Iodine-mediated synthesis of benzo[a]fluorenones from yne-enones

The chalcones derived from o-alkynylacetophenones and aromatic aldehydes (yne-enones) when heated under reflux with iodine in acetic acid gave a range of benzo[a]fluorenone derivatives in moderate to good yields. The transformation involves the formation of a vinyl indenone intermediate through regioselective alkyne hydration and intramolecular aldol condensation followed by electrocyclic ring closure and aromatization.

• Publication year

  2019

• Venue

  RSC Advances

• Publication date

  2019-07-29

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/c9ra02376cPMID 35530623PMCID 9069471
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Gold catalysis in total synthesis - recent achievements.

  2016cited by this paper
• Iron-Catalyzed Tandem Conia-Ene/Friedel-Crafts Reactions of o-Alkynyldihydrochalcones: Access to Benzo[b]fluorenes.

  2016cited by this paper
• Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes.

  2016cited by this paper
• Iodine‐Catalyzed Synthesis of Highly Functionalized 1H‐Indene Derivatives from Michael Adducts of o‐Alkynylarene Chalcones with Diethyl Malonate

  2015cited by this paper
• Iron(III) halide or iodine-promoted synthesis of 3-haloindene derivatives from o-alkynylarene chalcones

  2015cited by this paper
• Oxidative Gold Catalysis Meets Photochemistry – Synthesis of Benzo[a]fluorenones from Diynes

  2014cited by this paper
• Synthesis of Fully Substituted 3-Formyl-4-iodofurans via a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization/Iodination Cascade

  2014cited by this paper
• A Tandem Strategy for the Synthesis of 1H‐Benzo[g]indazoles and Naphtho[2,1‐d]isoxazoles from o‐Alkynylarene Chalcones

  2013cited by this paper
• Gold-catalyzed synthesis of iodofulvenes.

  2013cited by this paper
• Fluostatins I-K from the South China Sea-derived micromonospora rosaria SCSIO N160.

  2012cited by this paper
• Fused Benzo[b]fluorenols: Palladium‐Catalyzed Intramolecular Dehydroaromatization and Carbonyl Reduction

  2012cited by this paper
• AgOTf catalyzed hydration of terminal alkynes

  2012cited by this paper
• Molecular Iodine: An Efficient and Versatile Reagent for Organic Synthesis

  2012cited by this paper
• Copper-catalyzed intramolecular oxidative 6-exo-trig cyclization of 1,6-enynes with H2O and O2.

  2011cited by this paper
• An efficient route to tetrahydroindeno[2,1-b]pyrroles via a base-promoted reaction of (E)-2-alkynylphenylchalcone with 2-isocyanoacetate.

  2011cited by this paper
• When gold can do what iodine cannot do: A critical comparison

  2011cited by this paper
• Iodine-catalyzed transformation of molecules containing oxygen functional groups

  2011cited by this paper
• Fluostatins produced by the heterologous expression of a TAR reassembled environmental DNA derived type II PKS gene cluster.

  2010cited by this paper
• Cyclization of propargylic amides: mild access to oxazole derivatives.

  2010cited by this paper
• Exploiting the divergent reactivity of aryl-palladium intermediates for the rapid assembly of fluorene and phenanthrene derivatives.

  2009cited by this paper
• Brønsted Acid-promoted intramolecular carbocyclization of alkynals leading to cyclic enones.

  2009cited by this paper
• Efficient synthesis of fluoren-9-ones by the palladium-catalyzed annulation of arynes by 2-haloarenecarboxaldehydes.

  2008cited by this paper
• Total synthesis of isoprekinamycin: structural evidence for enhanced diazonium ion character and growth inhibitory activity toward cancer cells.

  2007cited by this paper
• Synthetic Use of Molecular Iodine for Organic Synthesis

  2006cited by this paper
• Fluostatins C∼E, Novel Members of the Fluostatin Family Produced by Streptomyces Strain Acta 1383 †

  2006cited by this paper
• Diazo group electrophilicity in kinamycins and lomaiviticin A: potential insights into the molecular mechanism of antibacterial and antitumor activity.

  2002cited by this paper
• Formation of benzo[b]fluorenes and the benzo[a]fluorene core of the fluostatins by cyclization of diaryldiynones.

  2001cited by this paper
• Convenient preparation of 11H-benzo[a]fluorenone and 11H-benzo[b]fluorenone

  1988cited by this paper
• Synthesis of Pyranones and Benzofluorenones from Ketones and Carboxylic Acids1

  1961cited by this paper
• USE OF IODINE AS A DEHYDRATING AND CONDENSING AGENT.

  1915cited by this paper

• TfOH-Mediated Cascade Cyclization of Conjugated Enynes to Access Benzofluorenones.

  2025cites this paper
• Divergent Aromatization of α-Halobenzyl γ-Butenolides Initiated by Selective Enol Protonation to Benzo[c]fluorenones and Naphthalenes.

  2024cites this paper
• Divergent synthesis of 3,4-dihydro-2H-benzo[h]chromen-2-one and fluorenone derivatives from ortho-alkynylarylketones.

  2023cites this paper
• Radical Tandem Bicyclization Triggered by the α-Position of α,β-Unsaturated Ketones Bearing Nonterminal 1,6-Enynes: Synthesis of the 5H-Benzo[a]fluoren-5-one Skeleton.

  2020cites this paper
• Iodine-catalyzed efficient synthesis of xanthene/thioxanthene-indole derivatives under mild conditions

  2020cites this paper