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9 article(s) from Heimgartner, Heinz

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

Greta Utecht-Jarzyńska,
Karolina Nagła,
Grzegorz Mlostoń,
Heinz Heimgartner,
Marcin Palusiak and
Marcin Jasiński

Full Research Paper
Published 28 Jun 2021

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1. Graphical Abstract
2. Figure 1: Structures of exemplary benzo- and heteroaromatic fused 1,4-quinone drugs and natural products.
  
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3. Scheme 1: First [3 + 2]-cycloaddition of 1,4-naphthoquinone (1a) with intermediate nitrile imine 2, generated...
  
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4. Scheme 2: Selected applications of trifluoroacetonitrile imines 7 in the synthesis of S-containing 5- and 6-m...
  
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5. Scheme 3: Synthesis of [3 + 2]-cycloadducts 9a–l derived from CF₃-substituted nitrile imines 7a–h and 1,4-qui...
  
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6. Figure 2: X-ray structure of 3-trifluoromethylpyrazole derivative 9d. The labeling scheme of the asymmetric u...
  
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7. Scheme 4: Thermal elimination of MeOH from the initial [3 + 2]-cycloadduct of 1d and nitrile imine 7d generat...
  
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8. Scheme 5: Formation of the thermally stable, initially formed [3 + 2]-cycloadduct 10c obtained from 1e and ni...
  
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9. Figure 3: Electronic absorption spectra for selected a) naphthoquinone-derived (9c, 9d, 9g) and b) anthraquin...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

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Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts

Grzegorz Mlostoń,
Małgorzata Celeda,
Katarzyna Urbaniak,
Marcin Jasiński,
Vladyslav Bakhonsky,
Peter R. Schreiner and
Heinz Heimgartner

Full Research Paper
Published 19 Feb 2019

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1. Graphical Abstract
2. Scheme 1: Synthesis of 2-unsubstituted imidazole N-oxides 1 from α-hydroxyiminoketones 2 and formaldimines 3.
  
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3. Scheme 2: Preparation of adamantyloxyamine (4) and its conversion into N-(adamantyloxy)formaldimine (6a); Ad ...
  
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4. Scheme 3: Synthesis of 1-(adamantyloxy)imidazole 3-oxides 7a–e and 1-adamantylimidazole 3-oxides 7f,g in acet...
  
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5. Scheme 4: Deoxygenation of 1-(adamantyloxy)imidazole 3-oxides 7a–d and isomerization of 7b into imidazole-2-o...
  
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6. Scheme 5: Conversions of imidazole 3-oxides 7a–d into 1-(adamantyloxy)imidazole-2-thiones 10a–d via sulfur tr...
  
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7. Scheme 6: Syntheses of the non-symmetric 1,3-dialkoxyimidazolium bromides 13a–c and 1-alkyl-3-alkoxyimidazoli...
  
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8. Scheme 7: Attempted O-adamantylation of imidazole N-oxide 7a with adamantan-1-yl trifluoroacetate and subsequ...
  
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9. Scheme 8: Synthesis of the symmetric 1,3-di(adamantyloxy)imidazolium bromide (15) and its transformation to 1...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2019, 15, 497–505, doi:10.3762/bjoc.15.43

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First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

Grzegorz Mlostoń,
Katarzyna Urbaniak,
Paweł Urbaniak,
Anna Marko,
Anthony Linden and
Heinz Heimgartner

Full Research Paper
Published 19 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Reactions of aryl/hetarylthiochalcones 1a–d with 1,4-naphthoquinone (2b).
  
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3. Scheme 2: Reactions of thiochalcones 1a–d with 1,4-anthraquinones 2c and 2d.
  
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4. Figure 1: ORTEP plot [29] of the molecular structure of 4k showing the major conformation of the disordered thiop...
  
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5. Figure 2: Products of the reactions of thiochalcones 1a and 1b with 1,4-benzoquinone (2a) and of 1a with mena...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2018, 14, 1834–1839, doi:10.3762/bjoc.14.156

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Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies

Grzegorz Mlostoń and
Heinz Heimgartner

Review
Published 24 Oct 2017

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1. Graphical Abstract
2. Figure 1: Dialkyl dicyanofumarates E-1 and dicyanomaleates Z-1.
  
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3. Scheme 1: Methods for the synthesis of dialkyl dicyanofumarates E-1 from alkyl cyanoacetates 2.
  
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4. Scheme 2: Methods for the synthesis of dialkyl dicyanofumarates E-1 from alkyl bromoacetates 3.
  
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5. Scheme 3: Reaction of dimethyl dicyanofumarate (E-1b) with dimethoxycarbene [(MeO)₂C:] generated in situ from...
  
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6. Scheme 4: Cyclopropanation of diethyl dicyanofumarate (E-1a) through reaction with the thiophene derived sulf...
  
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7. Scheme 5: Cyclopropanation of dimethyl dicyanofumarate (E-1b) through a stepwise reaction with the in situ ge...
  
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8. Scheme 6: The [2 + 2]-cycloadditions of dimethyl dicyanofumarate (E-1b) with electron-rich ethylenes 20 and 22...
  
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9. Scheme 7: The [2 + 2]-cycloaddition of isomeric dimethyl dicyanofumarate (E-1b) and dicyanomaleate (Z-1b) wit...
  
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10. Scheme 8: Non-concerted [2 + 2]-cycloaddition between E-1b and bicyclo[2.1.0]pentene (27).
  
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11. Scheme 9: Stepwise [3 + 2]-cycloadditions of some thiocarbonyl S-methanides with dialkyl dicyanofumarates E-1...
  
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12. Scheme 10: Stepwise [3 + 2]-cycloadditions of dimethyl dicyanofumarate (E-1b) and dimethyl dicyanomaleate (Z-1b...
  
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13. Scheme 11: [3 + 2]-Cycloaddition of diazomethane with dimethyl dicyanofumarate (E-1b) leading to 1H-pyrazole d...
  
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14. Scheme 12: Reversible Diels–Alder reaction of fulvenes 36 with diethyl dicyanofumarate (E-1a).
  
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15. Scheme 13: [4 + 2]-Cycloaddition of 9,10-dimethylanthracene (39b) and E-1a.
  
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16. Scheme 14: Stepwise [4 + 2]-cycloaddition of dimethyl dicyanofumarate (E-1b) with electron-rich 1,1-dimethoxy-...
  
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17. Scheme 15: Formal [4 + 2]-cycloaddition of 3,4-di(α-styryl)furan (47) with dimethyl dicyanofumarate (E-1b).
  
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18. Scheme 16: Acid-catalyzed Michael addition of enolizable ketones of type 49 to E-1.
  
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19. Scheme 17: Reaction of diethyl dicyanofumarate (E-1a) with ammonia NH₃.
  
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20. Scheme 18: Reaction of dialkyl dicyanofumarates E-1 with primary and secondary amines.
  
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21. Scheme 19: Reaction of dialkyl dicyanofumarates E-1 with 1-azabicyclo[1.1.0]butanes 55.
  
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22. Scheme 20: Formation of pyrazole derivatives in the reaction of hydrazines with E-1.
  
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23. Scheme 21: Formation of 5-aminopyrazole-3,4-dicarboxylate 65 via heterocyclization reactions.
  
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24. Scheme 22: Reactions of aryl- and hetarylcarbohydrazides 67 with E-1a.
  
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25. Scheme 23: Multistep reaction leading to perhydroquinoxaline derivative 73.
  
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26. Scheme 24: Synthesis of ethyl 7-aminopteridin-6-carboxylates 75 via a domino reaction.
  
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27. Scheme 25: Synthesis of morhpolin-2-ones 80 from E-1 and β-aminoalcohols 78 through an initial aza-Michael add...
  
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28. Scheme 26: Reaction of 3-amino-5-arylpyrazoles 81 with dialkyl dicyanofumarates E-1 via competitive nucleophil...
  
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29. Scheme 27: Heterocyclization reaction of thiosemicarbazone 86 with E-1a.
  
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30. Scheme 28: Formation of diethyl 4-cyano-5-oxotetrahydro-4H-chromene-3,4-dicarboxylate (90) from E-1a via heter...
  
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31. Scheme 29: Reaction of dialkyl dicyanofumarates E-1 with cysteamine (92).
  
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32. Scheme 30: Formation of disulfides through reaction of thiols with E-1a.
  
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33. Scheme 31: Formation of CT salts of E-1 with Mn²⁺ and Cr²⁺ metallocenes through one-electron transfer.
  
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34. Scheme 32: Oxidation of diethyl dicyanofumarate (E-1a) with H₂O₂ to give oxirane 101.
  
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35. Scheme 33: The aziridination of E-1b through nitrene addition.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2017, 13, 2235–2251, doi:10.3762/bjoc.13.221

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A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

Grzegorz Mlostoń,
Paulina Pipiak,
Róża Hamera-Fałdyga and
Heinz Heimgartner

Full Research Paper
Published 08 Sep 2017

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1. Graphical Abstract
2. Scheme 1: Reactions of diphenyl and phenyl selenophen-2-yl thioketones with diazomethane (CH₂N₂; Sel = seleno...
  
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3. Scheme 2: Reaction of diaryl thioketones with trimethylsilyldiazomethane (TMS-CHN₂).
  
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4. Scheme 3: Formation of tetraaryl/hetarylethenes 9 from the reaction of TMS-CHN₂ with diaryl/hetaryl thioketon...
  
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5. Scheme 4: Synthesis of dibenzofulvenes 9g–k.
  
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6. Scheme 5: a) Mechanistic explanation for formation of ethenes 9 from dithiolanes of type 6 and b) desilylatio...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2017, 13, 1900–1906, doi:10.3762/bjoc.13.185

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Dimerization reactions of aryl selenophen-2-yl-substituted thiocarbonyl S-methanides as diradical processes: a computational study

Michael L. McKee,
Grzegorz Mlostoń,
Katarzyna Urbaniak and
Heinz Heimgartner

Full Research Paper
Published 03 Mar 2017

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1. Graphical Abstract
2. Scheme 1: Generation and typical reactions of the reactive dialkyl and diaryl thiocarbonyl S-methanides 1.
  
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3. Figure 1: Structures of the reactive intermediates as a diradical 6 or a zwitterion 7 in the course of the di...
  
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4. Scheme 2: The in situ generation of phenyl selenophen-2-yl S-methanide (8) and its competitive reactions: 1,3...
  
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5. Figure 2: Potential 1,3-dipolar electrocyclization of thiocabonyl S-methanide 8A. Computed enthalpies (free e...
  
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6. Figure 3: Stepwise radical dimerization of the reactive thiocarbonyl S-methanide 8. Computed enthalpies (free...
  
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7. Figure 4: Potential competitive cyclization reactions of the intermediate diradical 12.
  
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8. Figure 5: a) Spin densities in the conformers 12F and 12G of diradical 12. b) Heteroatom effect on the magnit...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2017, 13, 410–416, doi:10.3762/bjoc.13.44

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Synthesis of ferrocenyl-substituted 1,3-dithiolanes via [3 + 2]-cycloadditions of ferrocenyl hetaryl thioketones with thiocarbonyl S-methanides

Grzegorz Mlostoń,
Róża Hamera-Fałdyga,
Anthony Linden and
Heinz Heimgartner

Full Research Paper
Published 08 Jul 2016

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1. Graphical Abstract
2. Scheme 1: Reactions of aromatic thiocarbonyl S-methanides 2a,b with ferrocenyl thioketones 1 (Table 1).
  
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3. Figure 1: ORTEP Plot [16] of the molecular structures of the ferrocenyl-substituted 1,3-dithiolanes 5b and 5f (wi...
  
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4. Scheme 2: Reactions of cycloaliphatic thiocarbonyl S-methanides with ferrocenyl hetaryl thioketones 1 (Table 1).
  
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5. Scheme 3: Reaction of 3c with ferrocenyl methyl thioketone 1e.
  
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6. Scheme 4: Mesomeric stabilization of the 1,5-diradical intermediate in the reaction of aromatic thiocarbonyl S...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2016, 12, 1421–1427, doi:10.3762/bjoc.12.136

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Diradical reaction mechanisms in [3 + 2]-cycloadditions of hetaryl thioketones with alkyl- or trimethylsilyl-substituted diazomethanes

Grzegorz Mlostoń,
Paulina Pipiak and
Heinz Heimgartner

Full Research Paper
Published 14 Apr 2016

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1. Graphical Abstract
2. Scheme 1: ‘Head-to-head dimerization’ of diarylthioketone S-methanides 3a,b leading to 2,2,3,3-tetrasubstitut...
  
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3. Scheme 2: Diradical nature of the reactive intermediate 3c in the reaction of phenyl selenophen-2-yl thioketo...
  
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4. Scheme 3: Formation of thiiranes 8 and/or 1,3-dithiolanes 10 in the reaction of aryl/aryl, aryl/hetaryl and d...
  
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5. Scheme 4: Proposed competitive mechanisms in the reactions of aryl/hetaryl and dihetaryl thioketones 1 with 2...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2016, 12, 716–724, doi:10.3762/bjoc.12.71

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Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

Grzegorz Mlostoń,
Paulina Grzelak,
Maciej Mikina,
Anthony Linden and
Heinz Heimgartner

Full Research Paper
Published 28 Apr 2015

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1. Graphical Abstract
2. Scheme 1: Hetero-Diels–Alder reaction of thiobenzophenone (1a) with dimethyl acetylenedicarboxylate (2a) [10].
  
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3. Scheme 2: Synthesis of polycyclic thiopyrans via the hetero-Diels–Alder reaction/1,3-hydrogen shift sequence.
  
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4. Figure 1: ORTEP Plot [19] of the molecular structure of 4b, drawn using 50% probability displacement ellipsoids.
  
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5. Scheme 3: Reactions of aryl/hetaryl thioketones with methyl propiolate (Table 1).
  
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6. Scheme 4: Oxidation of selected thiopyrans 4 and 5 to give the corresponding sulfones.
  
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7. Figure 2: ORTEP Plot [19] of the molecular structure of one of the symmetry-independent molecules of 6d, drawn us...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2015, 11, 576–582, doi:10.3762/bjoc.11.63

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