,, ... und ehrt mir ihre Kunst!“ – Evaluierung historischer und neuer Synthesewege zu 1,5-Dihydroxy-6-oxo-1,6-dihydropyridin-2-carbonsäure und 1,3-Dihydroxy-2-oxo-3-pyrrolin-4-carbonsäure / “. . . and honour their art!” – Evaluation of Historical and New Routes to 1,5-Dihydroxy-6-oxo-1,6- dihydropyridine-2-carboxylic Acid and 1,3-Dihydroxy-2-oxo-3-pyrroline-4-carboxylic Acid

Wiedemann, Dennis; Grohmann, Andreas

doi:10.1515/znb-2009-11-1206

Cited by 6 publications

(2 citation statements)

References 10 publications

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“…A search of the Cambridge Structural Database (CSD Version 5.42, update of November 2020; Groom et al, 2016) for the 3hydroxy-1,5-dihydro-pyrrol-2-one fragment revealed 79 hits. Only 27 of these hits contain a fragment with the same structure as that of the title compound [refcodes: BOQXEN (del Corte et al, 2019), CIKPAQ (Sarkar et al, 2018), EVIYUD (Aliev et al, 2003b), GEJZAY (Mashevskaya et al, 2011), GIMGEQ (Sarkar et al, 2013), GITCAQ, GITDEV (Saha et al, 2017), IRUBUS (Aliev et al, 2003a), LIFBEJ, LIFBOT (Sun et al, 2011), NUXPIG (Wiedemann et al, 2009), PADHUA (Zonouz et al, 2015), PASTOT (Nicolaou et al, 2005), QIPNAH (Bhajammanavar et al, 2019), ROHNAG (Hosseinzadeh et al, 2019), TOMPER (Sakhno et al, 2008), UJEXOY (Ahankar et al, 2016), VILQEP (Gein et al, 2018), VIPNAJ (Mylari et al, 1991), VIQDOP (Guseinov et al, 2006), VOWGAP (Kazakov et al, 1990), WAPMIM (Dubovtsev et al, 2016), XINHIL (Aliev et al, 2001), XOKRAT, XOKRAT01 (Ramazani et al, 2019), YAJMOM (Wei et al, 2004), YIYFAP (Denislamova et al, 2014)]. All these structures and the title compound have the same electron density distribution within the 3-hydroxy-1,5-dihydropyrrol-2-one fragment.…”

Section: Database Surveymentioning

confidence: 99%

N-tert-Butyl-2-{2-[2-(4-chlorophenyl)-4-hydroxy-1-(5-methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-(4-methoxyphenyl)acetamido}-2-(4-methoxyphenyl)acetamide methanol monosolvate: single-crystal X-ray diffraction study and Hirshfeld surface analysis

Shyshkina¹,

Sakhno²,

Radchenko³

et al. 2021

Acta Cryst E

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The title compound, C36H37ClN4O7·CH3OH, which crystallizes as a methanol solvate, may possess biological activity, which is inherent for a natural peptide or protein. In the crystal, molecules of the title compound form hydrogen-bonded tetramers with the solvate molecules acting as bridges as a result of the O—H...O and N—H...O intermolecular hydrogen bonds. Hirshfeld surface analysis was used to study the different types of intermolecular interactions whose contributions are: H...H = 53.8%, O...H/H...O = 19.0%, C...H/H...C = 14.8%, Cl...H/H...Cl = 5.3%, N...H/H...N = 3.2%.

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Section: Database Surveymentioning

confidence: 99%

N-tert-Butyl-2-{2-[2-(4-chlorophenyl)-4-hydroxy-1-(5-methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-(4-methoxyphenyl)acetamido}-2-(4-methoxyphenyl)acetamide methanol monosolvate: single-crystal X-ray diffraction study and Hirshfeld surface analysis

Shyshkina¹,

Sakhno²,

Radchenko³

et al. 2021

Acta Cryst E

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“…Those from aldaric acids appear particularly attractive. The pathways via 2,5-dioxoadipic acid or 2,5-dihydroxymuconic acid as intermediates have been reported in the literature . They are, however, characterized by many reaction steps and low atom efficiency.…”

Section: Introductionmentioning

confidence: 99%

Facile Edge Functionalization of Graphene Layers with a Biosourced 2-Pyrone

Margani

Magrograssi

Piccini

et al. 2022

ACS Sustainable Chem. Eng.

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Edge functionalization of graphene layers is of great interest in the field of materials chemistry: the properties of graphene are substantially unaltered and its compatibility and chemical reactivity with various environments can be tuned. In this work, edge functionalization of graphene layers was performed with a 2-pyrone, ethyl 3-hydroxy-2-oxo-2H-pyran-6-carboxylate (Pyr-COOEt). 2-Pyrones are C-6 unsaturated heterocyclic sugar derivatives and are intriguing building blocks for the preparation of innovative chemical structures. Sodium 3-acetoxy-2-oxo-2Hpyran-6-carboxylate was prepared starting from mucic acid, in a one-pot synthesis with a yield of about 74%, and was then transformed into the acid and then into ethyl ester derivatives. The adduct of Pyr-COOEt with a high surface area graphite (HSAG) was obtained by simply mixing and donating energy, either thermal or mechanical. The functionalization yield was estimated from thermogravimetric analysis (TGA) data and was found to be up to 91%. The adducts were characterized by Fourier transform infrared and Raman spectroscopies and wide-angle X-ray diffraction. The presence of pyrone in the adduct was clearly detected in the IR spectra, and the bulk structure of the graphitic substrate was found to be substantially unaltered by the functionalization reaction. The experimental findings suggest that the edge functionalization of the graphene layers occurred. Stable water dispersions of HSAG/Pyr adducts were prepared and studied through ultraviolet−visible analysis. Aggregates of few-layer graphene were obtained by mild sonication and centrifugation, as revealed by high-resolution transmission electron microscopy. This paper shows that a biobased molecule can be used for selectively decorating the edges of graphene layers, with oxygenated functional groups having a defined chemical structure and avoiding the use of oil-based, dangerous, and even noxious ingredients. The most plausible interpretation for the formation of the HSAG adduct with 2-pyrone seems to be the cycloaddition reaction between the edges of the graphitic substrate and the unsaturated biomolecule. Such a functionalization appears to be suitable for a scale up and paves the way for the preparation of a variety of derivatives.

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ChemInform Abstract: “... and honour their art!” — Evaluation of Historical and New Routes to 1,5‐Dihydroxy‐6‐oxo‐1,6‐dihydropyridine‐2‐carboxylic Acid and 1,3‐Dihydroxy‐2‐oxo‐3‐pyrroline‐4‐carboxylic Acid.

Wiedemann

Grohmann

2010

ChemInform

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Cited by 6 publications

References 10 publications

N-tert-Butyl-2-{2-[2-(4-chlorophenyl)-4-hydroxy-1-(5-methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-(4-methoxyphenyl)acetamido}-2-(4-methoxyphenyl)acetamide methanol monosolvate: single-crystal X-ray diffraction study and Hirshfeld surface analysis

N-tert-Butyl-2-{2-[2-(4-chlorophenyl)-4-hydroxy-1-(5-methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-(4-methoxyphenyl)acetamido}-2-(4-methoxyphenyl)acetamide methanol monosolvate: single-crystal X-ray diffraction study and Hirshfeld surface analysis

Facile Edge Functionalization of Graphene Layers with a Biosourced 2-Pyrone

ChemInform Abstract: “... and honour their art!” — Evaluation of Historical and New Routes to 1,5‐Dihydroxy‐6‐oxo‐1,6‐dihydropyridine‐2‐carboxylic Acid and 1,3‐Dihydroxy‐2‐oxo‐3‐pyrroline‐4‐carboxylic Acid.

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