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Molbank, Volume 2024, Issue 4

December 2024 - 58 articles

Cover Story: The biomass derivative levoglucosenone and its reduced form Cyrene, which are obtained from the acid-catalyzed pyrolysis of cellulose, have emerged as promising chiral platform chemicals in materials chemistry and building blocks for the production of pharmaceuticals or natural products. Reports of fluorinated derivatives are limited; however, the incorporation of fluorine could be beneficial for the enantioselective synthesis of pharmaceuticals and natural products. We report a one-carbon difluorocyclopropanation/ring-expansion of Cyrene. The ring-enlargement was achieved by converting Cyrene into an enamine, reacting it with an in situ generated difluorocarbene, and then heating to open the cyclopropane ring. Access to the product provides access to a novel fluorinated analogue of this important chiral biomass pyrolysis product. View this paper
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Articles (58)

  • Communication
  • Open Access
1,016 Views
6 Pages

6 December 2024

Anilides of 3-oxo-4-phenylaminobutyric acid with Troc or COOEt protection at the phenylamino group undergo competing cyclization processes in neat polyphosphoric acid at 80 °C. Depending on the protecting group and the duration of the process, th...

  • Short Note
  • Open Access
1,033 Views
7 Pages

1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane

  • Jérémy Forté,
  • Patrick Herson and
  • Pascal Pigeon

6 December 2024

Ferrociphenols are anticancer organometallic molecules bearing a ferrocene group linked, at least, to one para-phenol moiety via a double bond. Up to the present, their biological activity has been thought to be linked to their oxidation within cells...

  • Short Note
  • Open Access
1,140 Views
4 Pages

5 December 2024

A highly efficient method has been developed for preparing 2-((3R,9bS)-5,5-dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one. This enantioenriched title compound was obtained via an organocatalytic asymmetric [3+2]-...

  • Short Note
  • Open Access
1,135 Views
4 Pages

4-(Benzoxazol-2-yl)phenyl 3-((3-Chloro-1,4-Naphthoquinon-2-yl)amino)phenyl Sulfate

  • Nadezhda V. Danilenko,
  • Mariia O. Lutsuk and
  • Andrei I. Khlebnikov

5 December 2024

New 4-(benzoxazol-2-yl)phenyl 3-((3-chloro-1,4-naphthoquinon-2-yl)amino)phenyl sulfate was synthesized via the SuFEx click reaction between fluorosulfate-containing 1,4-naphthoquinone and 2-(4-hydroxyphenyl)benzoxazole. 1,8-Diazabicyclo[5.4.0]undec-7...

  • Communication
  • Open Access
1 Citations
1,108 Views
5 Pages

5 December 2024

A one-carbon difluorocyclopropanation/ring-expansion has been developed for the chiral synthon Cyrene, which is obtained via cellulose pyrolysis. The ring-enlargement was achieved by converting Cyrene (dihydrolevoglucosenone) into an enamine, reactin...

  • Communication
  • Open Access
2,529 Views
14 Pages

3 December 2024

The wide range of application possibilities of fluorene derivatives, due to their unique physical and chemical properties, has made this class of molecules important for various disciplines. The synthesis of these compounds and the study of their pro...

  • Short Note
  • Open Access
1,868 Views
6 Pages

2-([1,1′-Biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3,3-dimethyl-3H-indole

  • Gabrielė Varvuolytė,
  • Aurimas Bieliauskas,
  • Neringa Kleizienė,
  • Asta Žukauskaitė and
  • Algirdas Šačkus

28 November 2024

The ligandless palladium-catalyzed Heck reaction of 4-ethenyl-3-methoxy-1-phenyl-1H-pyrazole and 2-([1,1′-biphenyl]-4-yl)-5-bromo-3,3-dimethyl-3H-indole gave the previously unreported 2-([1,1′-biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-...

  • Communication
  • Open Access
2 Citations
1,498 Views
10 Pages

Synthesis of N-p-Fluorothiosemicarbazone and of Bis(N-p-Fluorophenylthiourea): Crystal Structure and Conformational Analysis of N,N′-Bis(4-Fluorophenyl)Hydrazine-1,2-Bis(Carbothioamide)

  • Sirine Salhi,
  • Dorra Kanzari-Mnallah,
  • Isabelle Jourdain,
  • Michael Knorr,
  • Carsten Strohmann,
  • Jan-Lukas Kirchhoff,
  • Hédi Mrabet and
  • Azaiez Ben Akacha

28 November 2024

The reaction of the phosphonated hydrazone (2-hydrazineylidenepropyl) diphenylphosphine oxide 1 with p-fluorophenyl-isothiocyanate yields as a major product the thiosemicarbazone Ph2P(=O)CH2{C=N-NH(C=S)-N(H)C6H4F}CH3 (2-(1-(diphenylphosphoryl)propan-...

  • Communication
  • Open Access
1,556 Views
5 Pages

3-Methyl-2-(5-((trimethylsilyl)ethynyl)pyridin-2-yl)butan-2-ol

  • Oleg A. Mikhailov,
  • Almira R. Kurbangalieva and
  • Ilya D. Gridnev

27 November 2024

The reactions of dialkylzinc reagents with ketones are scarcely studied. In this paper, we describe a previously unknown direct alkylation of substituted 2-acetylpyridine with diisopropyl zinc, which gave a corresponding novel alcohol with 82% yield.

  • Short Note
  • Open Access
1,303 Views
7 Pages

Ammonium Oxathioamidate

  • M. Carla Aragoni,
  • David B. Cordes,
  • Anna Pintus,
  • Enrico Podda,
  • Riccardo Serra,
  • Alexandra M. Z. Slawin,
  • J. Derek Woollins and
  • Massimiliano Arca

26 November 2024

Ammonium oxathioamidate (1) was synthesised by the reaction between O-ethyl-thioxamate (oxalic acid-1-amide-2-O-ethyl ester) and ammonium hydrogen carbonate in water solution. Compound 1 was fully characterised by both microanalytical (elemental anal...

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Molbank - ISSN 1422-8599