Reaction of N-heterocyclic carbaldehydes with furanones – An investigation of reactivity and regioselectivity

Uhrner, Fabian; Lederle, Felix; Namyslo, Jan C.; Gjikaj, Mimoza; Schmidt, Andreas; Hübner, Eike G.

doi:10.1016/j.tet.2017.06.012

Cited by 5 publications

(4 citation statements)

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“…α-Angelica lactone has been identified as one of the key components from biomass to valuable chemical products [15]. Recently, we presented the synthesis of the N -donor functionalized ( E )-5-methyl-3-(( N -methylpyrazol-4-yl)methylene)furan-2-one ( 7 ) from α-angelica lactone [2]. Here, we investigated ring-opening of the lactone ring towards functionalized γ-hydroxycarboxylates.…”

Section: Resultsmentioning

confidence: 99%

“…As the tautomerism towards the keto-form prohibits the use of 10 as bifunctional comonomer, 7 was hydrogenated to 9 according to procedures given in literature [2]. Subsequent ring-opening of the lactone yields the sodium salt ( 3 ) of the corresponding γ-hydroxy-α-(arylmethyl)pentanoic acid in excellent yields of 98%.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of the precursors ( E )-5-methyl-3-(( N -methylpyrazol-4-yl)methylene)furan-2-one ( 7 ), 5-methyl-3-(( N -methylpyrazol-4-yl)methyl)dihydrofuran-2-one ( 9 ), and ( E )-3-benzylidendihydrofuran-2-one ( 6 ) has been performed according to our previous publication [2]. 3-Benzyldihydrofuran-2-one ( 8 ) has been prepared according to literature [14].…”

Section: Main Textmentioning

confidence: 99%

“…1b) [1]. Recently, we investigated the application of N -heterocyclic carboxaldehydes [2]. y-Butyrolactone or y-valerolactone can be used as starting materials, too and yield various derivatives [3–5].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of γ-hydroxy-α-(arylmethyl)carboxylic acids from lactones: pathway to a structural motif derived from lactic acid and amino acid analogs?

et al. 2019

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Objective A synthetic pathway to γ-hydroxy-α-(arylmethyl)carboxylic acids starting from α-angelica lactone and γ-butyrolactone was investigated. These γ-hydroxycarboxylic acids resemble structural motifs of lactic acid and amino acids. The possibility of cocondensation with lactic acid towards functionalized poly(lactic acid)s was analyzed. Results The functional γ-hydroxycarboxylates sodium 4-hydroxy-2-(( N -methylpyrazol-4-yl)methyl)pentanoate and sodium 4-hydroxy-2-(phenylmethyl)butanoate (2-benzyl-4-hydroxybutanoate) were synthesized in good yields as a proof of concept for the proposed reaction pathway. Additionally, sodium ( E )-2-(( N -methylpyrazol-4-yl)methylene)-4-oxopentanoate presenting an interesting structural motif was isolated. All products have been fully characterized by mass spectrometry, IR spectroscopy and 2D nuclear magnetic resonance (NMR) techniques. In contrast to the carboxylate anions, the corresponding carboxylic acids obtained after acidification were found to be unstable. The instability was analyzed by NMR experiments. With the help of diffusion ordered NMR spectroscopy, the cocondensation with lactic acid was elucidated. The reaction products were characterized as oligomers of pure lactic acid, while intramolecular condensation of the γ-hydroxycarboxylic acids prevents cocondensation with lactide. Electronic supplementary material The online version of this article (10.1186/s13104-019-4232-1) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%