67075-01-8

Upstream product

• 67300-96-3 5-acetyl-6-hydroxy-4-(4-methoxyphenyl)-2H-pyran-2-one 
• 7647-01-0 hydrogenchloride 
• 67075-05-2 4-(4-methoxyphenyl)-2-methyl-6-oxo-2H-pyran-3-carboxylic acid 
• 5720-07-0 4-methoxyphenylboronic acid 
• 132559-91-2 4-bromo-6-methyl-2H-pyran-2-one 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 31913-41-4 6-methyl-4-tosyloxy-2(2H)-pyranone 
• 1250880-92-2 C₁₁H₁₀O₂ 
• 1364680-89-6 C₁₄H₁₆O₄ 

Downstream Products

• 93098-18-1 1,2-dihydro-5-(4-methoxyphenyl)-7-methyl-1-phenyl<1,2>diazepin-3-one 
• 99391-04-5 4-(4-Methoxyphenyl)-6-methyl-2H-pyran-2-thione 
• 93098-15-8 1,2-dihydro-5-(4-methoxyphenyl)-7-methyl<1,2>diazepin-3-one 
• 67075-08-5 1,2-Dihydro-4-(4-methoxyphenyl)-6-methyl-2-pyridinone 
• 99390-99-5 1-Hydroxy-4-(4-methoxy-phenyl)-6-methyl-1H-pyridin-2-one 
• 99391-00-1 1-Amino-4-(4-methoxyphenyl)-6-methyl-2(1H)-pyridinone 
• 99391-06-7 3-Bromo-4-(4-methoxyphenyl)-6-methyl-2H-thiopyran-2-one 
• 99391-02-3 1-(2-Aminoethyl)-4-(4-methoxyphenyl)-6-methyl-2(1H)-pyridinone 
• 99391-03-4 3-(4-Methoxyphenyl)-1-methylpyrido<1,2-a>benzaimidazole 
• 99390-97-3 1-benzyl-4-(4-methoxyphenyl)-6-methyl-1H-pyridin-2-one 
• 99391-01-2 4-(4-Methoxyphenyl)-6-methyl-1-phenylamino-2(1H)-pyridinone 
• 99390-98-4 1-(4-Chloro-phenyl)-4-(4-methoxy-phenyl)-6-methyl-1H-pyridin-2-one 
• 99391-05-6 4-(4-Methoxyphenyl)-6-methyl-2H-thiopyran-2-one 

Relevant academic research and scientific papers

Environmentally sustainable and chemo-selectively favorable synthesis of substituted 2H-Pyran-2-ones in water under MWI

In this paper, a novel synthesis of diversely substituted 2H-pyran-2-ones via the tandem reaction of 3-hydroxyhexa-4,5-allenic esters in water under the promotion of MWI has been developed. Compared with those reactions carried out in organic solvents, wa

[Pd(PPh3)2 (saccharinate)2]- general catalyst for Suzuki-Miyaura, Negishi cross-coupling and C-H bond functionalization of coumaryl and pyrone substrates

The potential of complex [Pd(PPh3)2(saccharinate) 2] 1 in catalyzing Suzuki-Miyaura cross-coupling of 4-halo and 4-bromomethyl coumaryl and pyrone substrates with different aryl boronic acids has been explored. Excellent yields of the desired products are obtained in competitive reaction time and under relatively mild conditions. Negishi cross-coupling of 4-coumaryl tosylate with aryl and alkylzinc reagents has also been performed with good yields of the cross-coupled products obtained in most cases. Intra-molecular C-H bond functionalization of coumaryl ethers also furnished very high yields of synthetically attractive tetracyclic ring systems exhibiting the potential of 1 as a powerful catalyst in synthetically important reactions.

Tandem reaction of 3-hydroxyhexa-4,5-allenic esters: A novel access to diversely substituted 2H-pyran-2-ones and indenes

A highly efficient synthesis of diversely substituted 2H-pyran-2-ones and indenes through Bronsted acid promoted tandem reaction of the readily obtainable 3-hydroxyhexa-4,5-allenic esters under extremely mild conditions has been developed. The Royal Society of Chemistry 2012.

Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C-OH bond activation

An efficient palladium-catalyzed cross-coupling reaction of 4-hydroxy-pyrone or 4-hydroxy-2(5H)-furanone with arylboronic acid is described, which affords the 4-substituted-pyrones and 2(5H)-furanones in good yields. This transformation proceeds through a C-OH bond activation under mild conditions.

An efficient route to 4-substituted coumarins, 2(5H)-furanones, and pyrones via palladium-catalyzed couplings of alkenyl tosylates with organoindium reagents

Highly efficient palladium-catalyzed couplings of alkenyl tosylates with organoindium reagents under mild conditions are described, which give rise to 4-substituted coumarins, 2(5H)-furanones, and pyrones in good to excellent yields.

N-heterocyclic carbene derived Nickel-Pincer complexes: Efficient and applicable catalysts for Suzuki-Miyaura coupling reactions of aryl/alkenyl tosylates and mesylates

Catalytic activities of NHC-derived nickel-pincer complexes for the Suzuki-Miyaura coupling reactions of aryl/alkenyl to- sylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class of electrophiles was achieved only by choosing the appropriate reaction medium (DME for tosylates, dioxane for mesylates).

An economical access to 3,4-diaryl-2(5H)-furanones and 4-aryl-6-methyl- 2(2H)-pyranones by pd-catalyzed Suzuki-type arylation of 3-aryl-4-tosyloxy-2(5H) -furanones and 6-methyl-4-tosyloxy-2(2H)-pyranones, respectively

Both symmetrical and unsymmetrical 3,4-diaryl-substituted 2(5H)-furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)2/PCy3-catalyzed Suzuki-type arylation of readily available 3-aryl-4-tosy

2-Pyrones possessing antimicrobial and cytotoxic activities

The 2-pyrone sub-unit is found in a number of natural products possessing broad spectrum biological activity. Such compounds are validated as being capable of binding to specific protein domains and able to exert a remarkable range of biological effects. In an effort to identify synthetic 2-pyrones with interesting biological effects, herein we report the synthesis and biological evaluation of 4-substituted-6-methyl-2-pyrones. Synthetic routes to 4-alkyl/alkenyl/aryl/alkynyl-6-methyl-2-pyrones have been developed utilising Sonogashira, Suzuki and Negishi cross-coupling starting from readily available 4-bromo-6-methyl-2-pyrone. Specific conditions for each organometallic protocol were required for successful cross-coupling. In particular, a triethylamine/acetonitrile - base/solvent mixture was crucial to Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone, whereas thallium carbonate was a mandatory base for the Suzuki cross-coupling of trialkylboranes. The 2-pyrones demonstrate potent inhibitory activity against Bacillus subtilis, Escherichia coli, Staphylococcus aureus, Schizosaccharomyces pombe and Botrytis cinerea. The growth inhibitory activities of selected 2-pyrones were determined in A2780 human ovarian carcinoma and K562 human chronic myelogenous leukaemia cell lines using an in vitro cell culture system (MTT assay). These studies demonstrate that 4-phenylethynyl-, 4-tetrahydropyranylpropargyl ether- and 4-ethynyl-6-methyl-2-pyrones have excellent potential as a new class of anticancer agents.

Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines.

Bioactive synthetic 4-substituted-6-methyl-2-pyrones are reported. Various 4-substitutents have been incorporated using Pd-catalysed carbon-carbon bond coupling procedures. Preliminary screening of the 2-pyrones against human ovarian carcinoma (A2780) and