93198-69-7Relevant academic research and scientific papers
Palladium-Catalyzed C?H Functionalization of Phenyl 2-Pyridylsulfonates
Li, Bin,Guo, Dong-Dong,Guo, Shi-Huan,Pan, Gao-Fei,Gao, Ya-Ru,Wang, Yong-Qiang
, p. 130 - 144 (2017/01/06)
An efficient palladium(II)-catalyzed intermolecular direct ortho-alkenylation and acetoxylation of phenols has been developed. The reaction proceeded via a seven-membered cyclopalladated intermediate and showed complete regio- and diastereoselectivity. The approach also provided an efficient route for the synthesis of coumarins and benzofurans.
Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
Boeck, Florian,Blazejak, Max,Anneser, Markus R.,Hintermann, Lukas
supporting information, p. 1630 - 1636,7 (2020/09/14)
(E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-nbutylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60-70 °C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph3P=CHCO2Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.
Facile preparation of bicyclo[2.2.2]octenone derivatives via Diels-Alder cycloadditions of in situ-generated masked o-benzoquinones
Kalogiros, Christos,Hadjiarapoglou, Lazaros P.
experimental part, p. 3216 - 3225 (2011/05/30)
Diels-Alder cycloadditions of in situ-generated, substituted 2,2-dimethoxycyclohexa-3,5-dienones with olefinic dienophiles resulted in the development of an efficient method for the preparation of highly functionalized bicyclo[2.2.2]oct-5-en-2-ones with g
Organophosphorus chemistry 32. 1 The reaction of vanillin, ortho-vanillin and piperonal with stabilized methylenetriphenylphosphoranes (wittig reagents)
Hafez, Taghrid S.,Henary, Maged M.,Mahran, Mohamed Refat H.
, p. 33 - 44 (2007/10/03)
Vanillin (1) and piperonal (3) reacted with ylidenetriphenylphosphoranes 4a-f in boiling toluene following the Wittig mechanism to give the ethylenes 5a-f and 7a-f. Similarly, ethylenes 8c-f were produced when ortho-vanillin (2) was allowed to react with 4c-f. The reaction of aldehyde (2) with the P-ylides 4a,b yielded the Wittig products 8a,b and 8-methoxycoumarin (10). Triphenylphosphine oxide (TPPO, 6) was isolated and identified in all cases. The mechanism for formation of 10 was discussed. Structural reasonings for all new compounds were based upon compatible elementary as well as spectroscopic (IR, 1H-NMR and MS) measurements.
