6275-80-5Relevant academic research and scientific papers
Absence of toxicity in Swiss mice following treatment with 7-acetoxy-4-aryl-3,4-dihydrocoumarin: Acute and repeated-dose toxicity study
Saldanha, Gláucio Barros,Saldanha, Glaucia Barros,de Sousa, Marina Rebeca Soares Carneiro,Oliveira, George Laylson da Silva,da Silva, Ana Paula dos Santos C.L.,David, Jorge M.,David, Juceni Pereira
, p. 75 - 82 (2018/02/14)
Neoflavonoids, which are classified as 4-arylcoumarin (neoflavone), 3,4-dihydro-4-arylcoumarin and neoflavene, have been the subject of a number of studies with respect to their therapeutic potential and, despite promising in vitro, ex vivo and in vivo ph
Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
Naik, Mayuri M.,Kamat, Durga P.,Tilve, Santosh G.,Kamat, Vijayendra P.
, p. 5221 - 5233 (2014/07/08)
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
Naik, Mayuri M.,Kamat, Durga P.,Tilve, Santosh G.,Kamat, Vijayendra P.
, p. 5221 - 5233 (2014/12/10)
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.
The reactions of phenols with α,β-unsaturated aromatic acids in presence of polyphosphoric acid: Synthetic and mechanistic studies
Majumder,Chatterjee,Mukhoti
, p. 743 - 755 (2007/10/03)
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.
Microwave-assisted synthesis of derivatives of chromanones
Barbry,Champagne
, p. 78 - 79 (2007/10/03)
A variety of chromanones are prepared from resorcinol and phloroglucinol in four steps: two of these reactions are conducted under microwave irradiation, the synthesis of cinnamic acids and the cyclisation of N-cinnamoylazoles.
Condensation of phenols with alkylcinnamates in the presence of FeCl3
Das,Venkataiah,Ravindranath
, p. 556 - 557 (2007/10/03)
Ferric chloride catalyses the condensation of phenols with alkylcinnamates to produce 3,4-dihydro-4-arylcoumarins.
Highly Efficient and Single Step Synthesis of 4-Phenylcoumarins and 3,4-Dihydro-4-phenylcoumarins over Montmorillonite K-10 Clay, under Microwave Irradiation
Singh, Jasvinder,Kaur, Jasamrit,Nayyar, Sandeep,Kad, Goverdhan L.
, p. 280 - 281 (2007/10/03)
A simple, elegant and one-pot synthesis of 3,4-dihydro-4-phenylcoumarins, 4-phenylcoumarins and their derivatives by making use of solid support, montmorillonite K-10 clay in conjunction with microwave irradiation is described.
α, β-Unsaturated N-Acylureas as Useful Intermediates for the Synthesis of Indanones, Chromanones and Coumarins
Ramana, M. M. V.,Kudav, N. A.
, p. 339 - 341 (2007/10/02)
α,β-Unsaturated N-acylureas, viz-N-formamido-2-butenamide (I), N-formamido-3-methyl-2-butenamide (II) and N-formamido-3-phenyl-2-propenamide (III) react with aryl alkyl ethers in the presence of PPA to afford the corresponding crotonophenones and chalcones (IV) at lower temperature and 1-indanones (V) at a higher temperature.Reactions of I and II with phenols in the presence of PPA afford the 4-chromanones (VI), while III gives 3,4-dihydro-4-phenylcoumarins (VII) in excellent yields.
