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.
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.
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.
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.
