application of pyrrole ester in cigarette and heat‐processed food flavoring.

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Section: Resultsmentioning

confidence: 99%

Synthesis and pyrolysis of two novel pyrrole ester flavor precursors

Fan

Chu

Tian

et al. 2022

Journal of Heterocyclic Chem

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“…The reaction showed no concurrent side reaction, which confirmed the excellent regioselectivity of the cleavage. The yield of the reaction is remarkably higher with Eco‐Mn Ox1 than with Ce(IV) reagents, which require a large excess of oxidant (11 equivalents, 48 % yield) . This oxidative cleavage of polyhydroxyalkyl furan to furan aldehyde could be an interesting way to produce functionalized furfural compounds, with new functionalities compared to the widely studied furfural compounds …”

Section: Reactivity Of Eco‐mn Catalystsmentioning

confidence: 97%

“…The yield of the reaction is remarkably higher with Eco-Mn Ox1 than with Ce(IV) reagents, which require a large excess of oxidant (11 equivalents, 48 % yield). [72] This oxidative cleavage of polyhydroxyalkyl furan to furan aldehyde could be an interesting way to produce functionalized furfural compounds, with new functionalities compared to the widely studied furfural compounds. [73,74] This method can easily replace toxic or unstable oxidants such as NaIO 4 , Pb(OAc) 4 , NaBiO 3 , sodium and calcium hypochlorite, Ce(IV), Cr(VI), Co(II) or V(IV) reagents, Niodosuccinimide.…”

Section: Eco-mn Ox1 Catalyst a Versatile Oxidative Agent Of Alcoholsmentioning

confidence: 99%

Eco‐Mn Ecocatalysts: Toolbox for Sustainable and Green Lewis Acid Catalysis and Oxidation Reactions

et al. 2020

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Phytoextraction is one of the most promising phytotechnologies used to restore natural environments degraded by mining activities. In New Caledonia, a few plant species, which belong to the Grevillea genus, have the ability to extract Mn from soil and accumulate it in abundance (over 1 % of leaves dry weight). This review describes the use of Grevillea Mn‐accumulating plant species to produce the first bio‐sourced Mn catalysts, called Eco‐Mn catalysts. Extensive structural studies of Eco‐Mn catalysts have highlighted an original composition characteristic of their vegetal origin. Eco‐Mn catalysts have demonstrated competitive catalytic activities compared to conventional Mn catalysts in Lewis acid catalysis, aminoreductions, alcohol oxidations, epoxidation reactions, oxidative cleavage of 1,2‐diols and alkenes and “Janus catalysts” for sequential tandem oxidations such as tandem carbonyl‐ene cyclisation, synthesis of substituted pyridines and oxidative iodination of ketones.

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“…Hydrogenolysis of 14a led to a complex mixture of compounds resulting from hydrogenolysis of benzyl ethers and from the furan moiety and the partial debenzylation of benzyl ethers. Other debenzylation procedures led to the formation of undesired products . Hetarylene aminopolyol 15 was then successfully obtained applying a coupling reaction (18 h) between 6b and 13b with subsequent deprotetion with TBAF in THF.…”

Section: Resultsmentioning

confidence: 99%