162012-30-8

Upstream product

• 124-38-9 carbon dioxide 
• 960-16-7 tributylphenylstannane 
• 329328-49-6 3-bromo-4-(4'-methylthiophenyl)-5H-furan-2-one 
• 98-80-6 phenylboronic acid 
• 487047-30-3 3-chloro-4-(4'-methylthiophenyl)-5H-furan-2-one 
• 103-82-2 phenylacetic acid 
• 42445-46-5 2-bromo-1-(4-methylsulfanyl-phenyl)-ethanone 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 210292-04-9 (4-methylsulfanylphenyl)magnesium chloride 
• 108154-64-9 3-Phenyl-4-p-chlorophenyl-2(5H)-furanone 
• 108154-63-8 3-Phenyl-4-p-bromophenyl-2(5H)-furanone 
• 1778-09-2 4-(Methylthio)acetophenone 

Downstream Products

• 162011-90-7 rofecoxib 
• 745820-44-4 4-(4-(methylsulfinyl)phenyl)-3-phenylfuran-2(5H)-one 
• 1378303-49-1 C₂₃H₂₀N₂O₂S 
• 1378303-48-0 sulfiliminium mesitylenesulfonate salt 
• 866336-10-9 thiobutyric acid S-[4-(5-oxo-4-phenyl-2,5-dihydro-furan-3-yl)-phenyl] ester 

Relevant academic research and scientific papers

PURIFIED FORMS OF ROFECOXIB, METHODS OF MANUFACTURE AND USE

The subject matter disclosed herein relates to rofecoxib, also known as TRM-201 or RXB-201, its method of manufacture, and use. In certain aspects, the highly pure or substantially pure rofecoxib as provided herein has a favorable purity profile and is the active ingredient in a pharmaceutical composition that is administered to treat or prevent a number of conditions, including pain associated with a condition caused by a bleeding disorder.

Selective Late-Stage Oxygenation of Sulfides with Ground-State Oxygen by Uranyl Photocatalysis

Oxygenation is a fundamental transformation in synthesis. Herein, we describe the selective late-stage oxygenation of sulfur-containing complex molecules with ground-state oxygen under ambient conditions. The high oxidation potential of the active uranyl cation (UO22+) enabled the efficient synthesis of sulfones. The ligand-to-metal charge transfer process (LMCT) from O 2p to U 5f within the O=U=O group, which generates a UV center and an oxygen radical, is assumed to be affected by the solvent and additives, and can be tuned to promote selective sulfoxidation. This tunable strategy enabled the batch synthesis of 32 pharmaceuticals and analogues by late-stage oxygenation in an atom- and step-efficient manner.

Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx and Arcoxia

The preparation of the sulfoxide analogues 2 and 4, and their enantiomeric pure forms is discussed as well as their potential to act as prodrugs to the potent and selective sulfone-containing COX-2 inhibitors rofecoxib and etoricoxib. Sulfoxides 2 and 4 w

METHOD FOR PREPARING PHENYL HETEROCYCLES AS CYCLOOXYGENASE-2 INHIBITOR

The present invention relates to a method for preparing phenyl heterocycle as cyclooxygenase-2 inhibitor useful in the treatment of other cyclooxygenase meditated diseases, which is environmentally harmonious and has an improved productivity. More particularly, it relates to a method for preparing phenyl heterocycle as cyclooxygenase-2 inhibitor, characterized in providing a high-purity compound of Formula 5 with the low cost of production and a simple process, which is harmless to human and environmental pollution due to not generating a halogen gas when preparing, and comprising the steps of lactonization reaction with a compound of Formula 1 as an initiator; substitution reaction; and oxidation reaction.

Preparation of aryl-substituted butenolides using mucohalic acids

Methods and materials for preparing 3-aryl-2-buten-4-olides and 2,3-bisaryl-2-buten-4-olides are disclosed. The methods include reacting a mucohalic acid with a reducing agent to give a 2,3-dihalo-2-buten-4-olide, which undergoes at least one Pd catalyzed cross-coupling reaction with an arylboronic acid.

A general method for the synthesis of aryl [11C]methylsulfones: Potential PET probes for imaging cyclooxygenase-2 expression

A general one-pot method has been developed for the conversion of an aryl thiol moiety masked as the butyrate ester to the corresponding 11C-labeled methylsulfone group. The potential of this methodology has been demonstrated by the successful radiosynthesis of carbon-11 analogues of several highly selective cyclooxygenase-2 (COX-2) inhibitors such as Rofecoxib, Etoricoxib, and 3-(4-methylsulfonylphenyl)-4-phenyl-5-trifluoromethyl isoxazole in high yield. The chemical and radiochemical purities obtained for the 11C-labeled COX-2 inhibitors are >99% with a specific activity >1000 Ci/mmol.

3-PHENYLFURAN-2-ONE DERIVATIVES AS COX-2 INHIBITOR

The present invention relates to 3-phenylfuran-2-ones of formula (I), processes for their preparation, pharmaceutical compositions containing them, and their medical uses.

Mucochloric acid: A useful synthon for the selective synthesis of 4-aryl-3-chloro-2(5H)-furanones, (Z)-4-aryl-5-[1-(aryl)methylidenel-3-chloro-2(5H)-furanones and 3,4-diaryl-2(5H)-furanones

3,4-Dichloro-2(5H)-furanone, which has been prepared efficiently from mucochloric acid, has been transformed selectively into 4-aryl-3-chloro-2(5H)-furanones either by Suzukior Stille-type reactions. These monochloro derivatives have been used as precursors either to (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones, including naturally occurring rubrolide M, or to unsymmetrical 3,4-diaryl-2(5H)-furanones. Some 2(5H)-furanone derivatives so prepared have been found to exhibit significant cytotoxic activity in vitro against the NCI three-cell-line panel, but limited cytotoxicity against the NCI human tumor 60 cell-line panel. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Reinvestigation of mucohalic acids, versatile and useful building blocks for highly functionalized alpha,beta-unsaturated gamma-butyrolactones.

[reaction: see text] Mucohalic acids (mucochloric acid (1, 3,4-dichloro-5-hydroxy-5H-furan-2-one) and mucobromic acid (2, 3,4-dibromo-5-hydroxy-5H-furan-2-one)) are inexpensive, commercially available starting materials with multiple functional groups. These compounds have been modified by way of reduction followed by Suzuki cross-coupling reactions involving arylboronic acids to afford highly functionalized alpha,beta-unsaturated gamma-butyrolactones in excellent yield. The synthetic utility of these building blocks was effectively demonstrated through preparation of the antiinflammatory drug Vioxx.

Magnesium mediated carbometallation of propargyl alcohols: Direct routes to furans and furanones

The addition of vinyl and aryl Grignard reagents to propargyl alcohols for the direct synthesis of furans and butenolides from a one pot reaction is described. These products arise from a putative magnesium chelate intermediate 2 upon reaction with various electrophiles. This chelate was also generated in situ from alkynyl lithium addition to aldehydes followed by magnesium exchange and Grignard addition. Thus, the complete substitution pattern for the furan ring may be controlled, as desired, through the judicious choice of substrates and reagents.