57322-71-1

Upstream product

• 621-82-9 Cinnamic acid 
• 123-31-9 hydroquinone 
• 140-10-3 (E)-3-phenylacrylic acid 
• 150-76-5 4-methoxy-phenol 
• 102-92-1 cinnamoyl chloride 
• 22129-66-4 4-hydroxyphenyl cinnamate 
• 22867-46-5 4'-methoxyphenyl cinnamate 

Downstream Products

• 107203-64-5 (+/-)-6-acetoxy-4-phenyl-3,4-dihydrocoumarin 

Relevant academic research and scientific papers

Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling

Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation- esterification process at 120-130°C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2- ones were obtained in 5-85% yields.

Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling

Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 °C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields.

Solvent-free synthesis of 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling of phenols with cinnamic acid catalyzed by molecular iodine

Molecular iodine was used as a catalyst in the [3+3] cyclocoupling of phenols and cinnamic acids which proceeds via a tandem esterification- hydroarylation process at 120-130 °C under solvent-free conditions. Substituted 4-aryl-3,4-dihydrobenzopyran-2-one

Selective synthesis of 3,4-dihydrocoumarins and chalcones from substituted aryl cinnamic esters

Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by TiCl4. This method can be used for preparing various coumarin & chalcone compounds.

Synthetic and novel biocatalytic resolution studies on (±)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins

Eleven (±)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins have been synthesised in two steps starting from the coupling of cinnamic acid/substituted cinnamic acid with appropriate phenols, followed by acetylation in 50-83% overall yields. All hydroxy- and acet

The reactions of phenols with α,β-unsaturated aromatic acids in presence of polyphosphoric acid: Synthetic and mechanistic studies

The reactions of cinnamic acid with phenol itself, catechol, hydroquinone, pyrogallol and 2-naphthol in presence PPA were studied and that with resorcinol was reinvestigated. With phenol itself and hydroquinone were obtained 3,4-dihydro-4-phenylcoumarin (1r) and 6-hydroxy-3,4-dihydro-4-phenylcoumarin (1s), respectively, as the sole products. Catechol and pyrogallol, on the other hand, afforded, besides the corresponding 3,4-dihydrocoumarins, viz. 8-hydroxy-3,4-dihydro-4-phenylcoumarin (1t) and 7,8-dihydroxy-3,4-dihydro-4-phenylcoumarin (1u), as the major products, 5,6-dihydroxy-3-phenylindanone (5b) and the chalcone 1-(2′,3′,4′-trihydroxy)-3-phenylpropan-2-en-1-one (3d), respectively, as minor products. But contrary to earlier observation, resorcinol was found to give 7-hydroxy-3,4-dihydro-4-phenylcoumarin (1v) instead of 7-hydroxyflavanone (4e). 2-Naphthol, on the other hand, afforded the chalcone derivative 1-|2′-hydroxynaphthyl|-3-phenylpropan-2-ene-1-one (7) as the exclusive product. The yields of the major products in the above reactions were 50-67% except that with phenol itself yielding 1r in 40% yield. The structures of all the products 1r, 1s, 1t, 1u, 1v, 3d, 5b and 7 were established from their various spectral (IR, 1H and 13C NMR and mass) data. Evidence for plausible mechanisms of formation of the above products was provided.

3,3-DIPHENYLPROPYLAMINES AND PHARMACEUTICAL COMPOSITIONS THEREOF

Novel 3,3-diphenylpropylamines of formula (I) wherein R1 signifies hydrogen or methyl, R2, R3 and R4 independently signify hydrogen, methyl, methoxy, hydroxy, carbamoyl, sulphanoyl or halogen, and X represents a tertiary amino group -NR5, R6, wherein R5 and R6 signify non-aromatic hydrocarbyl groups, which may be the same or different and which together contain at least three carbon atoms, and which may form a ring together with the amine nitrogen, their salts with physiologically acceptable acids and, when the compounds can be in the form of optical isomers, the racemic mixture and the individual enantiomers, their use as drugs, especially as anticholinergic agents, their use for preparing an anticholinergic drug, pharmaceutical compositions containing the novel amines, and methods for preparing the same