18357-35-2

Usage

Type

Synthetic organic compound

Class

Pyranones

Derivative of

Pyran-4-one

Characterized by

Presence of two 4-methylphenyl groups at 2 and 6 positions of pyran-4-one ring

Commonly used in

Organic synthesis

Applications in

Pharmaceutical and agrochemical industries

Known for

Aromatic and heterocyclic properties

Structure lends itself to

Potential biological and pharmacological activities

Subject of interest for

Further research and development

Upstream product

• 63499-66-1 1,6-bis(4-methylphenyl)hexane-1,3,4,6-tetraone 
• 36200-40-5 1,5-bis(4-methylphenyl)-1,3,5-pentane-trione 
• 34793-64-1 1,5-di-(p-methylphenyl)-1,4-pentadiyn-3-one 
• 766-97-2 4-n-methylphenylacetylene 
• 27835-00-3 ethyl (4-methylbenzoyl)acetate 
• 13422-78-1 3-oxo-3-p-toluoylpropanoic acid 
• 866913-73-7 1,5-di-p-tolylpenta-1,4-diyn-3-ol 
• 145489-52-7 3-<2-aminophenylimino(p-toluoyl)>-4-hydroxy-6-(p-tolyl)-2H-pyran-2-one 
• 65384-67-0 4-hydroxy-3-(4-methylbenzoyl)-6-(4-methylphenyl)-2H-pyran-2-one 

Downstream Products

• 1268633-97-1 2,6-bis[3-(N-2-(S)-propanolaminosul;fonyl)-4-methylphenyl]-4H-pyran-4-one 
• 1268633-98-2 2,6-bis[3-(N,N-di-ethylaminosulfonyl)-4-methylphenyl]-4H-pyran-4-one 
• 1268633-99-3 2,6-bis[3-(N,N-di-propylaminosulfonyl)-4-methylphenyl]-4H-pyran-4-one 
• 1268634-00-9 2,6-bis[3-(N,N-di-2-ethanolaminosulfonyl)-4-methylphenyl]-4H-pyran-4-one 
• 1268634-01-0 2,6-bis[4-methyl-3-(pyrrolidin-1-ylsulfonyl)phenyl]-4H-pyran-4-one 
• 1268634-02-1 2,6-bis[4-methyl-3-(piperidin-1-ylsulfonyl)phenyl]-4H-pyran-4-one 
• 1268634-03-2 2,6-bis[4-methyl-3-(morpholin-4-ylsulfonyl)phenyl]-4H-pyran-4-one 
• 1268634-04-3 2,6-bis[4-methyl-3-(phenylaminosulfonyl)phenyl]4H-pyran-4-one 
• 1268634-05-4 2,6-bis[4-methyl-3-(3-methyl-1H-pyrazol-1-ylsulfonyl)phenyl]-4H-pyran-4-one 
• 1268634-06-5 2,6-bis[3-(methoxysulfonyl)-4-methyl]-4H-pyran-4-one 
• 1268634-07-6 2,6-bis[3-(ethoxysulfonyl)-4-methylphenyl]4H-pyran-4-one 
• 1268634-08-7 2,6-bis[3-(propoxysulfonyl)-4-methylphenyl]-4H-pyran-4-one 
• 1268634-09-8 2,6-bis[3-(butoxysulfonyl)-4-methylphenyl]-4H-pyran-4-one 
• 1268634-10-1 2,6-bis[3-(isobutoxysulfonyl)-4-methylphenyl]-4H-pyran-4-one 

Relevant academic research and scientific papers

Photoinduced Aerobic Iodoarene-Catalyzed Spirocyclization of N-Oxy-amides to N-Fused Spirolactams**

Iodoarene catalysis is a powerful methodology that usually requires an excess of oxidant, or of redox mediator if the terminal oxidant is dioxygen, to generate the key hypervalent iodine intermediate to proceed efficiently. We report that, using the spiro-cyclization of amides as a benchmark reaction, aerobic iodoarene catalysis can be enabled by relying on a pyrylium photocatalyst under blue light irradiation. This unprecedented dual organocatalytic system allows the use of low catalytic loading of both catalysts under very mild operating conditions.

Regiodivergent Hydration-Cyclization of Diynones under Gold Catalysis

Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.

Synthesis of γ-pyrones via decarboxylative condensation of β-ketoacids

Abstract: This manuscript describes the convergent synthesis of aryl- and alkyl-disubstituted γ-pyrones from β-ketoacids. The reaction proceeds in the presence of trifluoromethanesulfonic anhydride via an unprecedented decarboxylative auto-condensation of the starting material. Herein, the scope and limitations of this transformation are reported. Graphical abstract: [Figure not available: see fulltext.]

Redesign of a Pyrylium Photoredox Catalyst and Its Application to the Generation of Carbonyl Ylides

We report the exploration into photoredox generation of carbonyl ylides from benzylic epoxides using newly designed 4-mesityl-2,6-diphenylpyrylium tetrafluoroborate (MDPT) and 4-mesityl-2,6-di-p-tolylpyrylium tetrafluoroborate (MD(p-tolyl)PT) catalysts. These catalysts are excited at visible wavelengths, are highly robust, and exhibit some of the highest oxidation potentials reported. Their utility was demonstrated in the mild and efficient generation of carbonyl ylides from benzylic epoxides that otherwise could not be carried out by current common photoredox catalysts.

Atom-economic synthesis of 4-pyrones from diynones and water

Transition-metal-free synthesis of 4-pyrones via TfOH-promoted nucleophilic addition/cyclization of diynones and water has been developed. This transformation is simple, atom economical and environmentally benign, providing rapid and efficient access to s

Bronsted acid catalyzed and NIS-promoted cyclization of diynones: Selective synthesis of 4-pyrone, 4-pyridone, and 3-pyrrolone derivatives

Bronsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Bronsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions.

Synthesis of novel imidazolium and benzimidazolium salts from halomethyl derivatives of 4-pyrones

A series of mono- and bis-benzimidazolium and imidazolium salts of 4-pyrone derivatives has been synthesized in good yields, by various quaternization reactions of halomethyl derivatives of 4H-pyran-4-ones. These salts can be used as novel precursors of functionalized N-heterocyclic carbenes and some of them as novel ionic liquids.

Synthesis of some Schiff Bases of 3-Aroyl-6-aryl-4-hydroxy-2 H-pyran-2-ones

The reaction of 3-aroyl-6-aryl-4-hydroxy-2 H-pyran-2-ones (Ar = p-tolyl, 1,1'-biphenyl-4-yl or thienyl) with aniline and substituted o-phenylenediamine (R = H, CH3 or Cl) yields a series of new Schiff bases 2a-f in 51-72 percent yield.Bromination of 1a ga